How do you handle (financial) regret?

Question

A while back I quit a startup because I was unhappy with how management handled a number of situations and I didn't see any signs of that changing for the better.Fast forward a year and the company is thriving, and I realise that I have foregone a massive financial opportunity in terms of compensation.I think the original decision was fundamentally sound then, but it's very difficult to let go of thinking "what if I had stayed".I can't imagine I'm the only among HNers that have been in this situation.How have you managed this internal conflict?

skinkestek · Accepted Answer

Think about this: if you were to blame yourself for that, should you also blame yourself for not investing more in the lottery?Also: Are people who win big in the lottery smart? At the point were you left your best guess was that the chance of winning was extremely slim and the stakes were higher than you wanted. You did a perfectly rational thing. Don't blame yourself.

tom-_- · Answer

1. Startups are a crapshoot, success is very unlikely. Treat it like a bad beat in poker or not buying $gme options at $10/share
2. Did you exercise your options?
3. How far/likely is the startup to exit? You're likely better off financially working those years for an established publicly traded company