I've been at most stages except early-stage startups. The main tradeoffs are - Cash vs lotto tickets - Breadth vs depth of experience - Knowing everyone in

I've been at most stages except early-stage startups. The main tradeoffs are - Cash vs lotto tickets - Breadth vs depth of experience - Knowing everyone in the company vs being more anonymous - Knowing more inner workings of the company vs being shielded from those details - Having broader organizational support vs. doing/learning things for yourself - Some will say work-life balance, but this varies wildly by company and team > I never really learned "the right way" Large companies often do things in very idiosyncratic ways that work for them. These approaches rarely directly translate to startups. Different scale, different tools, and when you're massive, the tools aren't commoditized. The other part of this is your experience. There's a difference between hacking something together that works and intentionally designing something that works. Some of this comes with experience, some with focus and diligence, but it's orthogonal to the size of the company. > I feel like I've also cornered myself with my resume / experience by only working at startups, and might not even be a lucrative candidate for larger organizations. Big companies will happily consider you for mid-level IC roles. They want good engineers. I'd argue it's a little harder to go from a big company to a startup because it's easy to get pigeonholed in a particular role, and you're less likely to be familiar with standard tools everyone else uses. Big companies don't have this problem because no one they're interviewing is familiar with their in-house toolset.