I "retired" for a month, first two weeks I was so bored just exercising and consuming content, then got kind of depressed, and wound up making plans to start a new business. Then I took a new role at a startup and went back to the grind. I came to the conclusion I just can't stop working. If it isn't for a company then I'd probably start a non-profit and build a new thing that is more idealistic. My dad was the same…
Is that all you wanted to do? I'm pretty sure if I could afford to be retired it would be a long, long time before I got bored. Yes I would exercise more and catch up on TV and movies that I've missed over the years, but I also have a lot of hobbies that I would like to work on. There are local organizations I would like to volunteer for. There are lots of classes I would want to take or audit. I'd visit friends and family I haven't seen in years.
I might even be like your dad and find a job that I enjoy doing. That's a whole different thing than working because you have to.