notessamuele onelia

30 Jobs Through His 20s

The Story

Before his ADHD diagnosis at 36, Jesse Anderson had a career trajectory he could not explain to himself. “I did a few years of community college. Never got a degree or anything. And then through my twenties, I probably have like 30, 30 different jobs. I was jumping all over the place.” (Source 1).

The pattern repeated. “Whenever I would get a job, and I’d love it at first. And I’d be a great employee. And, yeah, my bosses would usually love me when I first started and I’d do all the stuff. And then over time I would either get bored of the job. Or, you know, I would start forgetting details. like important things I was supposed to do would kind of like fall out of my brain. And then I would just, never, ever remember to do that thing again.” (Source 1).

In school the same dynamic showed up earlier: “in school I had extreme difficulty turning things in on time. Uh, homework at one point in junior high, I basically just stopped doing homework all together… I just couldn’t stay. Focused.” (Source 1).

He tested well, which masked the problem. “Luckily for me, I tested really well… So the homework was a real big, obvious thing… but because I tested well, I kind of, flew under the radar, as it were like, I was getting Bs and Cs.” (Source 1). Teachers landed on the same line: “You’re not reaching your potential. You could do so much more if you just tried, if you just tried harder or cared a little bit more.” (Source 1).

His self-explanation at the time: “I just felt I was broken somehow and didn’t know how else to explain it.” (Source 1). The pattern only became legible in retrospect: “I talked about this earlier, like this commonly, when I had that feeling, it often meant like, this is the end of this job for me, because I’m never going to be able to turn that around.” (Source 1).

By his mid-thirties he had landed in a job that worked for him, but the pattern of self-blame persisted: “I didn’t know where else to point the blame and everyone else was saying was my fault. Everyone else was saying that, oh, why are you being so lazy? Why can’t you just, you know, I can’t you just get focused. Why can’t you just do it? Stop being so selfish.” (Source 1).

Lesson for Creators

A pattern you can’t name controls you. Jesse cycled through 30 jobs over a decade because the loop — initial enthusiasm, boredom, forgotten details, decline, exit — was invisible to him. He read it as 30 separate failures. After the diagnosis it was one repeating motif. For creators specifically, the case for naming what you do (and what you can’t sustain) is practical: it’s hard to design around a thing you keep blaming yourself for. Jesse ended up building his entire creative practice — newsletter, book, courses — around the brain shape he spent 20 years trying to outwork.

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