Nov 10, 2026   5 mins read

Illegible careers, shifting economies, and starting anyway

Plus: a 9x price gap inside one niche, and a designer's question about AI.

I used to be able to describe my job in one sentence. Now I can’t, and neither can most people I talk to — creator economy or not.

Kevan Lee, founder of Bonfire, wrote “Oops, I became an expert in a thing that no longer exists” a few weeks ago and it struck a chord for me. He spent his early career writing 2,000-word blog posts from scratch (same as me) — a skill that still exists, but isn’t as in-demand as it once was, because the job changed shape underneath him.

 
This is the same thing I’ve seen, just in the past 2-3 years:

• Content marketing turned into SEO
• SEO turned into GEO and AEO
• GEO and AEO turned into content engineering
• Content engineers leaned into PR
• PR people are now being asked to support with LLM citations

TLDR: we’re all chasing business clout, recommendations, and word-of-mouth through whatever channel search prefers at the time, and giving ourselves a title that pseudo-fits. What I liked about his piece is his conclusion: 

In his case, that’s:  

• Keep the behavior, ditch the role. Skills are what you do and behaviors are how you do it. He doesn’t use traditional SEO or 2020s-era org design anymore, but the curiosity, the deadline habit and the knack for figuring out hard things came with him.
• Learn something because it interests you. You can’t predict which tool is next, so skip the scramble. Pick skills for fun, and if one turns out useful later, that’s a bonus.
• Keep your taste. He doesn’t write 2,000-word posts anymore, but he still knows a good one when he sees it and can spot a flimsy argument. Tools and mediums change, and taste translates.

Same week, creator Justin Welsh wrote about a friend of his named Carol who wanted a 10-year plan for her career. He used to want that, too. Corporate life is awesome at getting folks to believe there’s predictability in it. But once he quit his job to become an entrepreneur, he never knew what decision would pay off. He just knew he learned from each one:

• Healthcare consulting taught him what people would pay for.
• Writing online taught him people wanted social media advice.
• That taught him to build courses.
• Now, he’s a multimillionaire living the “four-hour workweek” dream that so many of us hope for.

Which made me think about the shift that’s happening in the world at large right now, with AI, automation, etc. I think about this constantly when it comes to the people building on Circle.

And, as a marketer, let me predictably bring you to a Google Trends graph (or two), pairing an older idea or concept, next to a new career built on top of it.

Newsletters never went away. Searches for the word peaked back in 2004 and have bumped along since. Newsletter creators barely registered until mid-2025, then went vertical.

Community is as old as humanity itself. Searches for the word slid for 17 years and only really turned up in 2025. Community businesses sat near the floor until mid-2025.

Social media climbed steadily from about 2009. Influencers climbed for a decade, then—BAM—roughly doubled in 2025.

These are brand new careers, businesses, and needs that society is evolving into, whether due to economic strain, technological innovation, or shifting trust. You can’t plan for them. You can only take hold of the moment.

Justin’s story (which he can make sense of only looking backwards) is the pattern, but it’s not a playbook. Healthcare consulting, writing, and courses looks like a straight line now, but back then, it looked like three random jobs. Not a ten-year plan. Not a perfectly positioned niche. A pile of small decisions, little tests, each one showing him what the next one should be.

So I’ve swapped my question. Instead of “what’s my five-year plan?” I’m asking “what am I already good at that survives when the job description changes?” And then a smaller one: what’s the next thing I can try this month?

The name I’m giving it is the hindsight career. You don’t have to be able to explain it yet. You just have to keep track of what each thing taught you, so when the pattern finally shows up, you can see it.

The data desk: profitable coaching niches

Three years ago, nobody would have put "AI coach" on a list of coaching niches (nevermind profitable ones?!). Now, it has deep demand across all industries. We pulled coaching prices from about 70k+ paywalls, and the new map looks like this:

• Same niche, 9x gap. Business & marketing is the deepest coaching market on Circle: 1,105 group programs with a $1,500 median. The top tenth cost $13,854 or more.
• The new stuff already has a price. AI & tech, the closest category to AI-adoption coaching, has a $1,225 group median across 256 paywalls.
• The range is wide, but the middle is crowded. Real estate tops group coaching at $5,000. Parenting & family sits at $564. Fourteen of the 18 niches with enough data land between $1,000 and $2,500.

What explains the gap inside one niche is the buyer: whether they have the budget and the authority to say yes.

🤫 Steal this: before you pick (or rename) your niche, find out who controls the budget for the problem. In the International Coaching Federation's 2023 study, 57% of coaching clients were sponsored, meaning someone other than the client paid.

The full breakdown, plus how to test a niche before you build one, is on the blog.

One question I’m sitting with

At a recent event, Madison, our events pro, heard a graphic designer say out loud what plenty of people are thinking, and partially what kicked off my thinking for the essay above:

Anyone can make anything with AI now — so what makes you special?

Nobody had a tidy answer, but most people there agreed that non-scalable assets were the things to invest in:

• the community around your work (including those you bring together in-person)
• your taste, brand, and authority, built over years of experience and showing up
• your members’ and customers’ real words

Graphic design isn’t going anywhere. But it’s certainly changed. Sound familiar?

Coming up: every membership pitch sells recurring revenue. None of them mention the recurring work. (I’m about to ruin a few pitch decks.)

What's the strangest turn your career has taken that only makes sense now? Hit reply. I read every response.