My dad told me after he retired it was his biggest mistake in life.
He'd started a business with a friend in the 1970's that became quite successful in the Detroit Metro area. He retired and like a good Italian, bought a house in Florida and played golf everyday. After a few months he hated his new life, and wished he'd never sold his business. He realized after he retired that his work was something he enjoyed doing, that his clients - most of whom he knew for 20+ years - were people he loved to see and visit. All that changed after he retired and sold the business to my older brother and a another business partner. There was no going back, and that was that.
> bought a house in Florida and played golf everyday
It sounds like this was one of the big mistakes. Hindsight being 20/20 and all, it's hard to see it all now, but it sounds like he could've attempted to transition some of his best business relationships into personal ones, with lunches and/or some other kinds of personal meet-ups. Of course, enjoying the work, it does sound like he sold too soon!
This is still a personal anecdote though. As per the article, we aren't very good at predicting or evaluating what makes us happy. We think retiring and doing "other things" is what we want, but is it? It might be working, running a business, or golfing. You have to figure that out for yourself, and ideally in a way that doesn't require irreversible decisions.
He'd started a business with a friend in the 1970's that became quite successful in the Detroit Metro area. He retired and like a good Italian, bought a house in Florida and played golf everyday. After a few months he hated his new life, and wished he'd never sold his business. He realized after he retired that his work was something he enjoyed doing, that his clients - most of whom he knew for 20+ years - were people he loved to see and visit. All that changed after he retired and sold the business to my older brother and a another business partner. There was no going back, and that was that.