The flip side, is that I'm "told" people on their death bed don't wish they'd earned more money, but they often do wish they'd done that something/whatever big thing that they didn't do.

I certainly haven't met or read about cruisers that have cut out before retirement regretting the decision later. Sure you might miss out on the promotion to CHIEF Bottle Washer, but you had a very rare life experience for which you will have the memories for the rest of your life.

There is also the argument of, you never know when your number may be up. Waiting for the perfect financial moment might mean never going. Going is a risk, but a risk with great potential rewards. The question is, do the rewards justify the risk?