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Comment by nostrademons

I've switched between startups and Big Tech multiple times. I worked for startups before and after college, left to found my own, ended up at a FAANG, quit to found more startups, and then went back to my previous employer. I was effectively financially independent (went back with more savings than I started with, after 6 year with no income), but I burned myself out. It's been almost 3 years since the last startup, during which I've written very little code (I've been an architect and then a manager), and I'm only just starting to enjoy coding again.

To me, the biggest red flag in your post is "I'm starting to feel not so happy with my current route". I had started to feel like my startup ideas had run their course around 3 years in, but I doubled down on a complicated one because I can be hella persistent and kept it going for another 3 years. Big mistake. When your feelings start telling you it's time to throw in the towel, it's time to throw in the towel. I don't regret leaving the security of a big company to play the startup game, but I do regret sticking with it for so long, even when evidence had mounted that the market had turned and there wasn't really an opportunity there.

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