In real life, lottery wins happen, but not often enough to bank on.
Being born a human is huge. Being born in the right country is huge. Being born without genetic problems is huge. Being born to decent parents is huge. These account for the vast majority of a given's person experience pool. Once you get to individual decisions, all the most important things have already been determined. If you're sitting at a place where you feel like you can make all the important decisions yourself, you're already way ahead of the game.
The other problem is that decisions are not fully free and are very strongly influenced by luck, as well. Things like education, information availability, clarity of mind, and, if you want to go there, fluid intelligence, likely influence the quality of your decisions, and that's also luck. Everyone wants to make all the best decisions, otherwise you're saying that lots of people are deliberately trying to reduce the quality of their lives...
It doesn't always smooth out in the long term, except for that in the long run we're all dead.