Getting hired is not about qualifications. It is about positioning.

A message that clearly resonates as the growth of this Substack has been exponential.

Don didn’t leave the corporate world because he lacked success. He spent over a decade in marketing and Go-To-Market strategy, working in director-level roles across education and admissions. On paper, everything worked. The title. The progression. The expertise.

It was through his work that he discovered a gap that became impossible to ignore.

The problem? Thousands of capable graduates had the skills, but they had no clear way to show their value, signal relevance, or stand out in a crowded hiring process. On paper, they looked qualified. In reality, they were invisible.

Inside, Don breaks down how he turned marketing strategy into a system that sustained his own career growth whilst at the same time helping others build theirs.

He is direct about networking, personal branding, exactly what made him leave a secure role, and how he built a platform now reaching over 79,000 readers.

If you feel like you could build outside the system, then this one is for you.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

Professionals are building portfolio careers by applying their skills in more than one place, combining roles, writing, consulting, teaching, business ownership, and digital work.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher exploring how people are turning existing expertise into more resilient, future-ready careers.

This is how modern career security is being built in practice.

About Don

Don Long is the Founder and CEO of The Internship Guy, a mission-driven platform and Substack newsletter with over 79,000 subscribers.

He spent more than a decade in marketing and Go-To-Market strategy, working in director-level roles across education and admissions.

He uses his expertise to help the next generation of talent navigate the transition from education to the professional world.

His work focuses on one thing. Turning capable candidates into competitive ones.

You can follow his work here →

Don reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

If you looked at my career path a few years ago, you would have seen a classic trajectory in marketing and growth. I spent over a decade deep in the world of content production, Go-To-Market (GTM) strategy, and high-level marketing. Eventually, that path led me into director-level roles within the education and admissions industry.

I loved the strategy and the fast-paced nature of the work. However, working at the intersection of education and corporate strategy gave me a front-row seat to a massive problem. I saw thousands of students graduating with incredible degrees but absolutely no idea how to market themselves in a competitive job market. They had the talent, but they didn’t have the “playbook.”

That realization changed everything for me. I am now the Founder and CEO of The Internship Guy (TIG). What started as a mission-driven project has grown into a community of over 50,000 subscribers on Substack. We help students and early-career professionals bridge the gap between the classroom and the boardroom.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

The pivot wasn’t about running away from marketing. It was about applying everything I knew about GTM strategy to a cause that actually mattered to me. I had a slow realization that I could keep building brands for others, or I could build a platform that directly impacted the lives of young professionals.

The “mission” became the driving force. I saw too many bright minds struggling with the “experience paradox,” which is the frustrating cycle of needing a job to get experience but needing experience to get the job. I knew that with my background in admissions and marketing, I could provide the roadmap they were missing. Acting on it required leaving the comfort of a traditional director role to embrace the uncertainty of a startup, but the mission made that choice much easier.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

It turns out that ten years of marketing and GTM strategy is the perfect foundation for career coaching. Landing a dream internship is, at its core, a marketing exercise. You are the product, the recruiter is the target audience, and your resume is the conversion tool.

My director-level experience in the education sector also gave me a deep understanding of how academic institutions operate and where they often fall short. By blending high-level marketing tactics with an insider’s view of education, I was able to create content that was both strategic and highly practical. I don’t just tell students to “network.” I teach them how to build a personal brand and execute a cold outreach strategy like a professional salesperson.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I chose Substack as my primary platform because it allows for a depth of connection that social media just cannot replicate. For a mission-driven business, trust is the most important currency. When I send an email to 50,000 people, I am entering their personal space.

Substack has become the engine of my portfolio career. It acts as a newsletter, a community hub, and a launchpad for our larger initiatives. It allows me to stay lean while maintaining a massive reach. By focusing on high-value, long-form content, I’ve been able to establish TIG as a leading voice in the career development space.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My work is specifically for the “underdog” student or the career-changer who feels like the system isn’t designed for them. I solve the problem of career gatekeeping.

We provide the templates, the AI workflows, and the networking scripts that are usually only passed down in elite circles. People find value in TIG because we don’t give generic advice. We give actionable blueprints that lead to real-world results, like landing a role at a top-tier tech firm or a prestigious consulting group.

“What turned out to be harder than you expected when you started… and what was easier than you imagined?”

The hardest part of this journey was the transition from “Director” to “Founder.” In a corporate role, you have a team and a safety net. As a founder, especially in the early days, you are the marketing department, the customer service team, and the content creator all at once.

What was easier than expected was the growth. I found that when you lead with a mission and provide genuine value, people become your best advocates. Our growth to 79,000 subscribers happened largely because our community started sharing our resources with their peers. It confirmed that the gap I saw in the market was even larger than I initially thought.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

The journey on Substack has been incredibly rewarding. If I were to give advice to others looking to grow, it would be this: consistency is your only non-negotiable. You have to show up in that inbox when you say you will.

I also recommend focusing on “collaborative growth.” Don’t view other writers as competition. View them as partners. Features like Substack Recommendations have been a game-changer for us, allowing us to reach audiences we might never have found on our own.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

For anyone considering a similar pivot, especially those coming from high-level corporate roles, I’d say: don’t leave your skills behind. Use them. If you are a great project manager, treat your pivot like a project. If you are a marketer, market your new mission.

A portfolio career isn’t about doing five different things poorly. It is about taking one core set of expert skills and applying them across different income streams and platforms. It’s a more flexible, resilient, and ultimately more fulfilling way to work.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

Looking back, the decision to go all-in on the mission behind The Internship Guy was the best career move I ever made. It has allowed me to combine my professional expertise with a purpose that keeps me motivated every single day.

What’s next? We are continuing to scale our community and looking for new ways to make career literacy accessible to everyone. Our upcoming Zenith Career Summit is a huge part of that, and I can’t wait to see the impact it has on the thousands of students attending.

Links & Resources

Connect with Don…

→ Sign up for the Zenith Career Summit (2 for 1 ticket deal): eventbrite.com/e/zenith-career-summit-tickets-1984257293981

Register today for the global virtual career summit presented by TIG, where students and early professionals from around the world connect with top employers, educators, and AI-powered career tools.

You’ll get exclusive access to virtual sessions; $10,000+ value in free career tools, courses, and coaching; a 24/7 AI Career Coach + instant resume reviews and free 1:1 coaching sessions with world-class mentors.

→ Claim your free Big 4 consulting + 2026 internships toolkit (worth $200+)

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Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are quietly asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?

Drop it in the comments, and let’s keep the conversation going.

Alesia spent nearly two decades in academia, researching how language shapes public opinion and teaching social sciences at a university.

On paper, it was a strong career. In practice, it felt slow and disconnected. Publishing took years, feedback was limited, and as AI began to change how people work and write, the gap kept growing.

She didn’t wait to see what would happen and started learning by doing.

The next step was launching a newsletter and writing about AI in real time. No polished plan. No certainty it would work.

She tested tools, shared what she learned, and paid attention to what readers found useful. Over time, a pattern emerged. Practical, hands-on content worked and systems worked.

Grow Smarter With AI became a place to document experiments, build repeatable processes, and help others avoid trial and error.

In this Playbook, Alesia breaks down how she left academia, what actually drives growth on Substack, and how she built a system that turns knowledge into income.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Alesia

Alesia Zakharova is the writer behind Grow Smarter With AI, where she documents how professionals can use AI to support writing, marketing, and building a newsletter business.

Her background is in social research and teaching, with a focus on how language and narratives shape public opinion.

Now, she shares what she tests in real time, from prompts to workflows, with a focus on what actually works in practice.

You can follow her work here →

Grow Smarter With AI

Researcher & Writer. Testing AI tools for newsletter writers who want to automate routine tasks and focus on the creative work.

By Alesia Zakharova

Alesia reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I spent nearly 20 years teaching social sciences at a university and conducting social research, with much of my work focused on analyzing politicians’ speeches, examining the frames and narratives they used and how those shaped public opinion. I have a PhD on the subject and contributed articles to various media outlets along the way.

Over time, I started burning out. Academic life began to feel painfully slow, a single journal article can take two years from submission to publication, and I increasingly felt disconnected from the real world. When AI entered everyday life, that feeling only grew. There was also no shortage of voices claiming AI would make people like me redundant. So I decided to find out for myself.

Around the same time, I had a long-standing dream I’d never acted on: launching my own newsletter. Work and family had always gotten in the way. About a year ago, things finally aligned, I stepped away from academia and took the leap. Choosing a topic was easy; I wrote about what I was learning, which was AI. There’s no better way to learn something than to do it publicly and bring others along for the ride.

I started writing about AI’s broader societal impact, but gradually shifted toward something more hands-on — experimenting with tools, testing how they could automate marketing and business tasks, and documenting what I found. That content resonated most with readers, and my newsletter is now called Grow Smarter With AI.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

Working with Claude was the moment something clicked for me. I realized that AI, even as it exists today, is going to reshape how we write, learn, work, and think. If I wanted to stay relevant, I needed to embrace the unfamiliar and turn the page on that chapter of my life. The timing felt right.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

Two things from my academic background turned out to be unexpected strengths.

First, a research-driven approach — when I published my first article sharing a prompt for identifying the formula behind a viral note, I almost didn’t post it, worried it would come across as too dry. I was wrong. That was exactly what readers connected with.

Second, years of teaching had made me good at making complicated things feel approachable. Readers have commented more than once on how clear and doable everything felt.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I chose Substack because, a year ago — and even now — the platform was in a growth phase. Notes had just launched, conditions for organic growth were favorable, and many writers I admired were moving there. I love that it’s not just a publishing platform but a community. It’s a great place to start, because if you engage actively, you’ll find a lot of support and like-minded people. I’ve also started posting more actively on LinkedIn and am launching my own website.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My work is for professionals — coaches, lawyers, economists, teachers, psychologists, and others — who want to turn their expertise into a newsletter that pays them, whether through paid subscriptions, consulting clients, or their own products. Whether you’re just starting out or already burning out, the root problem is usually the same: no system.

Most professionals dive into content creation without one. Early on it feels manageable, but soon they’re juggling writing, marketing, audience growth, and monetization all at once. The excitement fades, burnout sets in, and the newsletter stalls.

I help writers avoid that trap from day one or escape it if they’re already there.

I know this firsthand. After 20 years as an academic researcher, I left to build my own newsletter from scratch. I had the expertise but none of the marketing or business knowledge, so I did what researchers do: I studied it, tested it, and built a system that works.

That’s what I share with my readers. My approach is research-backed and built from real experience, combining a clear framework with AI-powered prompts to automate the marketing and business side.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

One thing that proved harder than expected was building a consistent publishing schedule and sticking to it. The number of tasks that pile up is staggering: writing posts, keeping up with Notes, replying to comments, engaging with other people’s content, developing and launching a product, and staying on top of everything happening in AI. Finding balance was a real challenge.

What turned out to be easier than I feared was not giving up. I genuinely worried slow growth would wear me down. For the first three months, my subscriber count was tiny but that small audience was so engaged and enthusiastic that I never once stressed about the numbers. Writing for the people already there felt like a privilege. The slow start kept me grounded.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

I’m really enjoying my Substack journey. My main strategy is to communicate and experiment. Substack is not a platform where you can simply publish and expect readers to find you. Without engaging other writers, leaving comments, and participating in boosts, nothing moves. If two weeks pass without a new subscriber or comment, that’s a signal — try something new and see what happens.

“What nearly made you quit, and what actually kept you going?”

This hit home in January. I stalled at 900 subscribers: existing readers were leaving, comments dried up, and nothing I tried worked. For the first time, I felt genuinely lost and began questioning whether I’d chosen the right platform. I shifted focus toward LinkedIn and eased off Substack. Two weeks later, everything turned around — 200 new subscribers in a single week. That moment gave me a whole new wave of energy.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Start before you feel ready. Most of what scares you now will fade once you’re in motion — and you’ll find doors opening that you never even knew existed when you first began.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

For the past year, I was fully focused on Substack and deliberately chose not to develop other platforms, partly because I also had a lot going on with family. But now I’ve started working on LinkedIn. I’ll be experimenting and seeing how well the two work together as a pair.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

The best decision I made was diving into AI a year ago and putting it to work in marketing and building a newsletter business.

As for what’s next , I’m launching a product line and growing my consulting client base.

Links & Resources

Connect with Alesia…

On LinkedIn

Grow Smarter With AI

Researcher & Writer. Testing AI tools for newsletter writers who want to automate routine tasks and focus on the creative work.

By Alesia Zakharova

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Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

Edel spent 25 years in tech, including leading a Global Customer Insights team at Google. On paper, everything worked. In reality, something had started to shift.

She was already training in psychotherapy when that tension became harder to ignore. The move away from Big Tech didn’t happen overnight, but once it clicked, she knew it was the right move.

What followed was a transition shaped by instinct, burnout, and a different set of priorities around work, health, and family.

Inside this interview, Edel shares what led her to leave Google, how her past experience shows up in her work today, and what it’s like to build something new from the ground up.

She also talks about building on Substack without chasing the algorithm, and how she’s approaching growth, audience, and income on her own terms.

If you’re considering leaving a big role to build a more flexible way of working, this will give you a clear, honest look at what that actually takes.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals are building resilient, future-ready careers, with professionals often using Substack alongside research, consulting, teaching, creative work, or operating businesses.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Edel

Edel Grogan is a psychotherapist and writer behind From Grit to Grace, where she writes about burnout, identity, and building a life that fits who you are.

She spent 25 years in technology, including leading a Global Customer Insights team at Google, before stepping away to retrain in psychotherapy and build a different kind of career.

Drawing on her life as an Irish woman, mother, and psychotherapist, her writing blends science, story, and reflection, inviting you to move from survival mode to a life grounded in self-inquiry.

Her work sits at the intersection of psychology, lived experience, and storytelling, helping you make sense of what’s really driving how you live and work.

You can follow her work here →

From Grit to Grace with Edel Grogan

From Google to Psychotherapy, specialist in burnout, writing that brings you a little science, story and lot of soul. Supporting your journey From Grit to Grace.

Edel reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I never planned to write but I have come to understand that the words and phrases bubbling in my head have been waiting years to burst onto the page. Writing is an expression of my inner seanchaí! For those unfamiliar with that word - the seanchaí were master storytellers in Ireland preserving history and mythology. I’m not saying I’m a master storyteller, but my Dad loves to tell a story, so between my roots, culture and experience of life as an Irish woman, a mother, a wife, an IT professional, and now a psychotherapist - here I am writing on Substack.

It’s instinct and grief that led me here. I say instinct because I launched From Grit to Grace without a clear vision - just an urge to jump on a wave and trust the ride. For a long time I hushed those instincts. Now I trust more, which honestly has only come in the last 7 years - a shift influenced largely by a pivot from Google to psychotherapy and perhaps the natural process of midlife reckoning. I spent 25 years working in technology and I am now in the early stages of building my psychotherapy business.

I say grief got me here because From Grit to Grace launched in the aftermath of my aunt Bridget’s death. It was then I came to understand Bridget’s character in the context of our culture and societal influences. I felt her fearless, outspoken spirit settle in my heart. With it, came a sense of responsibility to approach my work as a therapist, with a keen eye on our patriarchal and Catholic conditioning. Bridget passed in early February, synchronous with the feast day of our Celtic pagan goddess Brigid, who is associated with healing, fire, poetry and wisdom - all themes aligned with my writing.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

It wasn’t one moment - it was a series of small moments that led to my decision to leave Google. The straw that broke the camel’s back was a small conversation where it finally landed that Google was no longer for me. Leaving was terrifying. I had worked hard to climb the corporate ladder. At Google we talk about the golden handcuffs - the unvested shares that keep you hanging on. The push was realising the future I wanted was on hold until I took action. It’s scary because you haven’t lived that future yet.

I was two years into my psychotherapy training at that stage. I could no longer ignore my body’s signals - the exhaustion, the irritability - I was burnt out, struggling with an autoimmune disease and my nervous system felt fried.

I wanted time to mother my sons, freedom to prioritise them and my own health and a schedule that fitted those priorities. While there were many aspects of work I loved, a career in Big Tech was ultimately incompatible with my values for living.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

I led a Global Customer Insights team at Google - my team conducted research, delivered insights to directors and VPs advising on product and service improvements. I’m pretty good at distilling what matters and making sense from chaos - and now I get to apply that to the human heart. I’ve never built my own business before, but I draw on the experience of my many tech hats - problem solving, success measurement, service design, process management, project management and research.

But more than that, I learned stories matter - they hit our heart, our head and our feet. To inspire others and drive change, we’ve to connect with people on a logical level - it needs to make sense, to feel in our heart it’s the right thing to do and the feet naturally take action. We don’t always need a plan. Sometimes all we need to know is the next move.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I spent my technology career in a constant think-plan-do cycle, evaluating pros and cons with frameworks and diagnostic tools. I made a decision to sign up for a Certificate in Psychotherapy in 2 days, moved into the Bachelors and eventually the Masters program. The idea came on a beach in the West of Ireland - it felt right and I followed the nudge. The decision to start Substack carried the same intuitive energy.

I find myself being pulled into the visibility trap and serving the algorithm, only to pull away again. I’m here to build something authentic, not exploit or fabricate an audience. I have just under 300 readers and a consistent 30% open rate - which I find pretty awesome.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

From Grit to Grace is for thinkers, feelers and quietly rebellious hearts who are done with the hustle. I bring readers science, story and soul - writing that encourages you to look inward and find your rooted centre. My long form posts are shaped around four themes:

• The Burnout Bulletin: Deconstructing what keeps us stuck.

• The Inner Compass: Finding your way back to yourself.

• Quiet Power: Redefining leadership and presence.

• Unfurl: The creative process of becoming.

For those wanting to go deeper I offer:

• The Forest Floor is my paid Substack tier - support the development of a therapist-led sanctuary featuring occasional workbooks and reflective prompts. Join me as we journey from grit to grace together.

• Reflective Guides - Downloadable tools to help you unpick inherited scripts and audit your own soil.

• Psychotherapy - Specialist support for adults based in Ireland. Available in my Ratoath studio or online. Book a Discovery Call.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

A few weeks ago, I attended a talk by Irish author Patrick McCabe and he spoke of the wounds all writers carry, and the search that lies between the lines. We drop blood when we write. Writing with boundaries remains an ongoing journey.

I’ve worked in performative-driven systems all my life. I can’t force myself to perform for the Substack algorithm - it goes against my grain. Honestly I haven’t yet found an authentic way to show up on notes. I ebb and flow, wax and wane - it’s easier to let things unfold in their own time. Creativity bubbles naturally from this space. It’s also hard to stay this course when performative posts and growth strategies flood the ecosystem.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

As I reflect on my year, it’s from the perspective of a budding writer that is discovering her voice.

• I’m still writing - win.

• Discovering my voice - win.

• Finding new shoots in poetry - surprise.

• And humbled by 30% open rates.

I’m in the business of authenticity, so staying in this energy is hugely important to me.

If I was in the business of marketing and growth strategies, I may have different advice about growth.

But we are all in the business of connection and relatability. This is at the heart of all writers.

I’m not growing at the expense of my authenticity and I’m still figuring out what that looks like.

“What nearly made you quit, and what actually kept you going?”

Quitting hasn’t come up. I’m riding this wave and wondering what shore I’ll land on.

I’ve more to say, more to contribute, hearts to connect with, minds to inspire.

I’m not done!

This is a movement.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Believe in the impossible. The word itself says: I’m possible.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

I launched my psychotherapy business in January so most of my income comes from individual sessions, with plans afoot for diversification. I have recently shaped a paid Substack offering and look forward to welcoming new subscribers to The Forest Floor.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

One decision changed everything: leaving certainty behind. Walking away from a career I had spent 25 years building was terrifying, but it created space for a life aligned with my values.

What’s next is continuing to grow my psychotherapy practice, deepening my writing on Substack, and building spaces where people can explore identity, healing and transformation.

Links & Resources

Connect with Edel…

• The Grace Tree | Psychotherapy

• Edel Grogan | LinkedIn

• Underthegracetree | Instagram

From Grit to Grace with Edel Grogan

From Google to Psychotherapy, specialist in burnout, writing that brings you a little science, story and lot of soul. Supporting your journey From Grit to Grace.

Related Articles

Four themes shape my writing -

The Burnout Bulletin, The Inner Compass, Quiet Power & Unfurl.

This is a great place to start navigating the archive of my work Welcome to From Grit to Grace.

Read More

Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

Rob didn’t start as a creator. He built his career in finance and construction management, working on high-value projects while figuring out business on the side.

But that pull toward entrepreneurship he had deep down never left.

So he started building the foundations of an online business. Writing, posting, launching, and growing whilst steadily improving the skills that would drive real results.

The real gear shift happened when he changed how he showed up online, invested in the right support, and focused on a specific problem he understood deeply.

Inside this interview, Rob breaks down the moments that forced him to rethink his approach, what finally started working, and how he turned those early wins into a full-time business.

He gets into what most creators get wrong about growth, why positioning matters more than content, and how small changes can unlock outsized results.

If you are building on Substack and feel stuck between effort and traction, this one will give you a clearer path forward.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Rob

Rob Riker helps Substack creators become the kind of person other creators want to know.

He built a 34,000-person audience on Twitter and a six-figure coaching business by focusing on positioning, relationships, and clear offers.

Today, he teaches Substack creators how to stand out, attract the right people, and turn their audience into paying clients.

His work has been featured in Business Insider, Lifehack, and Tiny Buddha.

You can follow his work here →

The Creator's Edge

The playbook for Substack creators who are doing the work but not getting noticed.

By Rob Riker

Rob reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I graduated in 2009 with a finance degree and went straight into portfolio management, managing over a hundred million dollars in commodity ETFs. After two years I moved to an engineering firm where I spent the next decade doing construction management and project controls on about half a billion dollars worth of work.

But ever since reading Rich Dad Poor Dad in high school, I had this desire for entrepreneurship that never went away. So in 2015, I bought a course on building an online business and chose social skills as my niche because I’d spent years overcoming my own struggles with it, and finally built the social life I wanted. I spent five years building an email list, writing guest posts, trying to sell courses. I worked hard, but the money was minimal.

In 2018, I got on Twitter. For two years I struggled with the same thing a lot of creators struggle with: putting in the work and not seeing it pay off. Then in 2020, a friend helped me see what I was doing wrong. I changed how I was showing up, and my audience actually started to grow.

Around the same time, I hired a coach who helped me create a high-ticket social skills coaching program. Eight weeks later, I’d made nearly $10,000. Then friends started asking how I was selling coaching so well and offered to pay me to help them. That became a business helping coaches build coaching businesses. It got me well past six figures, and in 2022 I was able to leave my 9-to-5 and go full-time.

In 2025, I found Substack and knew it was where I wanted to build next. I brought my relationship-building and positioning expertise to the platform, and now I help Substack creators stand out, build real relationships, and position themselves as someone people actually want to follow and connect with. My product, The Magnetic Substacker, is the system I built around everything I’ve learned.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

Two moments that built on each other.

Before I ever bought a course, I tried selling rap beats online. I built a website, figured out the tech, put them up, and then realized I had absolutely no idea how to actually sell anything. That was the first moment where I thought, “This is never going to work unless I learn how to do this for real.” That led me to buying Ramit Sethi’s Zero to Launch course in 2015.

The second was after putting 5 years of real effort into Ramit’s course. It gave me a strong foundation of online skills, but the money still wasn’t there. And I had this moment where I realized if I just kept doing what I’d been doing, nothing was going to change. So I invested $4,000 in my first coach, and that’s when everything finally started moving.

The common thread is recognizing when you’ve hit the ceiling of what you can figure out alone. I don’t think courses or coaches are magic pills, it needs to be the right thing at the right time. But, for me, the right ones compressed years of trial and error into weeks.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

1 — The people skills I taught myself. I spent years studying what makes people connect, out of genuine need because I struggled with it. But once I started applying those skills to my business, everything changed. Understanding how people think, what makes them trust you, what makes them want to connect, that’s the foundation of everything I do now.

2 — My analytical brain. A decade of portfolio management and project controls taught me how to read data and find patterns. That’s become a huge advantage as a creator. It helps me figure out what’s actually working versus what just feels like it’s working, and it’s helped me pivot when I emotionally didn’t want to.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I’ve always chosen platforms based on where I genuinely enjoy spending time. I started writing on Twitter in 2018, and it worked because I actually loved being there. I tried Instagram and it never stuck because I just don’t enjoy using it. Early on, you need to be social on social media. If you don’t even want to open the app, you’re fighting an uphill battle.

In September 2025, I found Substack. It’s kind of what Twitter used to be, but more positive and more focused on actual ideas. The way notes connect to the blog, and how the blog connects to the email list, the whole ecosystem is really special. And the culture is incredibly positive.

My main audiences are on Twitter (34,000 followers), Substack (around 1,500 followers), and my email list (around 1,100 subscribers).

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

Smaller Substack creators who have some traction but are struggling to make the next leap. They’re typically at 100 to 300 subscribers. They’ve got some engagement going, but they’re gaining maybe 5 to 10 subscribers a month, and the bigger creators they want to connect with aren’t really connecting back.

The problem I solve is positioning. I help them position themselves as someone people want to follow, connect with, and even pay for help. When that positioning is dialled in, everything else starts working better. The Magnetic Substacker is the product I built around this.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

The hardest thing was finding where my audience hangs out and getting my message in front of them. With social skills content, there was no obvious place where those people were gathered. Finding product-market-platform fit can be difficult.

What surprised me was how much easier it was to sell high-ticket offers than I expected. I spent months building courses and writing launch sequences, and I’d make a few hundred dollars. Then I launched high-ticket coaching (with way less effort) to roughly the same size audience and made nearly $10,000 in the first few weeks. Same number of people, wildly different revenue. Selling something expensive isn’t necessarily harder. It just has to be the right offer for the right person.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

I’m having an absolute blast. The connections I’m making on Substack are unlike anything I’ve experienced on other platforms. Real conversations, real friendships, not just surface-level engagement.

My biggest tip is something most people overlook: your bio and profile matter way more than you think. I changed my bio and my subscriber growth more than 12X’d. Same content, same engagement, just a clearer message about who I am and who I help. If your profile sends any subtle signal that tells someone, “You’re not for me,” they won’t subscribe, and your growth is going to be painfully slow. Getting that right is more valuable than almost anything else you can do.

“What nearly made you quit, and what actually kept you going?”

Those first five years when progress was painfully slow. I’d spend months building a product, then another month on launch logistics, and then make a few sales. It was brutal.

What kept me going was this deep desire to help people. And I’ll be honest, I also wanted financial freedom and the flexibility to live the way I want.

But helping people really lights me up. When I was doing social skills content, I had a post go viral on Reddit and hundreds of people responded saying how helpful it was. That filled me so deeply.

Even now, it feels amazing when someone overcomes that frustration of grinding and not making progress. You can see the emotion in their eyes, hear it in their voice, and read it in their words. Those moments kept me going in the beginning, and they keep me going today.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Get really specific about the problem you’re going to solve.

A lot of people take a skill set and try to sell it broadly. They think, “I struggled with my goals and then I hit some of them, so now I’ll help people with their goals.” I’ve tried that. It doesn’t work well.

What does work is getting specific about one small, concrete problem.

My latest product is a great example. I built it because Substack creators are frustrated with putting in effort and having slow growth. And I solved that by helping them create a profile and positioning that makes them look attractive, competent, and worth connecting with. That specific problem to specific solution is way more powerful than trying to sell some big transformation.

You just need to solve a real problem that you’ve actually solved for yourself. That’s what gives you the credibility to charge for it.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

My main audiences are on Twitter (34,000 followers), Substack (around 1,500 followers), and my email list (around 1,100 subscribers).

“Looking back, what’s one decision that changed everything… and what’s next for you?”

Betting on myself. And it’s not a one-time decision. I bet on myself when I bought that first course in 2015. I bet on myself every time I hit publish. I bet on myself every time I invest in a coach.

What’s next is helping more people succeed on Substack. More people every year are entering the creator space, and the opportunity is real, but it’s harder than a lot of people make it sound. The creators I help most often have some traction but haven’t cracked consistent growth yet. I help them grow faster, position themselves correctly, and start making real sales. That’s exactly what I’m continuing to build.

Links & Resources

Connect with Rob…

Website: robriker.com

Product: The Magnetic Substacker

The Creator's Edge

The playbook for Substack creators who are doing the work but not getting noticed.

By Rob Riker

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Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

She didn’t come from a technical background. Her career path started in retail management, then dramatically shifted after a major life change forced her to rethink how she worked and lived.

She moved into online business with no clear roadmap and figured it out by doing.

Inside this interview, Kim shares what that transition actually looked like, the patterns she started to notice, and how her earlier experience began to work in her favor.

She breaks down how she built her brand through content and podcasting, what helped her create multiple income streams, and how she is now using AI in practical ways inside her business.

If you are trying to build something sustainable, on your terms, without feeling “technical enough,” this one is for you.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals are building resilient, future-ready careers, with professionals often using Substack alongside research, consulting, teaching, creative work, or operating businesses.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Kim

Kim Doyal is an AI strategist and online business owner who shows you how to build with AI without a technical background.

She spent over 17 years building online, creating offers, content, and systems that generate real income while supporting her life.

Today, she teaches how to use AI to save time, create your own tools, and turn your experience into something people will pay for.

You can follow her work here →

Kim Doyal

Build AI-powered solutions without a coding degree. After 17+ years online, I'm showing you how to use AI to save time, scale smarter, and create tools you didn't think you could. Get 'the SPARK' newsletter every Thursday + tutorials and guides in between

Kim reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

The bulk of my professional background was in retail management — training manager, then district manager. All of that changed when I was widowed in 2003. I was 32. My kids were six and two.

Even before that, I’d always had an entrepreneurial itch. I opened a retail scrapbook store with a friend in 1998, did some contract recruiting — there was always this sense that I was meant to be doing something else, I just hadn’t found it yet.

Five years after losing my husband, I had a small financial cushion and attended a conference in San Francisco called the Wealth Expo. A friend and I stumbled into a breakout session on internet marketing. That was 2006, and I was hooked.

I didn’t jump right away, but by 2008, I made the decision to go all in — build a business from home so I could be there for my kids. I was completely non-technical. That didn’t stop me.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

The moment wasn’t one single thing — it unfolded over a few years. But losing my husband made it crystal clear: there was no way I could be a retail district manager and actually be present for my kids. The job is too demanding, too consuming.

What gave me the runway to act was a small settlement after his death. Nothing to retire on, but enough to buy me some time. And I’d always wanted to work for myself anyway — this just made the decision undeniable.

Right out of the gate I did two things: hired a coach (mostly learned what not to do) and enrolled in a social media marketing course when social media was barely a thing. I showed up, connected with people, did the work.

When I say I wasn’t technical — I mean it. But I was committed. I showed up every day, and that was enough to keep moving forward.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

One of the major retailers I worked for in San Francisco had me opening new stores constantly as a district manager. That process — the coordination, the planning, the structure, the scheduling — it’s actually not that different from launching anything online. You’re moving a lot of pieces at once and someone has to hold it all together.

I was in management very young, so I learned early that hard work isn’t optional and things just have to get done. That mindset carried over completely.

And retail is people. Customers, employees, conflict, communication — all of it. Learning to read a room, build trust quickly, handle difficult situations... that translated more than I ever expected into building an audience and working with clients.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

In 2008, I jumped on every platform that existed. Facebook, Twitter, all of it. I just showed up and did what I was supposed to do. Some of those accounts are long gone now, but I was everywhere early.

I also knew from the start that writing and SEO mattered, and that’s when I fell in love with WordPress. I grabbed the domain “The WordPress Chick,” became the WP Chick, and just shared my journey. I kind of fell into that space — and it worked.

But honestly? My podcast was probably the single biggest factor in growing my brand. What started as the WP Chick podcast eventually became the Kim Doyal Show, and I did it for almost ten years. I alternated solo episodes with interviews — that rhythm was intentional. The interviews built my network and some of my best friendships. The solo shows built trust.

Hour-long episodes do something interesting — people spend real time with you. They get to know how you think, how you work, what you actually believe. I became a trusted voice, almost like a friend. Someone once tweeted that I seemed like I’d be fun to have a beer with. I responded that yes, I absolutely was.

The podcast made me relatable in a way no other platform could.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My work is for the person who doesn’t think they’re technical enough — but has a lifetime of wisdom, experience, and skills they haven’t fully monetized yet. Specifically, I’m talking to midlife women entrepreneurs who want time freedom and financial growth, and who are looking at AI thinking... where do I even start?

I used to say, when I was figuring out WordPress: “If I can build IKEA furniture, I can figure this out.” I was never a coder, never a developer. I’m still not. But I learned enough to build, to teach, and to solve real problems — and that’s exactly the bridge I help others cross now.

Because here’s what I see: there are a lot of people 45 and older who know AI is important, who don’t want to be left behind, but who have no idea how to integrate it into their actual business. They’re not intimidated by work — they’re intimidated by tech. Those are two very different things.

My sweet spot is showing people they can build what they need. Custom solutions, content systems, operations tools — things that used to require a developer. The era of “I’m not technical enough” is over. You just need someone to show you how. And yes, people are already paying me for it.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

Honestly? More has been easier than I expected than hard. I’ve been working online long enough that I’m constantly blown away at what’s possible — and I just keep applying the same principle: if I can build IKEA furniture, I can figure this out.

The hardest part has been carving out my own space. There’s so much happening in AI right now, and a lot of noise around it. I’m not interested in building some enterprise software company — that’s not where I am in my life, and it’s not what lights me up. But I do want to scale financially, serve my audience well, and maintain the quality of life I’ve built. That combination means the path has been slower, and I’m genuinely okay with that.

I’m still finding my spot. It’s going to be a combination of everything I bring — the experience, the voice, the technical skills I’m building in real time. It’s evolving every day, and honestly, that’s the part I love most.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

The Substack journey felt a little bumpy at first — mostly because I was still carrying old habits into a new platform. My newsletter had been a structured weekly format with segments for five and a half years, and that worked really well. But when I actually looked at my Substack data, the individual standalone posts were outperforming the newsletter by a wide margin. That was a turning point.

The best advice I can give? Tune out the noise and just start. Clarity comes through doing, not planning. You have to show up, write, engage, connect — and then let the data tell you what’s working.

There are a lot of formulas floating around for growing on Substack, but honestly the thing that matters most is being a genuine person who’s interested in other people. I’ve had handfuls of “let’s just hop on Zoom and meet” conversations, and they’ve turned into real friendships. It feels like early Facebook did — 2008 to maybe 2015 — when people were actually there to connect.

On consistency: it doesn’t look the same for everyone, and that’s fine. Don’t adopt someone else’s cadence if it doesn’t fit your life. The more you publish, the clearer everything gets — what you want to say, who you’re saying it to, and what actually resonates.

“What nearly made you quit, and what actually kept you going?”

Plenty of times. I’m 18 years into this as of this year, and there have been a lot of rough patches along the way.

The through-line on most of them? Not trusting myself. Every single time I ignored a gut feeling about working with someone or taking on a project, it went sideways. Without exception. The internet marketing space is where influencers were born, and there is so much noise and so much bullshit wrapped in a very convincing package. I’ve invested a lot into masterminds, coaching, and programs over the years — some of it transformative, some of it a very expensive lesson in discernment.

What kept me going was usually something small. A win. A moment of realizing I was actually there for my kids, or later for my parents, or just... watching my siblings come home from traditional jobs completely drained, their schedules not their own. That was enough to recalibrate.

I’ve had significant launches — the Content Planner did really well and showed me what’s possible. I’ve also had months where I was barely scraping by. Both are real. But honestly? The worst day working for myself is still better than a great day at a job.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

The most honest advice I can give is also the least sexy: be patient and do the work. It doesn’t happen overnight, regardless of what you’ll hear out there.

And it depends where you are in your life. Hustle culture used to genuinely make me angry — I was a single parent, raising two kids alone, running a business. I couldn’t have worked harder if I’d tried. The “if you wanted it badly enough you’d grind more” noise was not just unhelpful, it was insulting. So go at a pace that actually works for your life, but be consistent. Those are not the same thing.

Trust yourself. If something doesn’t feel right, listen to that. You will save yourself time, money, and a lot of heartache.

Get comfortable with discomfort — because you’re going to have to stretch in ways you didn’t anticipate. Most people don’t love selling, and they especially don’t love selling themselves. I still wrestle with it. But if you want to monetize your skills, build a real business, keep the lights on... you have to learn to sell. Not manipulate, not perform — sell. And that starts with understanding your own why deeply enough that sharing it stops feeling like a pitch and starts feeling like a conversation.

Bad days are part of it. They don’t mean you’re failing. They mean you’re building something real.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

Everything has been an evolution, and it’s all been connected. Web design agency, outsourcing company, podcasting, done-for-you services, coaching, content and copy and email marketing. I’ve taught courses, built curriculums, and launched an e-commerce product — the Content Creators Planner — that we scaled to half a million in sales. I studied copywriting, went deep on every skill I picked up, and somewhere along the way realized that all of it was preparing me for exactly this moment.

So right now, everything runs through Kim Doyal. Client work, teaching, content. I recently relaunched my YouTube channel and I’m tightening the focus so it’s entirely AI-based and built around serving my ideal audience. The throughline across everything is the same person, the same voice, the same mission.

I’m also working on something I’ve been calling a secret project — a platform specifically for women, completely outside the marketing space. There’s a digital app component, content, and something designed to genuinely help women in a different way. The website is built, I’m developing the content, and I’m giving myself a full year to do it right. Once the app is running, the goal is to grow it, scale it, and eventually — maybe — sell it.

I have no interest in rushing it. I’ve learned enough to know that the best things I’ve built were built with intention.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

The decision that changed everything was choosing to start an online business when I had no technical background whatsoever. I just had faith in myself and a commitment to a different kind of life.

Freedom was the driving force for so long. I’d worked for big corporations, six days a week, salaried, with the kind of expectations that grind you down slowly. The first Christmas I worked for myself felt almost foreign — the chaos of retail’s fourth quarter just... wasn’t there. That quiet was everything.

As for what’s next: I want to scale, but on my own terms. I have what I’m calling a boutique agency, continuing to work with women and help them integrate AI into their businesses in real, meaningful ways. I’m diving head-first into agents and automations, testing what I’m learning across different spaces outside of marketing. The secret project. YouTube. All of it.

I don’t have a burning desire to be a household name or build an enterprise company. Genuinely couldn’t care less about that. I want to do work I love, spend time with people I care about, and travel. Life is really good.

Nobody knows where AI is heading — and honestly, that’s part of the magic. Right now this is a “let’s see where it takes us” chapter, and I keep surprising myself with what’s possible. I’m having a ball.

Links & Resources

Connect with Kim…

On YouTube

On LinkedIn

Website: kimdoyal.com

Kim Doyal

Build AI-powered solutions without a coding degree. After 17+ years online, I'm showing you how to use AI to save time, scale smarter, and create tools you didn't think you could. Get 'the SPARK' newsletter every Thursday + tutorials and guides in between

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Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

Andi had what most people aim for… experience, clients, and a stable freelance business.

On paper, everything made sense. In practice, she felt stuck.

She wanted to do more than client work and local projects. She wanted to reach a wider audience and be part of a bigger conversation.

So she started creating in English and shifted her focus to building online.

No built-in advantage. No quick results.

Instead, she focused on writing consistently, testing ideas in public, paying attention to what people responded to, and maximizing early traction.

Ditch the Templates came from that transition. A place to think in public, test ideas, and build something that didn’t depend on clients alone.

In this Playbook, Andi breaks down what it actually took to start again, what most people get wrong about Substack, and how she turned her writing into a successful business.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Andi

Andi Bitay is a content strategist and Substack mentor.

She helps creators and entrepreneurs build on Substack, grow their audience, and turn their writing into paid offers.

Her work focuses on clear thinking, strong positioning, and creating content that connects and converts.

You can follow her work here →

Ditch The Templates • Andi Bitay

The creator career is real. Strategy, trends, and honest talk for those building one.

Andi reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I always knew I wanted to work in communications. I started out as a TV editor, but the world was shifting quickly, and somehow, I managed to move with it. I became one of the first online journalists, bloggers, and social media managers in my home country. I fell in love with digital content early on. It didn’t matter if it was my own or a client’s, I just loved creating.

The hardest part of my career was the time I spent at agencies. On paper, everything looked right. I was moving forward, climbing the ladder, but I was deeply unhappy. I couldn’t really find myself in that environment.

So when my son was born about 10 years ago, I went freelance and never looked back. Freelancing gave me freedom, but over time, constant client work started to drain my creative energy. That’s when I launched my own lifestyle blog, and later built a business helping female entrepreneurs with their social media.

Still, something was missing. The really exciting things just weren’t happening there. In Eastern Europe, trends tend to arrive a few years later, and I could feel that gap more and more. I started craving something bigger: working internationally, being part of the global conversation, earning more, and staying in sync with what’s actually happening online.

So I began creating content in English. It wasn’t a straight path, but eventually, it led me to Substack.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

Honestly, it was a quiet inner voice that kept coming back to me. It said: if you don’t even try, you’re going to regret it. And at some point, staying where I was—doing what felt familiar and safe—started to feel worse than the idea of trying and failing.

One of the biggest challenges was my English. I hadn’t really used it since my school years. I’d never worked in English before; at most, I’d ordered food on holidays. That slowed me down a lot and brought up a fair amount of frustration.

There was also a harder realization: the results I had achieved in a small country didn’t really carry weight internationally. It felt like I had to start all over again from zero.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

Over time, I realized that people aren’t really interested in how convincingly I can prove I have a decade of experience. That’s not what builds trust. What actually matters is something much simpler… and much harder. Showing how I see things, sharing my perspective, and saying what I really think.

And I recognized something familiar in that. It’s the same thing I had already learned back home, just on a smaller scale. The moment I stopped trying to “prove” myself and started showing my way of thinking—how I connect the dots, how I see the bigger picture—people began to listen. They started to trust my voice.

I wouldn’t even call this a skill, it’s more of a mindset. But having experienced this once before was a huge advantage. I could go back to that place within myself and rebuild from there. Of course, it also helped that I adapt quickly to new things. I can usually figure out how a platform works quite fast, and I’m genuinely curious about how people use it.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

That’s a good question. For me, it really comes down to whether I actually enjoy being on a platform. I need to feel excited to open it every day. When that feeling fades, I slowly disappear from there. That’s exactly what happened with Instagram and LinkedIn.

I first started writing on Medium, and that’s where I came across Substack. I gave it a try, and something just clicked. It felt much more motivating, almost like going back to my early blogging days.

Right now, Substack is my main focus. It’s where I build visibility and credibility, and it plays a central role in both my work and income. At the same time, I do want to slowly expand to other platforms like Instagram and Pinterest. But I’m careful with that because I don’t want to burn myself out, so I’m taking it step by step rather than trying to be everywhere at once.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My clients often tell me that I help them see things differently, and I point out things they couldn’t see before. In a way, I help them rewire how they think about their content and give them a completely new perspective.

I mostly work with female entrepreneurs, writers, and experts who want to build a home base for their content on Substack. I help them reach more people, monetize their work, express themselves more clearly, and create real connections with others.

Because communication is complex. It’s not just strategy and numbers, it’s emotions first. What your audience feels matters, but just as much, what you feel as a creator matters too. The real work is bringing those two into alignment so that the content resonates, the connection is real, and the business is still sustainable and profitable. That challenge is what motivates me every single day.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

When I started writing in English, I thought it would be much easier. I assumed I could more or less translate what I had already created before, and that people would quickly come and want to work with me. To be honest, I was used to things working that way. But it didn’t happen like that.

It took me almost two years to reach my first meaningful business breakthrough. There were many moments when I wanted to quit. But by then, I had already invested so much time and energy that turning back didn’t feel like an option anymore. For the first time, I felt like I was truly fighting for something that didn’t come naturally or easily into my life.

I was facing myself on a deeper level. My self-worth, my mindset. Constantly questioning what I might be missing, what I couldn’t see about my own patterns that was holding me back. And at the same time, I had to keep my local business alive. I couldn’t just walk away from my existing income. So I was building two things in parallel, and that was exhausting.

What turned out to be easier, though, was the connection itself. Once my message started to land, once I found my voice in English, the right people did find me. And those connections felt even deeper and more aligned than I had expected.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

I think this journey looks very different for everyone. People come to Substack with different goals, styles, and backgrounds… But one thing I see over and over again is this: people don’t really dare to step outside the clichés. They hold back from sharing sharper, more honest, sometimes uncomfortable thoughts.

Instead, many try to prove how knowledgeable and smart they are, and how worthy they are of a subscription. It almost feels like they’re trying to write as if they were featured columnists at a major publication. And that’s exactly where the connection gets lost because the audience doesn’t see the person behind the words. The writing doesn’t stay with them. It’s not memorable. Trust doesn’t have a chance to build.

At the core, we’re drawn to something much more human: stories, perspective, personality. These are ancient forces. We gather around people who make us feel something or make us think differently. If a piece stays with you hours or even days later, that’s when it truly lands. But if someone just hits “like” and forgets it a minute later, then it didn’t really reach them.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

It’s worth it. And if you stay aware, keep shaping things as you go, and don’t let the fear of failure stop you, you’ll get where you want to go. What really matters today is flexibility. Not just financially, but in how you think. The ability to adapt, to shift, to let go of what no longer works. We don’t just not know what the world will look like in 10 years; we don’t even know what it will look like by the end of this year. That uncertainty isn’t temporary anymore, it’s the new normal. And the more you can build your work and your mindset around that, the more freedom you’ll actually have.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

Right now, in terms of platforms, my main focus is Substack, but I’m planning to gradually expand beyond it. In the background, I offer Substack strategy and management, LinkedIn ghostwriting, and social media management. These provide consistent income and keep everything grounded.

One of my most popular services is the Substack Audit. And then there’s Bloom Your Substack, a 4-week 1:1 program I’ve now launched twice, and both times it sold out within 24 hours. This spring, I’m also planning to introduce smaller digital products, along with a mini course designed to help beginners get started on Substack.

So it’s a mix: client work for stability, and my own offers for growth and scalability. Over time, these pieces are starting to support each other more and more.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

Looking back, the decision that changed everything was definitely the moment I hit ‘publish’ on my very first imperfect English post. Right now, I’m all about growing Ditch the Templates and evolving my services.

At the same time, I’ve just launched a second Substack called Still Becoming. It’s a bit of a passion project, less about business and more about community and personal fulfillment. I have big plans for it.

Links & Resources

Connect with Andi on her two publications→

Still Becoming

Stories, spaces, and the things that shape how women over 40 build a life that's theirs.

By Andi Bitay

Ditch The Templates • Andi Bitay

The creator career is real. Strategy, trends, and honest talk for those building one.

Related Articles

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The “general post” era is over

Read More

Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

Farida started in international finance and global affairs, working across NGO and multilateral projects where her job was to make complex decisions clear and usable.

Her career moved through project-based roles across different settings. That gave her a front-row view of how decisions are made, what drives them, and what rarely gets explained.

Over time, she noticed a pattern. Work often ended for reasons other than the problem itself.

When Covid hit, that reality became harder to ignore.

Instead of relying on one path, she started building others in parallel, expanding her work and testing new directions.

Lights On came out of that shift. A place to write, think clearly, and explain what is often missed.

In this Playbook, Farida shares how she approached that transition, what shaped her thinking, and how she is building work that does not rely on a single path.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Farida

Farida Khalaf is the writer behind Lights On, a Substack that examines systems, decisions, and real-world dynamics with clear, evidence-based thinking.

Economist. Data engineer. Writer. In that order, and sometimes all at once.

With experience across NGOs, multilateral programs, and government work, she draws on business analysis, data, and cybersecurity to make complex information clear and usable.

That clarity carries into her writing, for readers who want to understand what is actually happening, not just being told what to think about it.

You can follow her work here →

Lights On by Farida

A systems-driven newsletter from a data engineer and cybersecurity thinker, decoding complex data, technology, and business trends into actionable insight.

By Farida Khalaf

Farida reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I am an economist by degree and a data engineer by everything that came after.

My first job was account settlement grant projects between countries, calculating liabilities, tracking accountability across every task. The reporting was the core of it. Not just visuals, but explanation. Why did this number move? What does this pattern mean legally, contractually, in the real context of two governments trying to work together? I had to make complexity legible to people who didn’t have time for the full picture.

That became my strength and it still is. I don’t just analyse data. I tell its story.

Most of my career has been project-based, joined through word of mouth rather than HR pipelines. Each project lasted six months to three years, with its own terrain and its own problems. But underneath all of it, the dynamics of data are universal. The context changes. The logic doesn’t. Two master’s degrees, international finance and global affairs gave me fluency in the NGO and multilateral world. World Bank, UN programs, governmental initiatives.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

Working in NGOs taught me something nobody tells you: the work doesn’t always stop because the problem is solved. It stops because of politics. Programs that were genuinely needed get cancelled not for lack of initiative or funding, but because of the push and pull between decisive players who are thinking about the relationship, not the problem.

When COVID hit, the shutdown wasn’t a prediction anymore. It was a process. I watched the entire project-based workforce reckon with what I had always known privately: nothing is permanent.

I had a parallel passion for cybersecurity. I started doing penetration testing, some bounty hunting. That opened consulting doors in data security and cloud management. Contract-based, word of mouth but it removed the anxiety of a single point of failure and opened the door for a learning curve.

The pivot wasn’t one moment. It was the accumulation of evidence that agility was a feature, not a bug.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

Reporting. Knowing who I am writing for before I write a single word.

A brief for a minister reads differently from a technical report for an engineering team. I spent years finding the right frame, the right level of detail, the right language for the right audience. That transferred directly into newsletter writing except now my audience is global, curious, and doesn’t owe me their attention.

Data also trained me to think in evidence. I don’t like arguments that float. I want the number, the mechanism, the case that explains why something is true. That discipline makes my writing explainable, not commentary.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I tried Medium and LinkedIn. Neither gave me traction — their algorithms work for the platform, not the writer. A friend, Devansh, told me to try Substack. I noticed the difference immediately.

Writing is not my primary income yet I still consult and take NGO contracts. But the newsletter is building something consulting alone cannot: a body of work that exists independently of any single client.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

I have been posting two to three times a week for a year. The first three to six months, it was mostly me and my friends reading. That is the honest truth and people need to hear it more.

Traction comes slowly. Consistency is the only strategy that actually works. For consistency done right, watch Dr. Sam Illingworth. For understanding Substack’s visibility mechanics, Jenny Oyung’s recent post on substack visibility analysis is excellent.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My newsletter is called Lights On. It exists for people who want to understand what is actually happening not the hype, not the marketing narrative. I try not to deliver a message. I try to explain the message that is already there, waiting to be seen clearly.

We live in a mimicry society. Most of what passes for analysis is just a louder version of the consensus. I want to offer the clarity that is apparent but overlooked.

“What nearly made you quit, and what actually kept you going?”

The invisibility of the early months is real. Writing carefully about things that matter to you and hearing almost nothing back requires a specific stubbornness.

What kept me going was the work itself. Each article made the next one sharper. The pivot is a feature, not a bug, I have spent my career on timed contracts with no permanent attachment. That trained me for this.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Be genuine. Be part of someone else’s growth sincerely not strategically. If you can lift an article or share a newsletter, do it because it deserves to be seen. Community built on reciprocal generosity is the only kind that lasts.

And be patient. Consistency is not glamorous advice. But it is the only one that is actually true.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

That originality matters. In an AI world flooded with slop writing, the articles that circulate do so because of the quality of their thinking not because of ads or optimized keywords.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

I decided early to write what I actually think, in the register I actually use, about things I have genuinely studied. That decision I would make again without hesitation.

What’s next: more collaborations, expanding Lights On into new territories, and eventually making the writing the centre rather than the complement.

Links & Resources

Connect with Farida→

Lights On by Farida

A systems-driven newsletter from a data engineer and cybersecurity thinker, decoding complex data, technology, and business trends into actionable insight.

By Farida Khalaf

Favourite recent articles

Si-morgh Is Me and You

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Read More

Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

Revenue does not come from more content. It comes from conversion.

She did not leave because she lacked success. She had a high-flying corporate career. On paper, everything worked. The roles. The travel. The reputation.

Then burnout forced a decision…

Keep building a career that paid well but felt empty. Or build something she owned.

What she did next is the playbook.

Inside, Ana breaks down how she went from writing for free to building a system that turns readers into paying customers. She explains why most newsletters fail to make money, even with good content, and what to fix first.

She is clear on pricing, selling, and why even if your newsletter has a small, committed audience, it can outperform a large passive one.

She also shares what nearly made her stop, what changed everything, and how she built systems that keep working without her being online.

If your content is good but your income does not reflect it, this one is for you.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Ana

Ana Calin is a Forbes-recognised marketing leader, mama to Eva, and the creator of How We Grow — one of the fastest-growing newsletters on Substack with 70,000+ subscribers.

She went from corporate marketing director to $119K/month in 14 months, hit Bestseller in under 3 months, and built the whole thing while pregnant.

She teaches newsletter creators how to build something that pays them — without a massive audience, sales calls, or burnout.

You can follow her work here →

How We Grow

Join 70,000+ creators who are growing businesses, not just audiences. Every week I help creators turn "I don't know what to sell" into a clear offer people love to buy.

By Ana Calin

Ana reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

15 years in corporate marketing. Amsterdam, San Francisco, London. 120+ countries. The kind of LinkedIn profile that made people say “wow.”

And I was miserable.

Not in a dramatic way. In the slow, quiet way where you stop noticing you’re unhappy because you’ve been unhappy so long it just feels like Tuesday.

I quit at 35. No plan. No audience. No newsletter. Just a very clear feeling that I was building someone else’s thing — and the equally clear feeling that I had about 40 more years of working life left, and I refused to spend them making someone else rich.

I started multiple businesses. Some worked. Most didn’t. Then in September 2024, I launched a Substack called How We Grow. 10 subscribers. My husband, two friends, and some LinkedIn connections being polite.

14 months later: 70,000+ subscribers. $119K+ months. Bestseller in under 3 months. Forbes called it a “must-subscribe-to.” I built the whole thing while pregnant — and then while breastfeeding at 3am with my daughter Eva on my chest.

The path wasn’t a pivot. It was an escape.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

Must be when I fainted in a hotel bathroom. In Singapore. After travelling to three different continents within the same week.

Not dramatically. Not in a way that made a good story at dinner. I was on a work trip — another city, another conference, another morning of smiling at people whose names I’d forget by Thursday. I got up, walked to the bathroom, and the next thing I knew I was on the floor looking at the ceiling tiles.

My body quit before my brain had the courage to.

That’s the part nobody tells you about burnout. It doesn’t announce itself. It doesn’t give you a dramatic exit moment. It just pulls the plug while you’re brushing your teeth in a hotel you don’t want to be in, in a city you flew to for a meeting that could’ve been an email.

I lay on that bathroom floor and had the clearest thought I’d had in years: This is not the life I’m supposed to be living.

Not “this is hard.” Not “I need a vacation.” This is not it.

What did I push through to act on it? Everyone. My family thought I was having a breakdown. My colleagues thought I was ungrateful. My bank account thought I was insane.

The average woman waits 2.3 years longer than the average man to start a business — not because of capability, but because of how many people tell her to “be realistic.”

I stopped being realistic. Best decision I ever made.

And I haven’t been back on that bathroom floor since.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

The biggest one nobody expects: corporate presentations.

I spent 15 years making PowerPoints nobody wanted to watch. Turns out, structuring a boring 40-slide deck for a VP who doesn’t care teaches you something invaluable: how to hold attention when someone doesn’t owe you any.

That’s the entire game on Substack. Your reader owes you nothing. They will close your email in 3 seconds if you don’t earn the next sentence. Corporate taught me how to survive in rooms full of people who didn’t care — and that’s exactly what the internet is.

The second one: brand positioning. In corporate, I positioned products worth millions. Now I position newsletters. The frameworks are identical. The product just happens to be me.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I chose Substack because I was done being a renter on someone else’s platform.

On Instagram, the algorithm owns your audience. On LinkedIn, one policy change can wipe your reach overnight. On Substack, every subscriber is an email address I own. Nobody can take that away. No algorithm change, no platform pivot, no CEO having a weird Tuesday.

Substack is my home base. My revenue engine. My community. My content lives there. My paid subscribers live there. My courses, my workshops, my digital products — everything funnels back to Substack.

Notes are my storefronts. They bring new people in. But Substack is the house they walk into. I’ll never build on rented land again.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My work is for the woman with 200-2,000 subscribers who knows her content is good but can’t figure out why nobody’s paying for it.

She’s not struggling with writing. She’s struggling with conversion. She has a content strategy but no monetization strategy. And she’s been told she needs 10,000 subscribers before she can make money — which is the single most expensive lie in the creator economy.

I don’t teach people to write better. I teach them to convert the readers they already have. That’s the gap. That’s what people pay for.

“What turned out to be harder than you expected when you started… and what was easier than you imagined?”

Harder: Selling without feeling gross. I’d spent 15 years selling other people’s products with zero emotional attachment. Selling MY thing? Terrifying. Every email felt like handing someone a piece of my diary and saying “is this worth $7?”

It took me months to realise: selling isn’t asking for money. It’s telling people the door is open. If you believe what’s on the other side is genuinely valuable, selling is a service. If you don’t — that’s not a sales problem. That’s a product problem.

Easier: Getting subscribers. I thought I’d need to grind for years. Substack Notes changed everything. I posted consistently — personal stories, specific numbers, contrarian takes — and the platform’s algorithm did the heavy lifting. 60-70% of my subscriber growth came from Notes. The platform WANTS you to grow. That was a shock coming from Instagram, where the algorithm seemed to personally dislike me.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

The journey has been the most fun I’ve had working in my entire career. And I’ve worked in some glamorous places.

My advice is controversial, so here it is:

1. Clean your list before you grow it. I delete subscribers every month - ghosts who’d never opened a single email. My revenue went UP. Everyone obsesses over growing the number. Nobody talks about the fact that a dirty list is actively hiding you from the people who love your work.

2. Stop writing. Start converting. Your writing is already good enough. If people are subscribing for free, your content isn’t the problem. Your conversion system is. Set up a welcome email. Build an upgrade sequence. Write a paywall paragraph that actually sells. These things take an afternoon and work forever.

3. Post Notes like your business depends on it. Because it does. 3-5 Notes per day. Personal stories with data. Contrarian takes. Permission slips. My most viral Note wasn’t about Substack at all — it was about the average age women pivot careers. It got thousands of likes because it spoke to identity, not strategy.

4. Charge more than you think you should. I charge $97/month. Everyone said I was crazy. My subscribers stay longer than anyone else’s. A $5/month subscriber is a tourist. An annual subscriber at $177 is a resident. Build for residents.

5. Make it about them, not your content. Your paid tier should feel like joining something — not reading more posts. Monthly challenges, live access, surprise bonuses, anniversary touches. People don’t cancel things they belong to.

“What nearly made you quit, and what actually kept you going?”

Eva was 11 days old. It was 3am. She was screaming. I was crying. My shirt had milk on it for the third day. And I was convinced I had to choose — the baby or the business.

Then my phone buzzed. Stripe notification. $97. Then another at 4:12am. Another at 6:30.

I hadn’t sent an email. Hadn’t posted. Hadn’t touched my laptop in days.

The systems I’d built kept running while I was falling apart in the dark.

That night nearly broke me. And it’s also the night that proved the whole model works.

What kept me going? Not discipline. Not hustle. Systems. I built a business that doesn’t need me to be present — it needs me to have BEEN present. Past tense. That’s the difference between a job and a business.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Stop asking for permission.

I mean it literally. Stop polling your friends. Stop asking your partner if they think it’s a good idea. Stop reading one more article about “the right time to start.”

The average woman pivots careers at 39. The average new female entrepreneur is 42. The average first-time female millionaire is 49.

You’re not behind. You’re not too late. And you definitely don’t need anyone’s approval.

Start with one thing: publish something. A Substack. A post. One piece of writing that says “this is what I know and this is who it’s for.”

It doesn’t have to be perfect. My first post was embarrassing. My 50th was great. My 200th made me $119K in a month. But the 200th only exists because the embarrassing first one did.

Momentum creates clarity. Not the other way around.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

I currently have 5 revenue streams and they all funnel through one place: my Substack.

1. Paid subscriptions. The foundation. Recurring revenue.

2. Digital products. Workshops, ai tools, and other resources. These serve as entry points — people buy a product, discover the newsletter, and become paid subscribers.

3. The 10K Launch Lab. My flagship cohort programme. 30 days. One task per day. Students build and launch their first offer. Average first-launch revenue: $3,847.

4. Brand partnerships and sponsorships. Selected carefully. I only work with brands my audience actually needs.

5. Affiliate income and Substack recommendations. Passive. The recommendation system alone delivers thousands of subscribers on autopilot.

The flywheel: free content on Notes and sometimes LinkedIn brings people in → they subscribe to How We Grow → the welcome email converts some to paid → paid subscribers become the warmest audience for launches → launches fund the business → the business funds my time to create more free content.

It’s a loop. It runs while I sleep. That’s the whole architecture.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

The decision: Quitting the corner office at 35 without a plan.

Everyone called it reckless. In hindsight, it was the most calculated risk I’ve ever taken. Not because I knew it would work — I didn’t. But because I calculated the alternative: 30 more years in a career that made me feel nothing. That math was scarier than any startup risk.

What’s next: Two new publications. “How We Buy” — about buyer psychology, the science of why people pay, rooted in behavioural economics. And “Wear Orange” — something deeply personal about fertility, motherhood, and the journey that brought Eva into my life.

I’m also scaling the education side. More workshops. More cohorts. More ways to take the system that built my $100K months and put it in other people’s hands.

The vision is simple: build something that pays you without consuming you. That was always the mission. It hasn’t changed. The scale has.

Links & Resources

Connect with Ana…

→ 10K Launch Lab

→ Start Here

→ LinkedIn

→ Free AI Offer Flow Tool

How We Grow

Join 70,000+ creators who are growing businesses, not just audiences. Every week I help creators turn "I don't know what to sell" into a clear offer people love to buy.

By Ana Calin

Related Articles

I tracked every dollar my newsletter made for 12 months

I charge 20x more than most Substacks. Here's why my subscribers stay longer

Why the Most Profitable Substack Creators in 2026 Will Be Storytellers, Not Strategists

Start Here: The $50K/Month Newsletter Nobody Saw Coming

On Forbes: How Brands Can Win On Social Media In 2025: Nine Trends To Watch

Read More

Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

Daria didn’t come from a technical background. She built her career by moving across roles, learning fast, taking on whatever needed to be built next and never staying in one lane.

Then AI started changing what one person could do.

She began testing tools and sharing what she found… at first, it was just another experiment, but it quickly didn’t stay that way.

Inside this interview, Daria talks about the moment things started to click, what she noticed early that others missed, and how her background started to work in her favour.

She gets into the reality of building with AI as a non-technical founder, what actually moved the needle early on, and exactly how she grew her Substack into a compounding audience and income stream.

If you are trying to work out how to stay relevant as AI moves fast, this one will inspire.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Daria

Daria is the writer behind AI Blew My Mind, a newsletter about using AI in real work without a technical background.

Her career spans marketing, consulting, sales, project management, and education. She is an AI founder who delivers practical tools and use cases through a non-technical lens.

Today, she shares clear, practical breakdowns that help experienced professionals use AI in their own work and rethink what they can build on their own.

You can follow her work here →

AI blew my mind

Turn your decades of experience into AI systems that work 24/7 so you don’t have to. Every week, I help you rethink how you operate and build workflows that run for you. (So good, readers say they cancel their day when a new issue drops.)

By Daria Cupareanu

Daria reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I’ve never had a linear career. I started with marketing roles, then an advisory role at PwC, then B2B sales, then project management. From there I landed in education, designing non-formal programs for teenagers, students, and professors across Romania, everything from Python and SQL to critical thinking and decision-making. That’s where I first discovered my passion for education.

Then I joined a food delivery platform, where I built an account management department for long-tail partners from scratch. Just me at first, grew it to ten people. We put Romania on the global map for commercial results. But even there, I was never doing one thing. Email marketing for 5,000+ partners, team building, business and commercial strategy, data analysis, training programs. Always wearing every hat in the room.

While still at that company, I started my own startup: an educational app for soft skills that later evolved into a recruitment tool. That led me deeper into AI, where I started building tools as a non-technical person, and that was the real mind-blowing moment in my journey.

One night, my business partner said: ‘You’re already sharing all these tools and experiments with me anyway. Why not share them publicly?’ The next day I created my Substack and published my first article.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

There was no big moment. I was already on a path of building businesses and trying different things. My strategy was simple: experiment as much as possible, see what works, double down. What AI changed was that I could finally build things on my own that before would have required an entire team. That opened up everything. The newsletter was one more experiment in the mix. It just happened to be the one that took off.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

Being a generalist. For a long time I thought that was a weakness. In my early career, I kept jumping between roles while my peers were years deep in the same position, getting promoted, earning more. I was always starting from scratch with overlapping skills but never the “proper” experience companies pay you more for. That was frustrating.

But everything I collected along the way compounded. Finance and negotiation from my early roles. Building processes from scratch for an entire department, scaling a team, and working heavily with data. Curriculum design and teaching from my years in education. And then marketing, partnerships, product development, and user psychology from running my own startup.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I chose Substack because I was already subscribed to newsletters I admired here. That was the whole decision-making process. I only learned about alternatives after joining. Turns out it was a great choice anyway, due to the built-in community features, since I had no existing audience to pull from.

Almost a year in, Substack generates a meaningful part of my income through paid subscriptions, but the value goes beyond that. Having an audience means I can build and sell products, and consulting clients find me through my writing.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

I struggled to find my niche for months, being a generalist makes that hard. But as the newsletter grew and paid subscribers started coming in, I began analyzing who they were, and a clear picture emerged. My audience is mostly seasoned professionals, 50 and older, with decades of experience in their fields. CEOs, business owners, consultants. People who are incredibly good at what they do and want to either reinvent themselves with AI or start adopting it in their businesses to gain leverage and scale.

What I think I do well is give the full recipe. My content is always practical and I don’t keep anything to myself. When I discover something that works, you get the whole breakdown so you can take it, apply it to your own work, and experiment with the results yourself. People have also told me I have a way of explaining complex, technical things so they feel approachable and clear.

Plus, I want every piece I publish to make you think: I had no idea AI could do that for me. That’s the idea behind AI blew my mind.

“What turned out to be harder than you expected when you started… and what was easier than you imagined?”

When I started, I thought I’d write quick, short articles. Here’s a tool, here’s what I did with it, done. But as I evolved, I realized I love deep dives. I want to approach a topic end to end and not leave anyone wondering halfway through, thinking ‘I should google that’. So my quick posts turned into comprehensive guides with practical walkthroughs, research, and my own takes. The time it all takes caught me off guard, and not just the writing itself, but everything around it: engaging with others, building community, being present. I love that part, but it adds up fast.

What was easier than I expected was growing an audience. Within the first few days I had subscribers from markets completely different from my network in Romania. I kept comparing it to getting users for my startup, which had taken so much longer. Of course, there are others here who are growing much faster than I am, but when I look at where I am today versus where I was yesterday, I’m really happy with it. Especially because it happened organically, without external channels or paid marketing pushing it along. I just didn’t expect that.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

This journey changed my life in ways I didn’t anticipate. Having an audience is the start of so many things, from launching products to building a community to creating a world around what you love doing.

My advice: don’t overthink it and don’t get stuck in your head before you’ve even started. Just experiment. Then watch the data, pay attention to what drives engagement and growth, and double down on those things. Listen to your readers too. A lot of my best content started as a reader request, and combining what your audience tells you with what the data shows will take you further than any growth hack. Keep an eye on what peers are doing to learn from them, but always test things for yourself, because there’s no single recipe that works for everyone. You build your own path.

Lastly, you do have to enjoy the process. It requires serious commitment, and if it doesn’t energize you, it’s going to be hard to sustain.

“What nearly made you quit, and what actually kept you going?”

I never wanted to quit. The only struggle has been the math. For a long time, and honestly still now, the effort I put in far exceeds what I get out of it financially. If I were paid hourly for all the time I invest in Substack, I’d be making a lot more money elsewhere. That gap can be a struggle at times, because you don’t grow overnight. It happens day by day, with better stretches and harder stretches, just like everything in life. But I see this as a long-term game and I’m at peace with that.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Don’t pivot by burning everything down. Run things in parallel, experiment on the side, and let the results guide you. Give things time, do the marketing even when you’d rather skip it, and put yourself out there. It will help you in ways you can’t predict.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

Everything feeds into everything else. The newsletter attracts readers. Some become paid subscribers or consulting clients. The consulting gives me real-world experience that makes the content better. Add products I build on the side, and it’s one ecosystem where each piece strengthens the others.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

The decision that changed everything was accepting who I am. I’m different from my peers. I don’t have the same goals. Once I realized how deeply I value freedom and independence, I fully embraced it, even when it meant taking the harder path, earning less for a while, and starting over. That bet on myself changed everything.

As for what’s next: keep growing. The newsletter, the consulting, the products. Everything I’m building right now is still early, and I want to see how far it can go.

Links & Resources

Connect with Daria…

My platform with AI resources:

https://app.aiblewmymind.com/

AI Migrator:

https://ai-migrator.aiblewmymind.com/

- a tool that exports your conversation history from ChatGPT, Claude, or Gemini into a portable profile, so you can switch between AI platforms without starting from scratch.

AI blew my mind

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🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

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🤔Is there a question you wish had been asked?
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Raghav started in fintech as a high-frequency trader, building algorithmic strategies in financial markets. His work was technical, niche, and hard to explain outside the industry.

He built depth early… but depth alone started to feel narrow.

During his MBA, as AI began to move into the mainstream, he saw a gap. Not just in the technology itself, but in how people were learning, applying, and talking about it.

He didn’t come from an engineering background and he didn’t have a clear roadmap. But he started testing, documenting, and sharing what worked.

Cash & Cache came out of that shift. Not as a polished brand, but as a way to think in public and build something alongside his career.

In this Playbook, Raghav shares how he started expanding beyond a single role, why he chose to write before he felt ready, and how he is building something that doesn’t rely on one path.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Raghav

Raghav Mehra is the co-founder of Cash & Cache, a Substack newsletter covering practical AI implementation and research.

He comes from a background in quantitative algorithmic trading and holds an MBA from IE Business School.

He writes weekly alongside co-founder Ashwin Francis for an audience of AI practitioners, product managers, and anyone trying to understand what AI actually means for how we work.

You can follow his work here →

Cash & Cache

Where capital meets code — exploring how AI is transforming businesses, markets, and value.

By Ashwin Francis

Raghav reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I come from a finance background — more specifically, a fintech finance background. I worked as a high-frequency equity trader for companies in the Indian financial markets. My background has been largely on the finance side, in fintech companies, creating algorithmic strategies and deploying them in financial markets. Basically, using algorithms to make money for my company. I got into this field because of my education in economics and finance.

One thing has always led to another in my life. I started out with economics, took a great interest in financial markets, and got the opportunity to be a trader. I’ve also been a CFA student — I cleared Level 1 and didn’t really get time to do Level 2 because I was working. And then I did my MBA as well, quite recently.

It was during my MBA that I realized I really liked another side of things — strategy, talking things through, working with people, managing strategies. I was also very fascinated by tech, which came from my fintech background. I graduated right when AI was breaking out. I joined business school just when ChatGPT had launched, and I realized this was going to disrupt a lot of spaces. There was an opportunity to fill the gap that still existed in terms of AI integration and learning.

I should also mention — I don’t come from a tech background. My job as a financial markets trader required me to adapt to some tech stacks and operational methodologies, so I learned basic programming like Python on the job. I don’t have a hardcore engineering background.

AI offered me a way to level up. I wouldn’t say match up to an engineer’s expertise — I still think engineers have a prominent role and can’t be fully substituted — but it was a great leveler. I was fascinated by tech but the steep learning curve made it difficult without an academic background. This is where I took a real interest in what AI could do, and how I got into working with AI, documenting workflows. And then I thought — there’s this platform called Substack where you can not just share, but write your thoughts, connect with other people, learn from other people. And here I am.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

I come from finance, so I know enough about the importance of diversification — you cannot put all your eggs in one basket. I realized with my old professional job that my role was too niche. Being a quantitative trader in equity derivatives — most people who asked me what I do didn’t even understand what that meant before I explained it. So I guess you have to build an identity that is not tied to your job, one that is inseparable from you.

Additionally, the external environment forces you to diversify. The job market can be really cruel and you have to prepare for bad weather. Diversification gives you more options at your disposal. But I’d also add — diversification is an ongoing process, at least for me. We are all trying to optimize for having the right mix.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

Adaptability is the key skill. If you can adapt to different cultures, methodologies, and philosophies, you can really position that as a competitive advantage. It’s also field-specific — if you’re in finance, you should understand not just financial concepts and principles, but also how to match them to outcomes and how to build an investment or trading thesis. So it’s a mix of field-specific expertise and a general openness to trying out new things.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

Visibility and credibility only come with time, so you need a lot of patience. There was no real framework for deciding how to use this platform. It was when my friend from undergraduate studies in economics, Ashwin, and I were having a chat, discussing this new and upcoming platform called Substack. We’d both been enthusiastic about AI and how it’s changing the world, and we both came from fintech backgrounds. So we thought, while we’re doing our day-to-day jobs, why not start a newsletter where we document our experiences and dig deeper into this space?

We thought — why not use this to improve our skill set and expertise? That’s how the visibility and credibility thing began. We started documenting and learned every day about what the platform was about, what kind of audience it caters to, and how to grow alongside other writers.

Substack is our bread and butter on this side of things. We both have been doing full-time jobs at different points. I was fresh off graduate studies, Ashwin was working as well. Right now it’s a small part of my income stream — we just enabled the paid tier. Hopefully we can grow further. Even if it’s small, I really enjoy being on the platform.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

Cash & Cache is primarily for AI product managers and practitioners — anyone who’s working with AI, building with AI, or filling the gaps in their own skill set or organizational architecture using AI. It’s also for people who want to learn more about AI and understand things that aren’t really highlighted out there.

We operate on two levers — the “Cash” lever and the “Cache” lever. That’s why it’s called Cash & Cache. We cover AI research and how anyone can implement AI well for their own workflow. The main problem we solve: people who have difficulty understanding AI for whatever reason, or who want to know how to adapt AI in any meaningful way. Our newsletter focuses on building that practical understanding.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

When we started, we had very little idea about blogging or content creation — our backgrounds were completely different before Substack. Getting to know the platform took time, but the bigger challenge was discovering our niche. At first we were talking about AI applications everywhere — FinTech, underserved industries, you name it. It seems specific and broad at the same time, because you want to cover areas that aren’t highlighted, but you also spread yourself thin.

It got easier as we built in public and started getting feedback. After the first few months, we began understanding what connected with our audience — what our first hundred subscribers responded to versus what felt generic or like things that were already everywhere.

The real realization was that it’s not just about finding a niche, it’s finding your take on something. Making it personal. Not being afraid of leaving some rough edges, because what I’ve realized is that people really value a personal connection in writing. That’s something we’re still working on. Nothing is perfect, and nothing ever will be.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

It’s been wonderful, honestly. It’s opened up our world. Substack introduced us to a microcosm of people who share interests, but with one thing that’s very different — people here love to cheer you on. It’s a breath of fresh air when you’re surrounded by social media apps that do just the opposite. In my MBA I learned this term — “enshittification” — the internet has been enshittified, and I really hope that doesn’t happen with Substack.

The best part of this journey has been the people. There are colleagues I’ve never physically met who are better than some of the people I’ve met in my professional career so far.

For advice: first, don’t be scared to hit publish. Don’t overthink it, don’t be scared of taking risks — that comes from my trading background too. Put yourself out there. Try to understand the platform, the audience, the landscape. But also be tactical — understand what’s missing in your space. If you’re writing about business, don’t write about what every other creator around you is already writing. Be different, be yourself. And be nice. Substack rewards genuine interaction, and honestly, being nice is a habit you can build here and carry into the rest of your life.

“What nearly made you quit, and what actually kept you going?”

Nothing on Substack has made me want to quit. In my trading career, that was a different story — it’s an extremely high-pressure environment, and the pressure really gets to you over time. But leaving that wasn’t quitting — I moved from a purely technical role to a more management-oriented one. You can quit a job without quitting your career.

On Substack — I check my dashboard more times than I’d like to admit. I think most creators do, whatever they say publicly. Some days the metrics move slowly and you have to remind yourself that vanity numbers aren’t the goal. Free subscriber counts are just a means to an end. The goal is the process, and believing that if you keep showing up and building something genuinely useful, the results will follow at some point.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Two things you have to identify. First, identify what you’re good at. Second, out of those things, figure out what the market actually values — what commands a premium. Your sweet spot is where those two overlap, and you also need to love what you do. When skill, demand, and genuine interest align, monetizing opportunities open up naturally.

For career pivots specifically: when you’re moving from field A to field B, find the overlapping skill sets and amplify that overlap. There will be skills you already have and skills you’ll need to develop. Focus on the ones that command a premium in the market. Keep yourself always learning, and build on what you’ve already done rather than trying to change everything completely.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

Honestly, I’m not as well diversified as it might seem. Substack is one platform — our publication, our product. A regular job is another — the backbone of my income. And I have a long-term investment portfolio I manage myself: a set of companies I believe in, compounding over time through capital gains and dividends. Nothing I’m actively trading day-to-day.

Not a big career portfolio yet. Regular income, Substack which I want to grow, and passive investments. I’m still at an early point in my career — I’m not a 40 or 50-year-old who has everything sorted. That’s just it.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

Moving to Spain for my MBA was the decision that changed everything. I’ve been away from home since I was 18, moved between cities in India, but relocating from India to Spain was a different kind of shift entirely. It wasn’t a smooth transition. But I like to embrace things as they come — different cultures, different opinions, different ways of doing things. I think it genuinely enriches your personality in ways that staying in one environment simply can’t.

Starting Cash & Cache last year was the other big one. Doing something on my own, in public, with real stakes.

What’s next: I want to work for myself. A diversified professional life where I’m not dependent on a single income source or employer — where I can travel, build things I believe in, and love what I do day to day. That might mean a proper business at some point. It will definitely still include Substack. The through-line is the same principle that’s guided everything else: diversify, stay adaptable, keep building.

Links & Resources

Connect with Raghav→

On LinkedIn

Cash & Cache

Where capital meets code — exploring how AI is transforming businesses, markets, and value.

By Ashwin Francis

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Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

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Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

She didn’t set out to build a nervous system-focused business.

She was trying to build a life that didn’t leave her exhausted.

Her early career followed a familiar pattern. Different roles. Better pay. No real sense of fit.
So she left and built something of her own.

A yoga studio. Full classes. Waitlists. A strong community.
From the outside, it worked.

But the model came with a cost.

Long weeks, constant output, and burnout that kept returning

…until everything stopped.

The pandemic forced Chloe into making a decision. Stay with the studio or change direction completely.

She chose to change it.

What followed was not a smooth transition. It was a period of breakdown, rebuilding, and decisions that did not always make sense at the time.

Inside her interview, Chloe shares what changed when she moved her work online, why she stepped away from the traditional model, and how she built a business around a more specific problem.

She also talks about writing, leaving social platforms, and what happened when she went all in on Substack.

This is not a clean pivot.

It is what happens when you evolving your work long enough to find what fits.

If your career looks right on the surface but feels off underneath, this one is worth a read.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Chloe

Chloe Markham is the writer behind Joyful, a Substack for sensitive, high-achieving people who are tired of living in constant overwhelm and want to feel better in their own lives.

A yoga teacher and nervous system coach, Chloe moved from running a busy in-person studio to building a quieter, online business focused on regulation, energy, and joy. Her work now centres on helping people shift out of survival mode and into something more sustainable.

She writes for people who look like they are coping on the outside but feel exhausted underneath. She writes for those who know something needs to change, but do not want another system that pushes them harder.

You can follow her work here →

Joyful with Chloe Markham

Get nervous system relief, real-life regulation, & joy without hustle every single week. Expect actionable strategies to build resilience, find calm, and live a more joyful life. Because life's too short for anything less.

Chloe reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

It’s the classic tale, isn’t it: I worked in corporate and quit everything to become a yoga teacher. Except that particular corporate gig was just one in a line of many.

After graduating with a Marine Geography degree from Cardiff Uni, I worked offshore as a hydrographic surveyor. Hated that, so then I worked as a marketing exec. As an office manager. A copywriter. A marketer…

But I became overwhelmingly despondent. The money for some of these jobs was brilliant, but I was deeply miserable. The stereotypical turning point came when I qualified as a yoga teacher in 2016, began teaching, and had waitlists and queues out the door within six months.

I opened a studio in 2018 and it quickly became a thriving community — packed classes, loyal clients, and a real sense that I’d finally built something meaningful. Today yoga is still part of my work, but it’s just one of the tools I use in helping women find their magic and their joy.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

The Covid pandemic was a slap-in-the-face overnight realisation that I needed to pivot. I’d been running my studio in York, my hometown, for about a 18-months, and it was starting to turn an actual profit. Then March 2020 came.

I shifted our classes online overnight, and within a couple of months I was forced to make the decision whether to commit to the studio, or change my entire business model. I chose the lesser of two evils: I changed the business model.

That shift was the start of a few years of upheaval. I left a toxic relationship not long after, and I kept my business going by the skin of its teeth as I totally broke down. But from that rock-bottom I was able to rethink what I want this whole thing to be.

Before 2020 I was teaching around 14 hours of yoga a week and burning out every couple of months. But now I’m running a successful online nervous-system-focused business, helping women shift from survival to thriving in my easy going style.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

I wouldn’t say I’ve had a previous career as such — it was all so random as I searched for meaning in my work — but working in marketing and as a copywriter has been unbelievably lucky for me. To run your own business is to wear every hat ever made, it seems. To have marketing and copywriting abilities is a huge advantage, and for that I’m grateful every day.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I slogged away for years on the traditional social platforms. And I’d say that contributed to my many burnout episodes. I’ve never felt aligned with them, and it was only in 2024, following the advice of a great coach I had at the time, to experiment with Substack. I was a writer, after all, and that’s the platform for writers.

It wasn’t long before I ditched everything else and decided to go all in on Substack as my prime social platform, and it worked. In less than a year my audience grew by over 300%. Using only Substack and no traditional social platform isn’t only a smart idea for me energy-wise and growth-wise, but it feels like integrity: if I’m helping women step out of burnout and survival mode, building my own business somewhere calmer and slower made far more sense than trying to win the social media attention game, which is way more toxic than we give it credit for.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

I help brilliant, sensitive, high-achieving women who are burned out and stuck in survival mode find relief and joy again.

Through nervous system restoration and joyful practices, I help them get their energy back, shift their perspective, and start living a life that actually feels good.

Because life’s too short to spend it exhausted.

“What turned out to be harder than you expected when you started… and what was easier than you imagined?”

What’s been harder than I imagined has been a trusting of my gut. Trusting my gut when it told me to close my successful yoga studio and move online. When I shifted away from a yoga studio model. When I left that relationship.

If I told my younger self, even just a 5-year-younger self, that I’d be coaching and supporting and writing the things I do today, I wouldn’t have believed it. It’s taken a lot longer than I imagined to lean into my magic fully. A decade, honestly. And it’s been nothing but learning. Every pivot — moving online, focusing on nervous system work, going all-in on Substack — required trusting instincts that didn’t always look or feel conventional.

Something easier than I imagined? I’m not sure about this one. Although I would say that waking up every day and running my own schedule (I’m currently on a train as I write heading to see a friend who needs some support) is the biggest joy of working for myself. I wouldn’t go back.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

A joy, honestly. I’d say persistence is your biggest superpower with any angle of your business, really, but certainly Substack. Be persistent with Notes, with your writing, trust your voice, don’t worry about what everyone else is doing or the crap that everyone sells that claims to make you go ‘viral’. Just show up, be consistent, and Substack will reward you.

“What nearly made you quit, and what actually kept you going?”

Leaving a toxic relationship, moving in with my mum, closing my brick and mortar studio and feeling the loss of clients post-pandemic… that’s been tough. Really tough. What kept me going, honestly, was always a desire to do things my own way and help women like me find more joy again. So I kept going. I pivoted and pivoted and pivoted again. And it’s that persistence that’s got me where I am today.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Do it. I mean, be conscious of your responsibilities and financial situation, but experiment immediately. Weekends or evenings or whatever: test it out, see what happens, and follow what feels good. If it’s just about money, I’m not saying it’ll fail, but it won’t do as well for you in your life compared to a project that you believe in down to your bones. That’s what keeps us going, I think.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

As well as my Joyful membership and signature program, Joy Unplugged, I also work with a handful of founders and entrepreneurs, helping them run their businesses like sane, calm, regulated humans.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

Leaving that relationship, probably. I wouldn’t be where I am today if I stayed. Leaving him allowed me to learn what trusting myself feels like again. Hard journey, but a totally joyful one.

What’s next? Who knows, eh?! But there’s definitely in-person collectives in the future of what I do, because there’s nothing I love more than running an actual real-life party.

For now, though, I’m focusing on making Joy Unplugged and my paid membership impactful and life-bettering and I’ll see where that takes me. I’m definitely one for keeping things fluid! The only constant is helping people live with more joy and a calmer nervous system — the shape that takes will always keep evolving.

Links & Resources

Connect with Chloe:

Joy Unplugged: https://www.chloemarkham.co.uk/joy-unplugged

Her website: https://www.chloemarkham.co.uk/

Joyful with Chloe Markham

Get nervous system relief, real-life regulation, & joy without hustle every single week. Expect actionable strategies to build resilience, find calm, and live a more joyful life. Because life's too short for anything less.

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Read More

Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

He didn’t set out to build an online business.

He followed something that worked.

A coaching method. A relationship. A simple marketing idea that got real results. From there, things started to open up.

But not all at once.

There were long stretches where nothing seemed to move. Writing that got little response. An email list that barely grew. Work that felt like effort without traction.

Instead of stopping, he adjusted.

Inside, Rodney shares what he changed when things weren’t working, and how a shift in how he set goals gave him a way to move forward, even when the path wasn’t clear.

He also talks about what actually led to growth, and why some of the things people rely on didn’t work for him.

This is not about quick wins.

It’s about building something that lasts.

If you have expertise and want to turn it into something people value, this one is worth your time.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Rodney

Most people who transition from teaching to online business talk about escaping. Rodney Daut doesn’t frame it that way. He followed his curiosity — into a coaching method, into a friendship, into a marketing experiment — and the career just kept unfolding from there.

He’s the writer behind Course Builder’s Corner, a Substack for coaches, consultants, and writers who want to turn their expertise into products people actually buy. He’s also the creator of the Atomic Course Blueprint, a framework for building tiny courses that grow your income without overwhelming you or your students.

His work is built around a simple idea: that coaches, consultants, and writers already have what it takes. They just need help packaging it, positioning it, and getting it in front of the right people. That’s what Rodney does — for clients, and increasingly for himself.

You can follow his work here →

Rodney reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

What’s my professional background? I was a public school teacher. To help myself make personal changes, I learned a method called the Lefkoe Method that made a difference in my life.

Then I became friends with Morty Lefkoe, who created that coaching process. I noticed that hardly anyone knew about them and their business was struggling. So I did some research and helped him come up with an idea that helped him grow his business. He said, “Hey, look, can I hire you?” and I said, “Yes.” That’s how I got started in online marketing, online writing, and online business building.

The thing I helped them do was say, “You’re teaching a great coaching method, but if you have a niche, it’s easier to promote it.” We came up with the niche of fear of public speaking, and when we started pursuing that niche, he was getting great results with the clients; they ended up with a waiting list of 20 clients. So if you signed up you’d have to wait a couple of months to work with them. Anyhow, that was my first success in marketing, and I was really proud of that.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

I can’t point to a single moment that had me think, “It’s time to diversify,” but maybe a few years after Morty died I decided I wanted to get this business to a place where I could leave it and know it would run well and be successful. I kind of want to go off and do my own thing, so I suppose that was it. It’s not really a sign, but things change, and I’m not the kind of person who wants to do the same thing forever.

Another change during the pandemic was this: we grew our business quite a bit, but it was all on me. I was marketing the courses, developing the courses, and running the courses. We had daily feedback in our courses, so I was working until 10 p.m. whenever a course was running. That wasn’t sustainable, and that was five months of five cohorts a year. Luckily, because those cohorts were so effective, we ended up with students we could certify and train to help with that load. Now they do almost all of the feedback, and I still do the curriculum design and the marketing. That frees me up to do a lot of other things. Tasks for the Lefkoe Institute, but I also have time to grow my own business and still have a life.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

I’ll be honest, I don’t think there are any truly unexpected skills involved, because nearly everything I learn in that business is something I can use in my own venture. For example:

• I build products for the Lefkoe Institute; I build products for my own business.

• I write sales copy for the Lefkoe Institute; I write sales copy for my own business.

• I build email campaigns for the Lefkoe Institute; I build email campaigns for my own business.

It’s not really unexpected, but one powerful transferable skill is the ability to coach people, because that is one of the most lucrative things you can do: coaching others and helping them achieve results.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

It wasn’t really like a decision, or maybe it was. Here’s what happened: I was writing on LinkedIn. I didn’t see myself making a lot of progress there, and I started to think that social media might not pay off for me.

What I decided to do instead was create an e-book with a bunch of other popular creators online who had figured out how to grow their businesses. I called it Profitable Play Books. I interviewed these people, and luckily I knew them because I’d interacted with them online. Some of the popular ones I’d become friends with agreed to participate because they already know me. That openness encouraged others I didn’t know as well to work with me as well.

I ended up finding a lot of them on Substack. When I interviewed them, many said they got a lot of growth from Substack Notes, so I started writing notes. I believed these notes could help grow my subscriber base, but most didn’t.

What ended up happening is that whenever I would have a Substack live with someone, my email list grew.

Although I grew my email list considerably from the free e-book I created, I also gained at least half of that growth from Substack live sessions with different creators. This was pretty awesome.

That’s why my main platform is Substack now, because much of my growth came from meeting people live or doing guest posts on other newsletters.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

The people who benefit most from my work are coaches, consultants, and writers. Coaches and consultants benefit because they have expertise, love to talk, and are very good at it. They just need to translate that into products they can sell, and that’s what I help them do: figure out what products they can sell, who they can sell them to, and create the campaigns to sell those products.

For writers, they already know how to write. I teach them to use their writing skills to create products that teach people how to do something valuable, something they are already an expert at. The problem they all share is that they have valuable expertise but don’t know the best ways to profitably contribute to others with that expertise. That’s what I help them do.

“What turned out to be harder than you expected when you started… and what was easier than you imagined?”

The hardest thing is to keep going when hardly anyone responds to your work. When you put in effort, it bursts your bubble to spend time and energy on something and see crickets with no response. That’s the hardest thing: how do you get beyond that? How do you reach a point where you’re getting a response?

That was part of what made me write my ebook. I thought, I don’t think I’m going to get my email. This isn’t going to get any bigger. Every time I gained more people on my list, more people would unsubscribe, so it wasn’t really growing. It kept going like that for months, and I told myself, I have to do something.

I think the hardest thing is turning those uncomfortable feelings into productive discomfort that helps you do something. I guess that’s the hardest part.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

The advice I have is simple: set goals. I know it’s not innovative, but I’ve looked at goal research, and goals can be powerful. There are two types of goals, and it’s important to know both because each is useful in different situations.

People don’t set goals mainly because they only know about one type: outcome goals. Almost everyone thinks, “Set a goal like you want to grow your email list by 1,000 people or make a certain amount of money.” A reason people don’t like to set those goals is that they’re not confident they can reach them or they don’t know how to do it. They ask, “What’s the point?”

Whenever you don’t know how to achieve a goal, that’s when you should set a learning goal: to figure out the specific strategies and skills you need to learn. You still follow the other elements of good goal setting, like a time limit and planning. Many people do things without planning. You have a goal and you have a plan, and if that goal is a learning goal, you set a plan to help you win. You have an outcome goal because you think you already know the skills required to achieve that outcome; then you set an outcome goal and you plan to achieve it.

Those are the things I would tell people, and the idea of learning goals is to help more people understand them.

“What nearly made you quit, and what actually kept you going?”

I’ll be honest, I have not considered quitting.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

If you want to monetize your skills in a more flexible way, setting learning goals is extremely useful. Locke and Latham, who conducted the original goal-setting research, were the ones behind the SMART acronym used to summarize that work.

They later found that if you don’t know how to do something, you should set learning goals. For example, say, “I’m going to learn three strategies to help me do X, Y, or Z.” If you don’t know how your skills can transfer to something else, that’s useful to realize. You might set a goal like, “Let me find five different ways my skills could transfer to another career or to a business I could build,” give yourself a time limit, and pursue it.

Then you might ask, “What strategies could I use to find those ideas?” You could talk to five or ten people, listen to podcasts, read books, or hire a coach. You begin to generate strategies instead of hoping one day the ideas will strike like lightning.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

I’ve tried a lot of things. I spent a lot of time on Twitter and LinkedIn, but right now my main focus is Substack. My income streams come from coaching, ghostwriting, and market strategy I do for clients. For market strategy, I also write copy and help my clients put together their workshops and programs. These activities all work together, centered on creating a quality learning experience for clients and customers. Of course, to create that experience you have to attract people through ethical marketing and ensure that the promises are delivered.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

There are at least two turning points that made a difference for me.

The first was achieving my first major marketing success: courses I promoted for the Lefkoe Institute sold out in a matter of hours. This success fueled the confidence I needed to begin offering my own coaching services, helping others market their programs.

Another big change is when I joined Ship30for30, that got me on the road to building my own email list and then communicating with that list regularly. I had written for 30 days straight, so that means I could keep coming up with more newsletter ideas every week to keep people interested. I learned that people liked the idea of building tiny courses, and that gave me confidence that I had an idea that was worth pursuing.

Links & Resources

Connect with Rodney…

On LinkedIn

On Twitter

Products:

https://rodneydaut.substack.com/p/featured-products

Services:

https://rodneydaut.substack.com/p/services

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Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

James’s background is writer-first. He built a freelance career around client work and content, learning structure, rhythm, and voice the hard way, through years of paid work for real clients with real expectations.

But it’s what happened when AI went mainstream that makes his story worth paying attention to.

He didn’t do what most displaced creatives do. He made a decision that quietly reshaped everything, and the path he took from there is not the obvious one.

Today he runs a growing Substack community, sells digital products, and works with founders in ways that didn’t exist in his vocabulary a few years ago.

In this Playbook, James talks about what freelance writing actually prepared him for, what the breaking point really looked like, and how he built something new without a roadmap for any of it.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About James

James Presbitero is the founder of Unpromptable and the creator of the Unpromptable newsletter, with over 2,000 subscribers and a growing audience across Medium and LinkedIn.

A freelance writer turned AI systems designer, James spent years mastering his craft before AI reshaped the content industry entirely. Instead of stepping back, he rebuilt from the inside out, developing a framework for using AI in ways that make founders and creators more distinct, not less.

He works with founders and business owners to build proprietary AI systems designed around their specific voice, mission, and way of working.

He writes for the people who refuse to be replaced. He writes for builders who want to stay irreplaceable.

You can follow his work here →

Unpromptable.

Helping founders, creatives, and professionals become irreplaceable in the Age of AI || Subscribe: forever free 2x deep dives, community events, and free Active Prompt Vault (+ more AI & marketing tools).

By James Presbitero

James reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I was a freelance writer.

I’d built a career around client work and content. Nothing flashy, but it was mine, and I was good at it. Then tools like ChatGPT went mainstream, and the projects started disappearing. Clients who used to hire me to write were suddenly wondering why they should. It happened faster than I expected.

The financial hit was real, but the bigger question was the harder one: did I spend years learning a skill that no longer had a future?

After sitting with that for a while, curiosity took over. I stopped defending what I used to do and started actually studying AI—what it could do, where it fell short, and what it could never replace. I rebuilt my writing systems around it, tested it obsessively, and started asking deeper questions about voice, authenticity, and what genuine human creativity looks like when AI is in the room.

That process became Unpromptable, a newsletter built on the belief that AI works best when it amplifies a clear human mission, not when it replaces one. I work with founders, creators, and business owners to help them become irreplaceable in their field.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

When AI made all my clients disappear, I knew I needed to do something. At first, I wanted to write online to have a way to show potential clients that I'm better than the chatbots, but eventually I slowly realized I had to adapt my entire method and principles, and with it—my income streams.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

Years of freelance writing meant I understood the craft before the tools existed to shortcut it. I knew what a good sentence felt like. I understood structure, rhythm, flow — not perfectly, but enough. And when AI arrived, that foundation turned out to matter more than I expected.

AI magnifies what you bring to it. If you understand writing, it helps you write better. If you don’t, it just helps you produce more of the same mediocre output, faster. I’d spent years learning the principles and that gave me something to actually work with when the tools arrived.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

Medium was the natural starting point. My strength was longform, and Medium rewards longform — so it made sense to begin there. Over time, I found a pace that worked, carved out a niche, and started monetizing. Not life-changing money by all means, but proof that the model held.

But, while Medium is a great place to be read, it’s not a great place to build relationships. And at some point, being read wasn’t enough, I wanted a community with real ties, real conversations, people who were genuinely invested in the same problems I was trying to solve.

That’s what pushed me toward Substack.

The two platforms now play very different roles within my ecosystem. Medium (plus LinkedIn, recently) are where new people find me — discovery, reach, top of funnel. Substack is where the real work happens. It’s my primary community, the place where readers become clients, and where the Unpromptable philosophy gets to breathe and grow in a more intentional space.

Each platform does one thing well. The key was stopping myself from asking all of them to do everything.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My work is for mission-driven founders and business owners who know AI can help them — they just haven’t figured out how yet. They’re not technical people. But they’re curious, they’re paying attention, and they can feel the pressure of a landscape that’s shifting under their feet.

What they’re afraid of isn’t AI itself. It’s becoming indistinguishable from it. They want to use AI without disappearing into the noise — without their content, their brand, and their business starting to look like everyone else’s.

That’s the core of what I teach: Unpromptability. The idea that AI should make you more irreplaceable, not less. More distinctly yourself, not a polished, generic version of whoever wrote the best prompt.

And for founders who are ready to go further, my core offer is building it for them — proprietary AI systems designed around their specific business, giving them a real edge. A conversion moat. An operational moat. Something competitors can’t just copy because it was built around something no one else has: their unique mission, voice, and way of working.

The goal is to help them use new technology in a way that makes them impossible to replace.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

Oddly, it was easier than I imagined to get clients to pay for this new offer. What’s difficult is maintaining my marketing pace while ensuring I deliver quality service to them.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

It has been everything. Boring, fun, scary, and exhilarating.

My advice: focus on the long game, and don’t let the early slog overwhelm you. Focus on building consistency and communicating with your ideal audiences, really building a relationship with them.

“What nearly made you quit, and what actually kept you going?”

The early slog. I wasn’t one of those people who hits their stride by month three. It took closer to six. Six months of publishing, thinking, refining, and wondering whether any of it was actually doing something.

What kept me going was my dedication to my mission: I really wanted to explore Unpromptability because I think it’s becoming very important in today’s world. Also, I really wanted to find my community in Substack.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

The early slog is real, and no amount of advice fully prepares you for it. So the first thing I’d say is: go in knowing it’s a long game, and make peace with that before you start.

The second, more practical thing; don’t burn your bridges while you’re building the new thing. Growing an online presence that generates real income takes time. More time than most people expect. If you can build it alongside an existing source of income, do that. Use the runway. It removes the desperation that makes people rush, cut corners, or quit too early.

The rewards come. But they come later than you want them to, and only to the people who were still standing when they arrived. It’s worth it.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

The ecosystem is pretty simple, and intentionally so.

People find me on Medium and LinkedIn. Those platforms do the discovery work — reaching cold audiences, building initial trust, pulling in people who are encountering Unpromptable for the first time. From there, I have digital products on Gumroad, priced between free and $15, that give people a low-friction way to go deeper. Discounts and campaigns make them easy to say yes to, which matters more than the revenue at that stage; it’s about building trust with someone who doesn’t know me yet.

Once they’re in the newsletter, Substack takes over. That’s where the relationship develops. Where I write with more depth, more honesty, and more specificity about what I actually do and who I do it for. It’s where readers become community, and where community eventually becomes clients.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

The decision that changed everything was the simplest one: starting. To put ideas into the world consistently and see what came back. Everything else grew from that.

What’s next is the natural evolution of everything I’ve been building toward. A lean agency — helping founders and businesses build unique, proprietary AI systems that give them a real, lasting edge. Bespoke, truly-powerful systems built around who they are and how they work, so that what they build becomes genuinely hard to replicate.

Links & Resources

Connect with James →

Gumroad: https://presbitero.gumroad.com/l/wfnnnf

Medium: https://medium.com/@jamespresbiterojr

LinkedIn: https://www.linkedin.com/in/jamespresbitero2022/

Unpromptable.

Helping founders, creatives, and professionals become irreplaceable in the Age of AI || Subscribe: forever free 2x deep dives, community events, and free Active Prompt Vault (+ more AI & marketing tools).

By James Presbitero

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Read More

Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

Noemi trained as a lawyer, completed both her Bachelors and Masters in law, and then went on to spend 15 years working in and with IT companies, specializing in commercial, privacy, and IT.

But it is what happened when she burned out that makes her story inspire.

She didn’t go back to the office. She didn’t look for the next legal role. She did something that most lawyers with her experience never seriously consider, and it changed the shape of her career entirely.

Today she runs two Substack publications, organizes Do Sessions for creators who want to build something of their own, and sells legal templates and Canva kits while she sleeps. Writing became the thread connecting her legal expertise, her systems, and the audience she built from scratch.

In this Playbook, Noemi talks about how and why she pivoted away from her 15 years in IT law, why she started writing in public, and how she built a portfolio career that most lawyers never think to try.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Noemi

Noemi is the creator of Me Time and The Fine Print, two Substack publications for creators who want to build a digital business and protect what they build.

A trained lawyer with 15 years of IT law experience, Noemi burned out, reclaimed her time, and built a portfolio career from scratch, selling legal templates and Canva kits and running Do Sessions for creators ready to build something of their own.

She writes for the people who are done relying on a 9-5. She writes for the builders.

You can follow her work here →

Me Time: Pause - Decide - Do the Thing!

🎈Good things come to those who DO. Think clearly. Write boldly. Build a portfolio career around what you actually enjoy. Join Me Time Do Sessions where ideas become published work & additional income. 🎈Me Time: 40 and just getting started.

By 🎈Noemi from ME TIME 🎈

Noemi reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I am a trained lawyer and did both my Bachelors and Masters in law, specializing in commercial, privacy, and IT law. I’ve worked in IT companies or with them for the past 15 years until, one day, I burned out. I did not know if I wanted to be a lawyer again...

I did not find good enough support for burnout recovery in Denmark, where I live, so I started a journey of self-discovery that I started calling “Me Time.” As a mom, “me time” was rare and became my holy grail but also the thing my psychologist recommended I take to recharge so I can show up fully for the people around me.

That was the spark. Reclaiming some of the time of each day for me.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

The path to a portfolio career showed up gradually... like, really gradually. But being in IT, you could see very early signs of employees being expendable, so building a personal brand became part of my hope to build a reputation that is not hinging on just the referrals from bosses and colleagues.

I wanted to build a portfolio of my work and knowledge on LinkedIn. And so it all began with carousels on LinkedIn.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

My main superpower as a young lawyer working in a dynamic IT company was getting stuff done with a lot of creativity, thinking out of the box. Ex-colleagues still talk about what I’d achieved. That’s a nice pat on the back to get.

And today? Today I organize Do Sessions as my main offering for all Me Time Subscribers. I say I am not a Substack guru, far from it... but that I am a DO-ru, hehe!

The ability to communicate complex legal matters in a way that people with a non-legal background can understand while also keeping the business growing was another thing. Legal advice and acting like a red time restricting your movement. -- Good lawyers create corridors where law and business work together and goals are achieved.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I started on LinkedIn because there was no other place legal content would really fit. I thought.

I used a lot of my free time to craft these amazing slides, but my growth was really slow. I did not feel appreciated, but I did get some visibility in Denmark and got invited to speak (for free) at events.

I also got my first legal leadership job off the efforts I put on LinkedIn. I joined Substack to get a course from a lawyer writing here. Did not know what it was... but then I slowly realized, and because I wanted to start a podcast, I decided to start something here.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

The answer, I feel, is still developing. But the core of my offer is aimed at people that want to build something bigger than a 9-5, and for that they need to reclaim some time and learn skills.

I have the he Do- sessions I organize but I also sell shortcuts inspired by my legal career and my systems and templates for creating a visual identity for the platforms you are one. Terms and conditions to protect what you build for your Substack audience. I also teach in do sessions how to create digital products and promote them on your social media.

So I do a bunch of things! I love them all! The most valuable, I think, are the legal terms that my paid subscribers to The Fine Print get.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

I think the hardest thing is moving forward with no feedback. That it feels for a long time like you are shouting in the abyss! Easier is getting everything figured out little by little about running my own business. I thought I was a lawyer... turns out I was a businesswoman all along!

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

That’s the million-dollar question, isn’t it? I think as much as the growth experts would claim there are ways to grow... Each Substack can become a small business in its own right. But no one can honestly promise that anyone will succeed just by following their advice.

Success depends on judgment, effort, positioning, timing, and the person behind it. Anyone guaranteeing results for everyone is selling certainty that simply doesn’t exist.

They say I help you grow your Substack, and suddenly that feels possible. Most people wouldn’t believe them—and they shouldn’t. I think there are limits to how much that advice helps.

The most useful thing I have learned is this:

• Do, write and create on topics you absolutely LOVE! Without this, doing just for the love of making a buck doesn’t really work, and you will give up easier.

• Your niche (and you need one; I have learned the hard way) needs to be directed at helping people. The faster you can help people (or delight them), the more successful you will be.

• The thing you start with may very well not be the thing you end up doing as your Substack publication/offering, side gig. For many there is an exploration and discovery phase.

• Consistency is great, but it needs to be tempered by small pivots towards what your audience wants. I did not start selling Canva templates, but everyone loved my graphics, so I started doing workshops and selling my templates. People love how fast they can give their Substacks a makeover and make their publications stand out! And I love teaching it. But I am a lawyer, and that was not in the blueprint.

“What nearly made you quit, and what actually kept you going?”

Today was an “I-nearly-quit-this” kind of day. So I gave myself the day off and did nice things to cheer myself up. I know that when you build something of your own, you will go through valleys as well as highs. And today was a lower point. That’s ok.

At another point, both Me Time and The Fine Print were both on Substack and it felt amazing! You get wins, and you get disappointments. These days, I was feeling down because I felt I’ve been working so hard for what feels like very little in return...

Also, it’s mentally and psychologically difficult to see people writing “Hey, I am new to Substack” and getting 5k likes and 300 overnight subscribers and genuine useful notes and posts getting 5 likes. It can feel like a real dagger to the heart. That’s why you need to do something you really love and believe in. Otherwise, you will find plenty of occasions to quit.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

I advise everyone who will listen to not rely on just a 9-5. Build something else.

Build it on your professional skills or on your hobbies, your weird obsessions; build something of your own. It does wonders for your self-worth and self-confidence.

At one point you can even start making money from it. I wish I could say it happens overnight. But it does happen!

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

I am on Substack and sell digital products, especially Canva Kits for Substack on Gumroad. This is my Gumroad Profile there with my current offerings.

I then market terms and conditions for your Substack via the Fine Print.

In Me Time I organise Do Sessions for all subscribers (like workshops with goodies and Q&As) and for the paid tiers they get really cool workbooks with templates and reading material and shortcuts and the Do Session recordings so they can work and develop their digital business at their own pace. They also get to book me for short 1:1 sessions during my Office Hours if they have questions. I love helping! This is more than enough for me now.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

Definitely stepping into creating digital products. Finding innovative ways to help people really fast gives me a lot of satisfaction! Then you make money while you sleep! It is really cool!

What is next is

1. A big collab with Ana Calin from How we Grow where I will be giving a legal workshop to her cohorts and

2. Then a few more Do sessions followed by

3. Maternity leave. I am 33 weeks pregnant so I am now preparing the publications to stay afloat while I take some time with the new baby.

Links & Resources

Connect with Noemi→

On LinkedIN

Do Sessions Calendar

Gumroad Substack Template Shop

The Fine Print

For Substackers who mean business! 🔍 I read the legal fine print so you don’t have to & spot the risks most people ignore. 🔍 For my paid tiers, I offer custom legal T&Cs to protect your business and earnings.

By Noemi from The Fine Print

Related Articles

Me Time

4 Things That May Get You Booted from Substack

5 Substack Settings to Make your Newsletter Look Professional

The Fine Print

Copyright protection is affected if you use AI to write!

Concerned about your address showing up on Stripe invoices?

Read More

Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

He spent three decades working for churches and charities. At 51, with no writing experience, no marketing background, and no business skills, he decided to start over. Most people wouldn’t. He did.

For seven months he wrote into silence. Four posts a week. Almost no response. No readers, no income, no sign it was working. He nearly quit.

Then one article changed everything.

What followed was not luck. He studied what worked, tested it, and kept going. Slowly, readers showed up. Then paying customers. Then came the moment he realized he didn’t need his 9-5 anymore.

Derek did this later than most people would dare to try. That turns out to be part of the story.

In this Playbook, he shares exactly how he did it, what nearly stopped him, and what he learned that nobody tells you at the start.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Derek

Derek Hughes wrote his first word online three years ago. Today he runs the Irresistible Writer, one of Substack’s go-to destinations for writers who want to build an audience and earn from it.

He is a former charity and church sector worker who rebuilt his career from scratch at 51, with no writing experience, no marketing background, and no business skills.

Today he teaches writers how to get noticed, grow an audience, and turn their ideas into income, without aggressive marketing or hype.

You can follow his work here →

The Irresistible Writer By Derek Hughes

Showing writers how to use words to make money and change lives. Proven tips to build an audience online.

Derek reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I spent three decades working for churches and charities. Eventually I landed in a role that wasn’t especially demanding, and I suddenly had some spare headspace. I decided to experiment with writing online, initially on Medium.com.

It started as a hobby — something creative and fun. But fairly quickly, it began to turn into something much more serious.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

After about three months of nobody reading my work, I realised something had to change. I’m quite competitive, so instead of quitting, I decided to figure out how audience-building actually works.

I began studying what the bigger writers on Medium were doing and experimenting with different styles and techniques.

For seven months I published four posts a week and saw almost no progress. I was close to quitting — and then one article went viral.

That’s when everything changed. That was the moment my new career really took off.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

I started with no writing experience. I was terrible at writing at school. I had no marketing background and had never worked in business before. Starting again at 51, I honestly thought I had no chance.

But then something interesting happened. I mentioned my age in one of my articles and the comments lit up.

People seemed to connect with the idea that if I could start again at 51 with no experience, maybe they could too.

It turns out life experience, empathy, and understanding people are real advantages — even if you don’t have traditional credentials.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I discovered Medium after reading a Nicolas Cole book, so I just began writing there. As I started growing and earning, other writers encouraged me to move to Substack.

That’s now where I mainly write.

In my view, it’s the best platform for writers at the moment — and I’ve tried most of them. It gives you ownership of your audience and multiple ways to grow and monetise.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

I help people who have something meaningful to say — people who want to help others and earn money doing it.

I teach them how to write in a way that gets attention, how to build an audience, and how to turn that audience into income through digital products and services.

It’s especially for people who don’t resonate with aggressive, sales-heavy marketing. They want to serve ordinary people, not become internet hype machines.

I help them do that in a practical, structured way.

“What turned out to be harder than you expected when you started… and what was easier than you imagined?”

Building an audience was much harder than I expected. Seven months of writing into silence nearly broke me. It’s very difficult to stay motivated when nobody seems to care.

But once I built trust and readers began paying attention, making money was actually easier than I thought.

When people trust you and you solve a real problem for them, monetisation becomes straightforward.

My first product was The Ultimate Headline Toolkit. I had around 580 subscribers and made about $1,700 in seven days.

That was the moment I knew an online business was genuinely possible.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

Substack is a brilliant platform for writers. But it’s more complex than others because it has so many features — which can easily become overwhelming.

When I coach writers, I tell them to focus on three things:

1. Daily Notes (for discovery)

2. Recommendations (for compounding growth)

3. One high-quality post a week (for deepening trust)

Everything else is noise.

Do those three things consistently and you will grow.

“What nearly made you quit, and what actually kept you going?”

What nearly made me quit was the silence. Writing consistently and getting no response is tough.

What kept me going was advice from other creators who talked about compounding. They said the work you do now pays off months later.

So I focused on process goals—how much I would write, how often I’d publish—and measured that instead of results.

I treated it like seeds going into the ground. You don’t see anything at first. But if you keep planting, eventually something breaks through the surface.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Start on Substack. Expect it to be hard. Expect it to take time.

But if you’re serious, go all in. Write consistently—ideally daily. Half-commitment rarely works.

I also invested in courses and coaching early on from people I trusted. That accelerated my learning dramatically.

Buy from people who are already where you want to be. It will shorten the path.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

I run a monthly masterclass programme with a community of writers. I also run live cohort intensives focused on growing on Substack or building a business from scratch.

Alongside that, I sell standalone digital products and toolkits. I also offer a limited amount of one-to-one coaching.

All of it connects back to the same core mission: helping people build an audience and turn their ideas into income.

Each part supports the others.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

The decision that changed everything was committing fully instead of treating it like a hobby. Once I decided to take it seriously, everything accelerated.

Going forward, I want to keep things simple: help people, provide real value, build useful tools, and enjoy the process.

That’s the path I’m staying on.

Links & Resources

Connect with Derek…

From Zero to Paid - Build an Online Business from Scratch

The Irresistible Writer By Derek Hughes

Showing writers how to use words to make money and change lives. Proven tips to build an audience online.

Related Articles

Welcome to The Irresistible Writer

The Real Reason No One Is Reading Your Writing

The Most Ignored Growth Lever on Substack

5 Ways To Make Money On Substack (How I Make $5000/Month)

Read More

Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

She didn’t come from tech. She came from the work of making institutions fairer, one policy, one conversation, and one training at a time.

Then AI started showing up in the systems she knew best. And she noticed something most people in the room were missing.

What she did next is the playbook.

Inside, Cristina talks about the moment she realized her background wasn’t a liability in AI spaces; it was the thing those spaces were missing most. She gets into the identity friction of stepping into a field dominated by engineers and lawyers without a technical degree. And she’s direct about what it actually takes to build credibility when no one handed you a seat at the table.

She also shares what surprised her most about starting The Responsible AI Brief, what she had to push through, what she’d do differently, and where she’s headed next.

If you’ve ever wondered whether your non-technical background belongs in a technical conversation, this one is for you.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Christina

Cristina is the writer behind The Responsible AI Brief, a newsletter about AI ethics, governance, and civil rights thinking.

She is an Equal Employment Opportunity Specialist, DEI practitioner, and humanities-trained writer who is building her career at the intersection of bias, policy, and AI safety.

Today, she brings years of equity work into rooms that have rarely seen it, translating the human cost of automated systems into writing that doesn’t require a technical degree to understand.

You can follow her work here →

The Responsible AI Brief

Weekly newsletter delivering AI ethics analysis and practical guidance for leaders, HR professionals, and concerned citizens.

By Cristina

Christina reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

My background is in the humanities, the kind of education that teaches you to read between the lines and think critically, and I am grateful for that. From there, I built a career in Diversity, Equity, Inclusion (DEI) and Equal Employment Opportunity, which, at their core, are about systems and structures.

For years, that meant working within institutions, navigating policy, helping organizations understand that equity isn’t a checkbox, it’s a design problem. I got good at translating complex frameworks into plain language, at sitting with people and facilitating difficult conversations.

What I didn’t expect was that all of that work would eventually lead me here, writing about artificial intelligence. But in hindsight, it makes complete sense.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

It wasn’t one specific moment, it was more like a slow accumulation of noticing.

I kept seeing AI come up in hiring tools, performance management systems, and in the workplace in general, and I kept noticing the same thing: nobody was asking the right questions. The technologists weren’t thinking about disparate impact. The DEI folks weren’t fluent enough in how the systems actually worked. I saw a gap

What I had to push through was the imposter syndrome that comes with stepping into a space dominated by engineers and lawyers with very specific credentials. I don’t have a computer science degree or a law degree, but I have years of understanding how policy shapes people’s lives, and I’ve come to believe that’s exactly what’s missing from most AI governance conversations.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

All of it and not just in the ways I expected.

EEO and DEI work trained me to look at systems from the margins inward. That’s actually a sophisticated analytical lens, and it maps directly onto AI ethics. When I read about algorithmic bias or automated decision-making, I’m not encountering new ideas, I’m seeing old problems wearing new clothes.

The humanities background gave me something equally valuable: the ability to write about hard things in ways that don’t require a PhD to understand. A lot of AI policy writing is inaccessible by design, whether intentionally or not. I can bridge that gap.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I chose Substack because a good friend of mine suggested it to me, and she was right, it is a great platform for creating engaging collaborations and connections, like this one with you, Katharine. Thank you for asking me to join you in this interview.

I’m less than six months in, so I won’t pretend I’ve figured it all out. But what I’ve found is that Substack gives me something I didn’t have before: a record. A body of work that shows how I think and what I care about. A consistent body of writing builds trust.

Right now, it’s less about income and more about positioning. I’m building toward a career in AI safety and governance, and every piece I publish is part of making the case that I belong in that conversation.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My work is for people who care deeply about fairness and justice and who are starting to realize that AI is one of the most consequential equity issues of our time, but who feel locked out of the conversation because it’s too technical or too disconnected from lived experience.

It’s also for people inside the AI space but haven’t had the training to think about bias and systemic impact.

The problem I solve is the gap between values and systems. A lot of people know AI can be biased. Far fewer understand how, why, or what to actually do about it. I write to close that gap, to make AI ethics and governance legible to people who have every reason to care.

“What turned out to be harder than you expected when you started… and what was easier than you imagined?”

Harder: consistency, showing up regularly when you’re also holding down a full-time career and building something new. There are weeks when the ideas flow and weeks when you’re running on fumes and still trying to publish something worth reading.

Also harder: the silence in the beginning. You put something out that you worked hard on, something you genuinely believe matters, and sometimes it crickets. Learning to keep going anyway is its own kind of discipline.

Easier than I expected: finding my voice. I thought I’d spend months figuring out how to “sound” like an AI writer. What I found was that I already had a voice.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

I’m still early in it, so take this with that context in mind, but here’s what I’ve learned so far.

Write about what you actually think, not what you think people want to hear. The pieces I’ve been most nervous to publish have gotten the most response. Cite sources because it also shows the amount of research you did.

Don’t wait until you feel ready. I started before I felt qualified, before I had a big audience.

And engage, write collaborative articles, be part of the community, and build real connections. I have built at least ten connections in these last few months where we try to keep in touch and have talked outside the platform.

“What nearly made you quit, and what actually kept you going?”

The imposter syndrome is real and it doesn’t fully go away. There are moments, usually when I’m reading something written by a policy expert with decades of experience or a researcher with institutional backing, where I think, who am I to be writing about this?

What keeps me going is the response I get from readers who say they finally feel like they can understand this stuff. That they’ve been wanting to engage with AI ethics but everything they found felt either too technical or too disconnected from the real-world consequences they live with.

The more I write about AI policy and governance, the more I understand what I actually think, and the more certain I become that this is where I’m supposed to be headed.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Don’t wait for your background to feel like enough. The spaces that need changing most are usually the ones that haven’t made room for people like you yet.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

Right now, my portfolio is in active construction. I guess LinkedIn and Substack is where I’m building my public voice and my body of work in AI ethics.

For me, these two work together for networking and opportunity purposes, you never know who could reach out to you or vice versa.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

Deciding to start The Responsible AI Brief on Substack was quite the change for me and a lot of positive things have followed that, a lot more networking possibilities and hopefully more career opportunities.

Before I started writing, I had a lot of private conviction about where AI governance was going wrong. Now I am building a record of it, and that record could open doors.

What’s next is continuing to build toward AI policy and governance work in a more formal capacity. I want to be in the rooms where these decisions are being made, contributing the perspective that’s most often missing: one grounded in civil rights and equity.

I’m not fully there yet. But I’m further along than I was six months ago, and that’s enough to keep going.

Links & Resources

Connect with Christina…

On LinkedIn

The Responsible AI Brief

Weekly newsletter delivering AI ethics analysis and practical guidance for leaders, HR professionals, and concerned citizens.

By Cristina

Related Articles

Welcome to The Responsible AI Brief

10 Lessons From the EU AI Act That Every Country Should Consider (Before It’s Too Late)

What If Community Is the First Layer of AI Governance?

Read More

Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

This Career Pivot Playbook features Mantel Featherson, the writer behind FutureProof50, a Substack for professionals over 50 who want to turn what they know into income they control.

Mantel’s background is corporate change management. He spent over two decades inside some of the biggest names in the business, DuPont, Merck, SAP, and KPMG, helping organizations navigate the hardest part of any technology rollout. Not the systems. The people.

But when he was laid off at 55, most people with his background would have found another corporate job and moved on. Mantel saw it differently. What came next was not straightforward, but it led somewhere most professionals never think to go.

Today he runs a premium advisory program, is building a learning community, and publishes on Substack for an audience the business world largely ignores. Writing became the thread connecting his thinking, his framework, and the professionals who follow his work.

In this Playbook, Mantel talks about what two decades in corporate change management actually taught him about people, what the layoff at 55 really felt like, why he started writing in public, and how he built something most professionals in his position never think to try.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Mantel

Mantel Featherson spent over 20 years helping large organizations manage change. Then, at 55, the organization changed on him. A layoff in November 2023 launched him into a failed e-commerce business, a job search that went nowhere, and eventually a clarity that only comes from hitting a wall.

Today he is the founder of FutureProof50, author of Expert to $100K+, and creator of the Expert to $100K+ framework, helping professionals over 50 turn decades of earned expertise into income and independence. He holds a Doctorate in Human Resources Development from Drexel University and is based in Philadelphia, PA.

You can follow his work here →

Expert to $100k+

For 50+ professionals ready to own their expertise and build $100k+ income without a 9 to 5

By Mantel Featherson, EdD

Mantel reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I spent over 20 years in organizational change management, working with companies like DuPont, Merck, SAP, and KPMG. My work focused on the people side of technology change, specifically helping workers let go of familiar systems and adopt new enterprise software. Most people think technology implementations are IT projects. They are actually human performance projects, because getting a workforce to change how they work is where most of these initiatives succeed or fail, and that was my lane.

I genuinely enjoyed helping professionals navigate change. However, the corporate structure and politics that surrounded that work was another story.

In 2017, I was looking for a way out of the corporate world, I applied to the Doctor of Education program at Drexel University. My honest motivation was to enter academia. I thought a doctorate would open a door to a different kind of career, one built around research, teaching, and ideas rather than org charts and stakeholder management.

I graduated in 2021 with a Doctorate in Workforce Development. The experience at Drexel was valuable in ways I didn’t expect, but I came out realizing that a career in academia was not the answer I had been looking for either.

So I kept working in the corporate world, with my doctorate, and still searching for something new. In November 2023, at the age of 55, the decision was made for me. I was laid off from my last corporate job.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

After the layoff, I did what most people in my position do. I updated my resume and started looking for a new corporate job. But I was going through the motions, I didn’t want another job. I just didn’t know what else to do.

So while the job search dragged on, I decided to launch an e-commerce business selling fitness and wellness products to the 50+ market. I set up a Shopify store, sourced products, and started writing blog posts. I also hired a marketing agency to help grow the business. Six months later, I had spent over $5,000 in marketing and hundreds of hours of effort. Total revenue: zero dollars. I shut it down.

That failure stung. But it also sparked something. It showed me I wanted to build something of my own. I just hadn’t found the right thing yet.

The clarity came from LinkedIn. I started noticing that posts about ageism and AI displacement were generating enormous engagement. Whenever someone wrote honestly about those topics, the comments flooded in, mostly from professionals over 50 who were frustrated, scared, and feeling invisible.

They were worried about finding work, about retirement, and about staying relevant in an economy that seemed determined to move past them. Reading those comments, I kept thinking: these are my thoughts. This is exactly what I have been feeling.

That recognition became the business. In August 2025, I created Expert to $100K+, a concept and framework designed to help professionals over 50 leverage their most valuable asset, decades of earned expertise, to build impact, income, and independence from the traditional 9 to 5.

The pivot for me was the realization that the problem I was qualified to solve was the one I had been living.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

The skill I least expected to matter was my ability to design learning experiences. In the corporate world, that meant building onboarding programs, training curricula, and leadership development programs.

Outside of it, that same skill became the foundation of the book (Expert to $100k+) my forthcoming course, advisory programs, and the frameworks I create for my 50+ professional audience. I understand how adults actually learn. I know what makes people act on new information instead of filing it away and forgetting it.

That is not a common skill among content creators, and it shows in the quality of what I build.

Change management turned out to be an even bigger advantage than I anticipated. My entire career was spent helping people navigate uncertainty, resistance, and fear of the unknown. My audience lives in that space every day.

They are smart, accomplished professionals who have been told, directly or indirectly, that their best years are behind them. I know how to meet people there and help them move forward. That is not something you learn from a course. It comes from years of sitting in rooms with people who are scared and helping them find a way through.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I chose Substack because it rewards depth over virality. My audience is not scrolling for quick entertainment. They are professionals in their 50s who have been burned by shallow advice and empty promises, and they need substance they can actually use.

Substack lets me build a body of work that compounds over time, own my direct relationship with readers, and monetize without being at the mercy of algorithm changes or platform decisions made by people who have never thought about this audience.

It is one part of a larger ecosystem that includes a book, community, advisory, and digital products, but it functions as the trust-building engine for everything else. The newsletter is where people get to know me.

Everything else flows from that relationship.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My work is for professionals over 50 who are good at what they do but quietly terrified that it no longer matters.

Many of them have been laid off, pushed out, or sidelined. They are staring at the next 15 to 20 years wondering what comes next, whether they have enough saved, whether anyone will hire them again, and whether the career they built still means anything.

The problem I solve is specific. There is a gap between having deep expertise and knowing how to turn that expertise into income outside of a 9 to 5 job. Most people in my audience have never thought of themselves as an expert in the entrepreneurial sense.

They have thought of themselves as an employee, a professional, a title on an org chart. I help them see what they already have, show them how to structure it, and give them a path to build something that pays them for what they know rather than what role they currently occupy in a company.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

Launching was harder than I expected. It was the silence at the beginning. You build something you genuinely believe in, you put it out into the world, and the response is crickets.

That tests you in ways that a corporate job never does, because there is no manager or performance review telling you that you are on the right track. You are operating entirely on conviction, and some days that is not enough to quiet the doubt.

The failed e-commerce business made that silence even louder. I had already lost $5,000 six months before I found the right direction. Starting over with Expert to $100K+ meant I was also carrying the weight of that earlier failure.

What was easier than I expected was the resonance once I found my voice. When I stopped writing like an academic and started writing like someone who had actually lived the experience I was describing, people responded immediately. The audience is out there. They are hungry for someone who understands them. They just need to hear from a real person, not a polished personal development brand.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

The journey has been a slow build that is starting to compound, which is exactly what I was told to expect and somehow still surprised me when I experienced it firsthand.

My advice comes down to three things.

First, commit to writing for a specific person with a specific problem. A newsletter for everyone is a newsletter for no one. The more precisely you can describe the person you are writing for, the more that person will feel like you are speaking directly to them, because you are.

Second, write from your real experience rather than from research or theory. Your lived story is your competitive advantage. There are thousands of people writing about career transitions. There is only one person who has lived yours.

Third, treat your free content like something you are proud of. The people who eventually pay for your work are almost always people who were first floored by something you gave away.

“What nearly made you quit, and what actually kept you going?”

Looking at creators with tens of thousands of subscribers and asking myself what I was doing wrong, whether I had started too late, whether the market was already too crowded. That kind of thinking is corrosive and it crept in more often than I would like to admit.

What kept me going was the quality of the audience I was building even when the numbers were small. When a 57-year-old former HR director writes to tell you that something you wrote made her believe she was not too late, you cannot walk away from that.

The mission stayed larger than the metrics on the days when the metrics were not on my side.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Stop waiting until you are ready.

You have been getting ready for 20 years. The expertise is already there. What is missing is not more preparation or credentials or a better plan. What is missing is a decision to stop treating everything you know as something that only counts inside a job description.

Start by solving one specific problem for one specific person. Do it so well that they tell someone else. Do not try to build a platform, a brand, a business, and a product all at once. Pick the person. Solve the problem. Prove it works. Everything else gets easier after that.

And if your first attempt fails, as mine did, let it teach you something before you let it stop you. The e-commerce business I shut down after six months of zero sales was not a detour. It was the first chapter in a story that is still being written.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

Expert to $100k+ on Substack is a central part of the ecosystem that I’m building, which also includes my website (https://futureproof50.com).

Beyond that, I am also launching a learning community and work with individuals through my premium advisory program.

I have developed the Expert to $100K+ framework and book, and I am building out a suite of digital products designed to give professionals a repeatable process for monetizing what they know.

I am also developing functional nutrition products specifically formulated for cognitive performance in the 50+ market, which speaks directly to the audience I serve.

These are not separate businesses running in parallel. They feed each other. A Substack reader becomes a student. A student becomes an advisory client. A client’s transformation becomes the next piece of content. The goal is an ecosystem where every entry point leads someone deeper into the work so they build income, impact and independence on their terms.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

The most important decision I made so far was choosing to de-prioritise finding a job.

I knew I couldn’t re-enter a system that had already signaled I was expendable, so I started betting on the one thing no company could take away: my expertise. .

The road between that decision and where I am now was not straight. There was a failed business, a long job search that went nowhere, and more than a few months of genuine uncertainty.

But each of those experiences sharpened my understanding of exactly what my audience goes through, which made everything I build for them more real and more useful.

Looking forward, I am building FutureProof50 into the leading platform for professionals over 50 who are done waiting for permission to build something of their own. The audience is massive, deeply underserved, and ready for something different. I’m excited to serve this audience.

Links & Resources

Connect with Mantel →

Website: www.futureproof50.com

LinkedIn: linkedin.com/in/mantelfeatherson

Expert to $100k+ book : https://futureproof50.com/pages/expertto100k

Expert to $100k+

For 50+ professionals ready to own their expertise and build $100k+ income without a 9 to 5

By Mantel Featherson, EdD

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Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

This Career Pivot Playbook features John Brewton, the writer behind Operating, a Substack about the history and future of running companies, and what it takes to build and lead one in the AI-first economy.

John’s background is operator-first. He grew up inside a family business and after attending Harvard and the University of Chicago, he went back to the fold to help his family to grow and eventually sell their business.

But it is what came after this huge exit is where his story it gets even more interesting.

He didn’t slow down. He didn’t stop working… He made a decision that most people with his experience never seriously consider, and it changed the shape of his career entirely.

Today he runs a strategic advisory firm, leads a paid founder community, and publishes daily on Substack. Writing became the thread connecting his thinking, his consulting, and the operators and builders who follow his work.

In this Playbook, John talks about what two decades of running a real business actually can teach you, what the exit really felt like, why he started writing in public… and how he built a second career that most operators never think to try.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About John

John Brewton is the Founder & Managing Director of 6A East Partners, a strategic advisory firm, and the creator of Operating by John Brewton, a bestselling Substack newsletter with +5,000 subscribers and +60,000 followers across social platforms.

A Harvard-trained economist with 20+ years of operating experience, John scaled and exited a $75 million family business before building one of Substack’s fastest-growing publications on business strategy, economics, and the AI-first economy.

He writes for the people who actually run things. He writes for builders.

You can follow his work here →

Operating by John Brewton

Weekly Reporting on the History & Future of Operating Companies

John reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I grew up inside a family business. R.G. Brewton was a B2B industrial distribution company my family built from scratch (warehouses, forklifts, Fortune 500 contracts, manufacturing plants, the whole operation). Dinner table conversations were about margins and logistics before I knew what either word meant.

Out of high school, oddly, I chased a rockstar dream as a drummer for a few years, before becoming very tired of working four jobs to get by and deciding to head to college. I began my college career at the Commnity College of Allegheny County, before transferring to the Honors College at the University of Pittsburgh and then to Harvard. I went to Harvard to study economics, then started PhD work at the University of Chicago. I loved the intellectual rigor, but I kept getting pulled back toward the practical side, how do companies actually work? What separates those that survive from most fail? Eventually I chose the family business over the academic track, on the advice a professor. The plan was actually to take one year to help my folks sell the company after I had finished all of my phd coursework and research.

One year became 13. I started work at the ground level as a Sourcing Specialist, then as an Operations Analyst, implemented our first ERP system, automated hundreds of hours of manual work, earned my way into the Director of Operating position after four years of work, and eventually took over as CEO.

Over the next five years, we scaled from $42 million to $75 million in revenue. We improved EBITDA by over 300%. We managed Fortune 500 relationships with companies like Boeing, Tesla, Harley Davidson, General Motors, and Johnson Controls. We built international operations in Mexico and Costa Rica. And in August 2021, we completed a successful exit and sale of the business. Our COVID story could be a book, but that one will have to wait for another time.

After the sale, I founded 6A East Partners, my strategic advisory firm, and started writing. That writing became Operating by John Brewton on Substack, and it’s become the centre of everything I do now.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

When you sell a company your family built, you don’t just lose a business. You lose an identity. For thirteen years, the answer to “what do you do?” was obvious. After the exit, it wasn’t.

I started consulting, which felt natural. But I noticed something: the most impactful conversations I was having weren’t behind closed doors with a single client. They were the frameworks and lessons I was writing down for myself, things I’d learned the hard way about running a P&L, managing people, making decisions under uncertainty. I realised that if I published those ideas, I could reach thousands of operators who needed the same clarity but didn’t have a $500-an-hour advisor.

What I had to push through was the voice in my head that said operators don’t write newsletters. Operators run things. But the truth is, writing is operating, it’s just public. And once I committed to publishing every single day, everything changed.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

Three things, and none of them are what people expect.

First, economics training. My background in behavioural economics and market dynamics gives me a lens that most business thinkers don’t start from. The analytical and mathematical rigor that has come from that training is invaluable each and every week of my working life.

Second, operational discipline. Running a 100-person company taught me systems thinking. I don’t just write article and advise my client, I build operations around how my strategic thinking and content is produced and applied. I track every post and every client’s performance in spreadsheets. I run weekly forensic reviews on what worked and what didn’t for me and my client. I treat my very singular work as a company, because it is one.

Third, being an introvert. I know that sounds counterintuitive for someone building a public brand, but deep focus is a superpower, as is the capacity to listen intently, absorb negative feedback without anxiety and calmly see the bigger pciture.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I’m everywhere, but strategically. LinkedIn is my top-of-funnel, it’s where I reach operators, founders, and executives with 7-10 posts per week. That’s where I built my audience from under 0 to over 30,000 followers in about a year. Substack is my intellectual home base. It’s my heart. I publish seven articles a week on Substack across several formats: long-form operating essays, company case studies, my weekly “Operating Week Ahead” briefing for busy folks, and practical frameworks that translate big ideas into small-team execution.

The system is designed as a funnel: free content on social creates awareness, free Substack content builds trust, paid subscriptions deepen the relationship, and the Operating Founder membership creates a community of serious builders who eventually become consulting clients. Every piece of content works to serve that ladder. It’s deifnitely a work in progress, but I’m happy with where things are.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

I write for operators, builders, founders and creators of one person businesses, small businesses and family businesses.

The problem I solve is this: Strategy is critically important and super fun to develop. But disciplined, consistent execution is always and forever the variable. The tools are changing fast, AI is rewriting the playbook for how work gets done, but the need for clarity, structure, and good judgement only grows. Most business content is theory dressed as insight. I give people frameworks they can actually use, grounded in 200 years of management practice and the newest signals from markets. Think of it as an operating manual for the AI-first economy.

“What turned out to be harder than you expected when you started — and what was easier than you imagined?”

Harder: The sheer volume required to break through. There’s no shortcut to earning an audience’s attention. I committed to daily publishing and it took months before the compounding kicked in. It’s lonely work, especially in the early days when you’re writing into what feels like silence. If I had known how much work all of this would take when I started two years ago, I doubt I would have persisted.

Easier: Having something authentic to say. That sounds simple, but it’s the biggest advantage of pivoting after a full career rather than starting from scratch. Twenty years of work gave me a library of experiences to draw from. I never have to wonder what to write about. I have more ideas than I have hours. That endless reservoir of creativity is also how I know I’m doing the right work.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

Substack has been transformative for me. I love the community, curiosity, and kindness across the platform.

My advice: treat your newsletter like a business, not a blog. Track your numbers religiously. Know your open rates, your click-through rates, and your conversion from free to paid. Run a weekly forensic on your content, what performed, what didn’t, and why. Build relationships with other writers through Notes and cross-promotion. And above all, publish consistently. Consistency compounds. I write every single day, and that discipline is the single biggest driver of my growth.

“What nearly made you quit, and what actually kept you going?”

The identity crisis after selling the family business nearly broke me. When you’ve operated a company your whole adult life and suddenly that’s gone, you don’t just lose a job, you lose the structure that tells you who you are every morning.

There were months where I had no idea what to do next, and I wasn’t sure any of this would work over the last two years. But I knew I loved making the content and was making wonderful new friends.

What kept me going was the response from readers. What kept me going was the new relationships. Scalability is overrated. Moving one person forward matters more than a thousand likes. I genuinely believe that, and it’s what gets me up at 4 AM to write.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Your experience is the asset. Your humanity is the asset. Your eccentricity is the asset. You are the asset. Stop undervaluing what you know. You have a library of insights that other people will pay to access. The world doesn’t need more generic content. It needs your specific perspective, delivered with honesty and discipline.

Start writing before you feel ready. Publish before it’s perfect. Build the plane while you fly it. And design your content as a system, not a series of one-offs. Every post should serve a purpose: build trust, demonstrate expertise, or deepen a relationship. If it doesn’t do one of those three things, don’t publish it.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

My portfolio has four engines working together. 6A East Partners is my strategic advisory practice, working with larger companies and growth-stage businesses on AI transformation, operational strategy, and financial performance. Operating by John Brewton is my Substack newsletter with free and paid tiers, plus the Operating Founder membership—a $99/year program that sold out 100 seats in two weeks and now includes weekly live cohort sessions with serious founders building real businesses. I also build across LinkedIn, X, TikTok, and Facebook, and am working to make each serve a different segment of the discovery process for my work.

They all feed each other. Social creates reach. The newsletter creates depth and trust. The paid membership creates community. One Substack article becomes 14 LinkedIn posts, multiple social clips, and a library of reusable frameworks. The system is designed so that no single piece of content dies after one use. I have enough content in my Canva libraries and on my computer to post multiple times a day for the next two years.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

The decision to publish every day. Everything follows from that. Daily publishing forced me to develop systems, build discipline, sharpen my thinking, and treat my writing like the business it is. It’s the operating principle behind everything I’ve built since the exit.

What’s next: I’m building Operating into the go-to resource for people building businesses for the first time, people pivoting their careers in an entrepreneurial direction. I’m expanding the Operating Founder community, developing more comprehensive resource libraries and downloadable tools, and continuing to document everything I’m learning in real time. I’ll also be launching a Skool comunity for the Founders program in the week’s ahead.

The long-term vision is to build something that helps the next generation of operators and businesses think more clearly, execute more effectively, and build lasting companies.

Links & Resources

Connect with John →

Website: operatingbyjohnbrewton.com

LinkedIn: linkedin.com/in/johnbrewton

Operating by John Brewton

Weekly Reporting on the History & Future of Operating Companies

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Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

He started in entrepreneurship and never left.

Over the years, he built companies across sales consulting, coworking, workplace strategy, and real estate development. He questioned standard answers and built alternatives when they did not make sense.

Eventually, he saw that the real asset was not the companies. It was the skill set.

Solving problems with limited time and money. Making decisions without full information. Staying steady under pressure. Creating structure where there is none.

The shift was not a reinvention. It was an expansion.

Entrepreneurship evolved into fractional COO work. Clear priorities. Better systems. Fewer operational fires. At the same time, he began writing about energy management for knowledge workers facing constant cognitive load.

Today, he runs a portfolio career across advisory work, writing, and digital products. His Substack supports that system. It sharpens his thinking. It builds trust. It compounds over time.

In this Playbook, Dennis breaks down the moment he knew it was time to diversify, why audience growth does not equal income, how he chooses platforms, and what nearly made him quit.

He also shares the decision that set his direction early and the filter he now uses before committing to any new path.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

About Dennis

Dennis Hedenskog is the writer behind his Substack, The New Habits Newsletter, where he explores energy management, modern work, and operational clarity.

He is an entrepreneur, fractional COO, and former founder across sales consulting, coworking, workplace strategy, and real estate development who built his career by questioning the status quo and creating his own structure.

Today, he blends operational execution, entrepreneurial experience, and energy management to help founders run better businesses and help knowledge workers manage the demands of modern work.

You can follow his work here →

The New Habits Newsletter

For people learning to work with their energy — not against it — while modern work keeps asking for more.

By Dennis Hedenskog

Dennis reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

As a professional, my life has been all about entrepreneurship. A mix of rebelliousness and inability to accept solutions that don’t make sense to me has led me to launch businesses across sales consulting, coworking, workplace strategy, and real estate development.

The experiences from entrepreneurship and distaste for the status quo have led me to where I am today: running a Fractional COO business and a content creation business aimed at helping knowledge workers with energy management.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

I’m a curious person with an interest in several things, and I wanted to have a professional life where I could explore different topics and make use of my experience in various fields.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

Solving problems with too little time and money. This is basically what entrepreneurs have to do, and this has helped me act with calm and confidence in my business life, and it’s still my edge and source of momentum.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

Substack is my main platform today, and for one simple reason, it’s the one that makes me feel the best when I use it. My relationship with social media has been complicated over the years, and my guiding principle for choosing a platform is what Tim Ferris says “if my body doesn’t say hell yes, then it’s a hell no”. I go with that, rather than focusing on the ability to earn money.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

I help entrepreneurs solve everyday challenges with improved structure through my fractional COO business, and I help knowledge workers deal with the demands of modern work by teaching energy management.

“What turned out to be harder than you expected when you started… and what was easier than you imagined?”

Growing an audience has been easier than expected, but I’m learning that vanity metrics (like your following) doesn’t necessarily translate into earnings. So packaging, communicating, and earning the trust of your followers is the biggest challenge.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

I’m surprised over how much I like the people on Substack. I feel that the experience is genuine and more honest than on other platforms. And my advice for others is to be honest about what value their life experiences can give others and learn how to translate that into actual learning for others.

Also, I’d like to encourage people to share their actual experiences and not get lost in the “here’s how you grow and make money on whatever platform” advice (which the internet is saturated with). I believe there’s still room for creating art online.

“What nearly made you quit, and what actually kept you going?”

Brushing up against the trade of how much of your time and value you are investing versus what reciprocal monetary exchange is taking place. The trade is still worth it (even though some days I wonder if that’s actually the case 🙂).

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Focus on understanding what problem you can solve for your potential customers is number one. Spend more time understanding that than you think. Once you get that, you can start playing with the how (platform, packing, delivery etc). Don’t skip the basics.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

I leverage LinkedIn for my fractional COO business. I use that mostly for networking and building relationships.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

The decision to found my first company was a fork in the road, and for me going back was never an option. Moving forward, I’m looking forward to being of service for my clients, audience, and customers.

Links & Resources

Connect with Dennis…

The New Habits Newsletter

For people learning to work with their energy — not against it — while modern work keeps asking for more.

By Dennis Hedenskog

www.dennishedenskog.com

→ The 14 Day Energy Reset

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Behind the Pivot

Learn how to turn your current skills and experience into income and build a portfolio career beyond a single job, so you’re more resilient and in control.

The Career Pivot Archive

Real-world career pivots, portfolio paths, and practical lessons from some of your favourite Substackers you can apply to your own next move.

Career Questions Answered

Practical, strategic answers to the career questions ambitious professionals are asking as work, security, and opportunity continue to change.

I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

❤️ Loved it? Restack 🔁 and share ✅

🤔Is there a question you wish had been asked?
Drop it in the comments, and let’s keep the conversation going.

She began in pediatric oncology, then moved into flight medicine, transporting critically ill patients and making high-stakes decisions mid-air.

Over time, she started exploring other fields. Markets. Macroeconomics. Writing. She realized the skills she had built in medicine did not belong to one industry. They could be applied elsewhere.

Emotional regulation. Pattern recognition. Decision-making under uncertainty. Clear communication under pressure.

Her shift was not dramatic. It was layered. Curiosity turned into disciplined study. Study turned into consistent action. Writing became infrastructure, not expression.

Today, she operates at the intersection of nervous system regulation, macro markets, and capital allocation. Her Substack is not a side project. It is an asset built to compound.

In this Playbook, Jessica shares how clinical precision translated into market discipline, how she moved through identity friction, and why building for decades changes how you think about income, risk, and control.

✨About Career Pivot Playbooks

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

Join free to get the Skill-to-Income Discovery Tool and uncover practical ways to turn your existing skills into income.

About Jessica

Jessica is the writer behind NP Fellow, a newsletter about health, markets, and disciplined thinking.

She is a Substack bestseller, nurse practitioner, stock trader, and former pediatric hematology oncology and flight nurse who rebuilt her career around sovereignty.

Today, she blends healthcare, nervous system science, macro market analysis, and writing to help others think clearly, build financial literacy, empower people to become the CEO of their health, and design work on their own terms.

You can follow her work here →

NP Fellow Become the CEO of Your Health

Weekly training for emotional adulthood: the psychological skills most adults were never taught.

By Jessica Drapluk

Jessica reflects:

“Can you share a bit about your professional background and the path that led you to where you are today?”

I began my career in pediatric hematology oncology nursing, where I spent five years caring for children and families navigating life-threatening diagnoses. After that, I worked four years in flight medicine, transporting critically ill patients and making high-stakes decisions mid-air.

Healthcare trained my nervous system. In oncology and flight medicine, clarity under pressure isn’t optional. You learn to regulate emotion, assess incomplete information quickly, and act decisively.

However, sitting with families whose lives changed overnight also shifted how I viewed stability. When you witness that kind of uncertainty regularly, you start thinking differently about time, income, and control.

That awareness expanded beyond medicine. I began to see fragility in professional identity and income structures. Depending on one employer or one title felt increasingly narrow.

At the same time, I had always been drawn to markets and writing. What started as curiosity became discipline. I studied macroeconomics, trading psychology, and capital allocation seriously. I also immersed myself in functional medicine and mental health, initially to optimize my own health, then to empower others.

NP Fellow became the intersection of health, wealth, and disciplined thinking mixed together.

“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”

There wasn’t one dramatic turning point. It was a slow realization that I didn’t want to rely on a single structure for income or identity.

Working in high-acuity medicine made uncertainty normal. I didn’t fear volatility, but I wanted leverage and ownership. I wanted skills that compounded beyond a salary.

The hardest part wasn’t learning markets or writing publicly. It was pushing through identity friction. Expanding beyond “nurse practitioner” into markets and publishing felt vulnerable.

What helped was recognizing that healthcare, markets, and mindset are all systems. I wasn’t abandoning one world. I was translating skill sets into a broader arena.

“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”

Pediatric oncology and flight nursing prepared me for markets in unexpected ways.

Both require emotional regulation under pressure. Both demand pattern recognition and disciplined decision-making with incomplete data.

Trading is not just analytical; it’s psychological. If your nervous system isn’t regulated, your execution won’t be either.

Healthcare also trained me to translate complexity into clarity. Whether I’m explaining dopamine regulation or sector rotation, the goal is the same: simplify without diluting.

“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”

I chose Substack intentionally. I didn’t want to build inside algorithm volatility. I wanted ownership, depth, and longevity.

Substack allows me to build intellectual assets; not just posts. Through NP Fellow, I write about nervous system regulation, resilience, and functional medicine. Alongside that, I share macro market analysis, asset class tracking, trade ideas, and disciplined capital allocation strategies.

The platform supports long-form, thoughtful work. It’s part of my income mix, but more importantly, it’s my long-term intellectual infrastructure.

“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”

My work is for people who want sovereignty, freedom, and absolute personal power.

People who want to think clearly in volatility.
People who want financial literacy instead of financial fear.
People who want to optimize their health instead of outsourcing it.

The problem I solve is fragmentation. Many people treat health, money, and mindset as separate. I help them see the connection. Internal regulation strengthens external decision-making. And disciplined decisions compound over time.

“What turned out to be harder than you expected when you started… and what was easier than you imagined?”

Harder than expected: consistency without immediate validation. Writing weekly. Studying markets daily. Publishing publicly. Staying steady when growth is nonlinear.

Easier than expected: connection. When you write honestly and clearly, people respond. Substack readers appreciate depth and frameworks over noise.

The biggest lesson? Compounding requires patience.

“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”

My journey on Substack has been deeply positive. It rewards thoughtfulness and attracts readers who value long-term thinking.

My advice: write timeless work. Don’t chase trends. Build frameworks that will still be useful in five years. Focus on clarity and consistency over virality.

And own your audience. Build an asset, not dependency.

“What nearly made you quit, and what actually kept you going?”

There were moments when it would have been easier to retreat to one professional identity. Markets are volatile. Writing is exposed. Income isn’t always linear.

What kept me going was perspective. Oncology teaches you what truly matters. Flight medicine teaches composure. Markets teach patience.

Volatility is structure; not failure.

“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”

Learn evergreen skills and multiple high-income skills. Layer your skills intentionally. Don’t abandon your foundation, build on top of it.

Learn how money works. Understand markets. Develop diversified income streams.

But equally important: build internal capacity. If your nervous system collapses under uncertainty, diversification won’t feel empowering.

Future-proofing is both internal and external.

“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”

My portfolio includes nurse practitioner expertise, pediatric oncology and flight experience, functional medicine education, Substack publications, paid digital products, active trading, and macro market education.

Each layer reinforces the others. Health strengthens clarity. Clarity strengthens capital allocation. Capital allocation strengthens optionality. I’m not building for trends. I’m building for decades.

“Looking back, what’s one decision that changed everything… and what’s next for you?”

One decision changed everything: choosing to build assets instead of outputs.

When I took markets seriously, I understood compounding in a new way. Capital compounds when allocated wisely. Ideas compound when structured intentionally.

NP Fellow is becoming a timeless content and asset-generating machine — an archive on health, wealth, and disciplined thinking that readers can return to for years.

Next, I’m focused on expanding that infrastructure. Deepening the frameworks. Growing the intellectual library. Allocating capital strategically with a long-term vision toward philanthropy.

Markets change. Systems shift. Disciplined thinking and emotional regulation are timeless. That’s the foundation I’m building on.

Links & Resources

Connect with Jessica…

NP Fellow Become the CEO of Your Health

Weekly training for emotional adulthood: the psychological skills most adults were never taught.

By Jessica Drapluk

NP Fellow Collective Spotify link:

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I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.

🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.

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