It's graduation time, so that means it's time to hear about what people do and do not regret on their death beds. Intended lesson: Pursue your dreams! Don't worry about money!
I can find no systematic research about what people on their deathbeds do in fact say that they regret. A PsycInfo database search of "death*" and "regret*" turns up this article as the closest thing. Evidently, what elderly East Germans most regret is having been victimized by war. There's also this inspiring pablum, widely discussed in the popular press.
Let's grant, however, that the commencement truisms have a prima facie plausibility. With their dying breaths, grandparents around the world say, "If only I had pursued my dreams and worried less about money!" Does their dying perspective give them wisdom? Does it matter that it's dying grandparents who are saying this rather than, say, 45-year-old parents or high school counselors or assistant managers at regional banks? The deathbed has rhetorical cache. Does it deserve it?
I'm reminded of the wisdom expressed by Zaphod Beeblebrox IV in Hitchhiker's Guide to the Galaxy. Summoned in a seance, he says that being dead "gives one such a wonderfully uncluttered perspective. Oh-ummm, we have a saying up here: 'life is wasted on the living'."
There's something to that, no doubt. Life is wasted on the living. But here's my worry: The dead and dying are suspiciously safe from the need of having to live by their own advice. If I'm 45 and I say, "Pursue your dreams! Don't worry about money!" I can be held to account for hypocrisy if I don't live that way myself. But am I really going to live that way? Potential victimization by my own advice might help me more vividly appreciate the risks and stress of chucking the day job. Deathbed grandpa might be forgetting those risks and stress in a grandiose, self-flagellating fantasy about the gap between what he was and what he might have been.
A smaller version of this same pattern occurs day by day and week by week: Looking back, I can always fantasize having been more energetic, more productive, having seized each day with more gusto. Great! That would have been better. But seizing every day with inexhaustible gusto is superhuman. I forget, maybe, how superhuman that would be.
Another source of deathbed distortion might be this: To the extent one's achievements are epistemic and risk-avoidant, their costs might be foolishly easy to regret. Due to hindsight bias, opportunities sacrificed and energy spent to prove something (for example, to prove to yourself that you could be successful in business or academia) or to avoid a risk that never materialized (such as the risk of having to depend on substantial financial savings in order not to lose one's home) can seem not to have been worth it: Of course you would have succeeded in business, of course you would have been fine without that extra money in the bank. On your deathbed, you might think you should have known these things all along -- but you shouldn't have. The future is harder to predict than the past.
I prefer the wisdom of 45-year-olds -- the ones in the middle of life, who gaze equally in both directions. Some 45-year-olds also think you should pursue your dreams (within reason) and not worry (too much) about money.