the first time i left a large company, i was certain i'd never go back. i had the classic startup convert's zeal. everything big was slow, political, and soul-crushing. everything small was fast, meritocratic, and alive.
then i actually worked at a startup and discovered a different set of problems. the speed was real, but so was the chaos. the meritocracy was real, but so was the burnout. the sense of ownership was intoxicating until i realized i owned the on-call rotation, the customer support queue, and the deployment pipeline all at the same time.
the grass problem
after a year, i went back to a larger company. not the same one. a different flavor of big. and it was better than i remembered, partly because i'd grown, and partly because i now appreciated things i'd taken for granted. well-funded infrastructure. actual mentorship. the luxury of focusing on one problem at a time.
but six months in, the familiar itch returned. the layers of approval. the meetings about meetings. the sense that my work was a tiny gear in a machine too large to feel.
what i actually learned
after a few oscillations, i've stopped thinking about this as a binary choice. the question isn't "startup or big company?" it's "what kind of problems do i want to have right now?"
big companies have resource problems disguised as coordination problems. startups have coordination problems disguised as resource problems. neither is better. they're different shapes of hard.
what actually matters, i've found, is the quality of the people you work with daily and the degree of autonomy you have over your work. those two things predict my happiness better than company size, compensation, or any other variable i've tracked.
the current state
i'm currently at a smaller company again. i'll probably oscillate at least one more time before i find something that sticks. or maybe the oscillation itself is the thing that sticks. maybe some people aren't built for permanent homes, and that's okay.
the only career advice i feel confident giving is this. pay attention to how you feel on Sunday evenings. everything else is noise.