People who have earned enough wealth to not for a living do, though those who've worked hard enough to do that typically don't have much in their life but work.
People who simply have enough wealth to not have to work are on a hedonistic treadmill most of the time
You think so? Have you been in that position? I was. It's not what you think it is. Also unless you want to spend your wealth pretty fast (money has a half-life time like radioactive elements, doesn't depend on quantity) you have to work to keep your wealth, and it's not less nerve-racking than spending your 8 hours at work and forgetting it until next morning.
No, I haven't been, just know some people who are.
I don't understand what you're referring to. Where was your money going? I understand you still have expenses when you aren't working, but the expenses don't scale up on their own.