One of my goals in life is to not become impoverished due to bad financial decisions, and think of how many people quit their jobs to try to make a successful game just for their plan to not work out and them then trying to somehow get their lives back in order so they won't become homeless.

Despite this being a question for everyone to answer on their own, continuously failing risky bets and losing everything to it does not look like it will be a popular answer

When I say fucking up I mean things like spending all their savings and maxing out their credit chasing a dream. It could have all worked out for them if things had gone different, but it didn't. As a result they're a lot less happy, don't have housing security and spend a lot more of their life fighting to stay afloat - their life is worse by almost every measurable metric. It's not about failing life, but it is about minimizing your suffering.