I don't think that most people really know what they want; by "most people" I don't mean you, but just people in general. Instead of looking within to try to figure this out, they pursue illusory goals that never seem to lead to the genuine satisfaction that they hope to achieve. To me, that is sad because they are wasting their brief time on this earth.
The fact that most people (again, not meaning you) never know how much is enough, and would constantly be willing to work for more, seems awful to me if this is a goal that has not come from within. So many work all their lives seeking approval first from their parents, then their peers, or others and never get around to trying to figure out how they themselves want to spend their moment on earth.But then if it doesn't bother them, who am I to say that it is wrong? Perhaps their satisfaction is in the journey. I just wish I felt assured that such people had spent the time to introspect and know themselves before setting off on an endless quest for enough money. Also I am just so glad that I am not in that endless ratrace right now. I so enjoy being the one to determine how I will spend my time each day, and I enjoy knowing that I have enough.
Well written; I found this rather profound. I have no regrets having worked as long as I did (til 60) but could have bailed earlier. DW and I have struggled last 3 years continuing to care for her mother which has severely limited our options. We've made some concrete decisions about placing her in next month or two, which places us in a new era of freedom. So we are finally struggling with how to finally spend our bucks; travel, move, etc. We've been actually spending less than 2% of assets, so OMY clearly not necessary.
Would I go back for a day for $1mm? Sure! It wouldn't interfere with any conceivable plans and if nothing else it'd be fun to give it all to charity (in all honesty I can't say I would though!). In the end I'm sure it would reinforce my assessment that I would not go back to work if you put a gun to my head. Of course, that assumes I'd actually have to be there for more than a day.
This thread, like many, reminds me of a good financial manager friend counseling my father (at ~65) from whom I inherited a strong dose of financial conservatism. He asked my father if he'd figured a way to take his money with him (when he died). I don't think my father thought it funny!