The subject line is a joke lifted from the movie, We Are The Millers. -- had a kid that got a big tattoo across his chest that read "NO RAGRETS". misspelled of course. It was the funniest line in the movie.
At any rate, I'm a bit stuck in a dilemma that I imagine is common for most peeps targeting a FIRE retirement.
I'm a good 6 to 8 years off from FIRE and trying to decide when to pull the trigger. I could do it at 6 years and live comfortably or do it at 8 years have have luxury. Not Kardashian luxury, but just be able to purchase some of the finer things, as new, versus used. I like a new motorcycle every 4 or so years. I like a new Waverunner every 4 or 5 years. I want a new car every 6 years. These are expensive assets. Retiring at 6 years means buying used. Retiring at 8 years gives me enough cushion to be able to buy them as new. So, it might sound like the answer is simple, just work the extra 2 years. Understand that watersports and motorcycles are my hobby.
The dilemma:
In recent months, I've lost some friends. One was 53, died if heart attack, but had retired early and was enjoying life up to that point. He worked part-time as a youth umpire, fished from a small boat or the shore, and lived a minimal existence. He seemed content.
The other friend was 63, he was still working and was a millionaire several times over. He owned beach houses and luxury homes. Yet, he continued to work even though he had more than enough money. He too had a heart attack and is now dead. He never had a retirement to enjoy what he had. His beach house sits empty as its too big for his widow to manage.
I also lost another friend that was only a month into his retirement. He quit work at 62 and moved to Florida, diagnosed with an aggressive cancer and is now dead. All in a month...
I think both these guys worked too long and should of retired sooner. I know hindsight is 20/20.
I want to know if any post-FIRE peeps have any regrets about leaving the work-force too early. Or, better yet, any advise on how to determine the right time to pull the trigger.