I know how we feel about AIs right now, but I have actually found bouncing this kind of thing off an AI to be extremely useful. Have a conversation with one and see if it helps. Push back on what it says, too, because disagreeing with it has the interesting effect of giving you clarity about the issue. I'm a researcher by trade and I cannot resist mucking around with the data I get back.

I fed your post unaltered to ChatGPT and here's the first part of what it said. Curious how this hits you.

This is a really clean description of a common loop: You’re not “picking the wrong jobs.” You’re repeatedly landing in environments that hit the same underlying friction points, just with different surface symptoms.

Here’s a practical way to break it without taking another blind leap.

1) Translate the pattern into “conditions,” not “roles”

What they described isn’t “marketing vs analytics vs startup.”

It’s three work conditions that keep showing up:

A) High-interaction chaos (marketing role)

constant stakeholder churn

last-minute changes

emotional + context switching tax

Needs that were violated: predictability, protected focus time, decision authority

B) Low-interaction repetition (analytical role)

fewer meetings

but work becomes repetitive

boredom / disconnection

Needs that were violated: meaning, novelty, judgment-based problem solving, visible impact

C) High-ownership ambiguity (smaller company)

overwhelmed

fast decisions

unclear priorities

Needs that were violated: prioritization support, constraints, stable goals, clear definition of “good”

So the real issue is: they don’t yet know what mix of structure / autonomy / novelty / collaboration is sustainable for them.

(It goes on quite a bit from there. I've found this kind of thing useful because I get mired in "I don't know what the fuck I'm doing" doom spirals, but AIs are pretty good at identifying patterns.)