This Career Pivot Playbook features James Presbitero, the writer behind Unpromptable, a Substack about staying irreplaceable in the age of AI, and what it takes to build a business around your voice when the tools are coming for your craft.
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 →
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/
Related Articles
Unpromptability: 5 Steps To Become Irreplaceable in the Age of AI
5 AI Systems Nobody’s Talking About (That Actually Build Moats)
The Only Moat Left In The AI Age
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.
Thank you for letting me share my story, Katharine! These questions were super interesting.
I don’t know if I like @James Presbitero’s smile or your smooth new thumbnail layout more. :)