I didn't think I'd see a legit response in this thread but there it is.
I actually retired at 36 but went back to work. I had a lot of fun for 2 and a half years but then it was time to get back to work. I know quite a few people who don't need to work, or are just active/passive investors, and I can tell you it's not as good as it sounds. Two problems:
1. Ever heard the expression Idle time is the Devil's play? It's not a joke. I know of a few guys who had way too much money and time on their hands only to create personal disasters which were totally avoidable. I know people are going to laugh at this but the expression "Hookers and blow" is not that far off the mark. More accurately it would be, "Hookers or blow" in my experience.
2. If #1 above doesn't take you down, then just becoming weird is the other risk. You know what, working is good for people. People who don't work often become just weird. They are out of touch with reality. They start to dwell on dumb shit and look for problems.
Some people can pull it off, most can't.