Most of us who work for ourselves aren’t one clean thing—we’re cartoonists who also teach, consultants who also write, coaches who also run the whole business. And after a couple decades of that, you can end up with an enormous body of work that almost nobody can actually see, least of all the AI tools now deciding who you are. To talk through what to do with a career’s worth of ideas, we’re bringing on Meg’s friend, colleague, and client, Jessica Abel.

Jessica is a cartoonist and author turned business coach for professional creatives, helping them finish the self-generated work that has no deadline and get paid well enough to actually have time for it. In this episode, she walks us through the very unglamorous process of taking 10-plus years of courses, newsletters, and frameworks, most of it locked behind paywalls or buried in podcast audio, and making it cohesive and legible for both people and AI. She and Meg get honest about why podcasting is great for ideas and terrible for discoverability, what it actually takes to update a Wikipedia page, and why The Guardian counts as proof but a marketing podcast doesn’t.

We talk about the difference between productivity and capacity, why “decide” and “reflect” are the phases everyone skips, and what it means to pay yourself first with your time instead of your leftover minutes. We get into cyclical burnout, idea debt, and the genuinely hard work of deciding what you’re not going to do—and being at peace with it.

* Why “multi-hyphenate” isn’t a bug of entrepreneurial life

* Cyclical burnout: what happens to someone who always has new ideas

* How Jessica consolidated a career-long body of work into something legible using a bottom-up, feedback-driven process (and Claude)

* Capacity as a lens—not just your time, but your neurological and emotional bandwidth—and why it fluctuates by the day and the season

* Grow work vs. build work, and the tension between expanding your audience and cementing a legacy

* What it actually takes to be legible online—AI discoverability, entity confusion, and why Jessica still shows up as a cartoonist first

* The Creative Engine’s four phases—collect, decide, act, reflect—and why decide and reflect get skipped even though they’re the shortest

* The “flexible container”: building a finishing structure with edges that can still absorb a sick kid or a health flare-up

“I actually hate the word productivity and try to not talk about myself as a productivity coach, because—I still have to use it a lot ’cause it’s the word people know. But productivity literally means: how do you have the same amount of capacity and jam more stuff into it? How do you get more stuff out of whatever you have available? And of course you can look at it different ways, but that’s literally what it means in the economic sphere. Which is just a point of view that doesn’t work for humans, and especially creatives and people who have big ideas and are trying to do the self-generated stuff.” —Jessica Abel

About our Guest

Jessica Abel

Out on the Wire

In the Weights

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Meg Casebolt

Jessica Lackey

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