Well Kenny I guess the only way to figure it out, is to try it when your ready. Sounds like you've started several very successful companies already, if you don't like retirement start another one. I have friends that love being retired several before 50 and quite a few before 60. I'm past that now and haven't seriously thought about retiring. I have been blessed having two companies I helped create become very successful, the first an auto dealership and the second I'm running now. I tried to semi retire (consulting only) after the auto dealership sold and it didn't work for me. I went into a related business and that has developed into a national company, requiring constant travel, endless meetings and hotel rooms. I wouldn't change a thing, I love the fast pace and constant challenges that arise. Currently changing the company into an employee owned corporation is the thing that drives me now. I think the important thing for anyone, is having a financial plan in place that will fund retirement when they choose to hang them up. Knowing you can retire when your ready, sure takes the pressure off.