Can you "retire" yet? If you had 15 years at BigCo, that should really be a yes, but with startups it depends a lot more. By "retire" I mean that you can pretty

Can you "retire" yet? If you had 15 years at BigCo, that should really be a yes, but with startups it depends a lot more. By "retire" I mean that you can pretty safely coast by with your annual living expenses set to (depending on your risk appetite) 4% to 10% of your investments. If you can do that, pull the trigger and quit. Commit to only a few years gone, if "indefinitely" is too scary or you don't feel confident in long term market increases. Your professional associates will still be around at various places when and if you decide to work again, making a "resume gap" all the more something not worth worrying much about. After a while, you might explore doing something on your own, or doing consulting, or just teaching yourself some new skills because you suddenly get an intuition about what it is you want to do next. But it should be driven by desire and not a sense of obligation to be generating an income. If after a year you still have no clue or worse still can't really bring yourself to work like you used to, it might be something else that's not quite burnout that's causing you to struggle.