My biggest problem is that I dislike my job but it has potential to pay off big and allow me to retire (Or at least, semi-retire) in ~5 years off the stock options. Retiring at 45 seems pretty appealing. I could finally catch up on my massive library of games I've been wanting to play, not to mention reducing my alarm clock usage to likely 10 times a year, rather than 5 days a week.
it has potential to pay off big I hope you’re not talking about a startup lottery
And I do recognize that it's just that - a lottery. We could fail and I end up unemployed with nothing. Or a funding round could dilute my stock options to worthlessness.