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Bingo.

I had a bit of a "what am I doing with my life" crisis a few years back when I felt addicted to working, and I made the changes to live a calmer, more enjoyable life at the expense of some income. Will I now regret not leaving more money for my daughter/wife when I go?

We're all stumbling through life to the same conclusion. No one gets to do everything they wanted to.

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I get your point about different sets of regrets, but I really doubt anyone on their deathbed regrets not leaving behind more money. In this case I think you made the right call from a deathbed regrets perspective, trading money for a more enjoyable life.

Really? I guess it likely depends on what age they die at. If you're a 40-year-old guy with a wife and 2 teenagers, and you are dying from cancer, your family is probably going to be left in a much more precarious situation financially if you don't have a large life insurance policy, or a large amount of savings, than if you were a 75-year-old guy who dies with two adult-children, a paid-off house, car, and a wife that receives social security benefits. If you are the 40-year-old, I think you'd be feeling pretty lousy about leaving your family to fend for itself without your financial help going forward. If you're the latter, you know everything is as stable as can be.

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