i technically "retired" before 40 and occupied my time by sailing around the carrbbean for a couple seasons.
i'd store the boat on the hard and kited full time during hurricane seasons...
the biggest problem for me was if you were type-a or a workaholic before...you're going to continue to be that same person.
that doesnt really change just because you sell a business and decide to stop working....
i didnt do a very good of sitting around and doing "nothing"... and fighting that need to be "productive" all the times was a much much bigger battle than expected.
once i got thru my reading list, binged watched game of thrones, learned every inch of my boat and how to repair everything..and then perfecting my "game" on colombianas...i got crazy bored.
i ended up starting up another business while still cruising..soon got rid of the boat and did a new start up in a different city...
i tried to set up operations so it wouldnt really matter if i were there or not (with fast internet everywhere and wifi robots nowadays...you can "be there" whenever u need to be...even when half the world away)
in recent years i'd take a 3-4 months off to travel (primarily kite trips) to keep myself from burning myself out again (and also give my staff a break too).
this year...i'll probably be closer to 6 months.
i personally wasnt ready mentally to walk away 100% when i did...
but i think what i'm doing right now is sustainable longer term
i'll problably buy and refit another catamaran pretty soon...but the plan would to simply cruise part time and continue managing remotely from boat. (ie not sell everything and "retire" this time)