Has anyone retired early and come to regret it later?
I've yet to meet anyone who regretted an early retirement.
I retired in 2020 at 59 and have loved it.
I mentioned this upthread, but I'll touch on it again. Everyone treats the question of early retirement as a financial problem to be addressed with spreadsheets and financial analysis and investment forecasts and debt payoff schedules. That's part of it, sure, but what's the real question to be answered? Regret-free retirement is
not a pure math problem!
I submit that the real question is, "What do I need to have a
happy retirement?"
Addressing that should lead to some introspection about the things that actually bring joy and happiness to your life, and once you understand what those things really are, you may find that you can achieve them for less cost than you think. Failing to address it can lead to a retirement that's less than satisfying.
For me, coming to an understanding of my personal happiness generators was key to a happy retirement, and to a happy life in general for that matter.
Simple example: SWMBO and I enjoy dining out with friends from time to time. What makes us happy is the time with friends in a pleasant environment, and we can derive just as much pleasure from that with a meal at Golden Corral as we can at Ruth's Chris. It's the conversation, the laughter, the camaraderie that matters, much more than the quality of the steak (and I love a good steak as much as anybody).
Another example: I absolutely love taking a fast performance vehicle along a fun, winding road. That does not require a Ferrari! I have a Triumph Daytona 675 that I bought new for $13k and it will walk away from a Ferrari, and for me is more fun anyway.
I enjoy flying. Would I be having more fun in a new Cirrus than I am in my 1969 Musketeer? Maybe a little, but not 20x as much.
There's usually a way to make the spreadsheet work out, as far as paying the bills and healthcare and groceries are concerned. The real trick to not regretting early retirement is to understand what
you personally will find satisfying and then figuring out how to make that happen within the figures the spreadsheet is giving you.