Yes, I feel like this over-ambition and risk has put me in a similar position. I still own around 300k worth of stock which is not liquid in one of the start-ups but it has been 8 years now. On the other hand I realize that with my background I would never be able to even get a job at FAANG in a first place so I really cherish the experience I got in one of the startups like opening the offices in different countries, travelling and getting clients (I am in tech sales). However looking back, I partially regret the decision to always strive for the outsized return as an employee you get 1 bet for 4 years of vesting, instead of many bets that VCs have. I recently landed a job in a more boring place and increased my income by around 120%, living the boring tortoise life with more politics, but I realised I stopped worrying about the future and really enjoy spending my free time on staying sane. In the end though, I always say that if I would have stayed in my own country and lived the super boring life, I would regret it in the end and so far it has been an exciting ride.