Do you wish you’d have gained tenure at one company longer?

I did stay at Microsoft for a total of 15 years, but in retrospect it's the least interesting place to work. 5% coding, 95% overhead.

Of the places I've worked, none of them had anything where I can now say "I should have stayed there for longer." Amazon and Meta have obnoxious aggressive culture. Microsoft is a place where you can chill out and collect a paycheck and good health insurance. But very boring.

I also worked at some much smaller companies, but not for long. Maybe those are more interesting, but also less stable.