This Career Pivot Playbook features Derek Hughes, the writer behind the Irresistible Writer, a Substack built for people who want to grow an audience and get paid doing it.
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 →
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:
Daily Notes (for discovery)
Recommendations (for compounding growth)
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
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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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Very encouraging.