Bravo! Planning your life in order to minimize deathbed regrets has always bothered me, because the nature of humanity is to want what it hasn't got. If you assume that, on average, people make correct decisions to work hard and pursue what matters to them at the opportunity cost of not enjoying quite enough free time, then their final wishes will naturally include the time they gave up to live the life they had. If, however, they had fully indulged the desire to enjoy and maximize free time, their wishes might instead have revolved around the unfulfilled potential thereby relinquished.

The problem, of course, is that the feeling of regret considers what may have been gained without reflecting on what would have been lost.

Now the right way to deal with this is some sort of self-consistent closure, where present you and past you with the same values and access to the same information (which could be anything from zero to complete knowledge of then-future outcomes and downstream effects) would make the same choices including both upside and downside. But that would be too complex for motivational advice, which is primarily about creating an inspirational mood, somewhat about positive first-order consequences, and not even a little bit about recursive self-consistency.

Planning for how you'll feel on your deathbed is like planning for how you'll live in retirement (not speaking of the financial aspects): it's wonderful to know you planned well if you end up in that situation, and there are certainly benefits, but don't forget that you may never get there.

The article is accurate but I think it also misses one other important perspective - getting advice from people who have major regrets of the form "I wish I’d" is sampling for the sort of people who made major mistakes. Just because they are dying doesn't suddenly mean they have their life sorted out. Metaphorically. Arguing with a dying person is a major faux pas but they're ultimately still just people and as fallible as ever.

The people to learn from are the ones who, on their deathbed, say "that life went really well, I did X, Y and Z and it was very rewarding". Which is basically where the article was heading, although going straight to happiness research is probably better again.

I think the author misunderstands the argument. He argues that it is irrelevant what other people believed they should have done when they were close to death.

But the argument should rather be, that you should look ahead of your life right now and consider whether what you will be doing will be something you regret in the future. It is not a fallacy at all, it is introspection about your future. That you might change your views later is essentially irrelevant to the point. The point is to take a completely different perspective on your life, one where your life is behind you.

I totally agree and it really bothers me that people put so much weight into last regrets

I’m in the middle age slump. There is more talk around me about death. Some of our parents died in their 50s and this perspective of ’this might be the last decade’ is creeping in. Yet the same person talking might have still one of their grandparent alive!

I am not so interested in the short life. I am happy today so don’t know how else to prepare for that. I keep worrying about living to a 100. Not very likely, but likely enough to be a risk worth consodering. If I am still to live for 50+ years I can’t start hating everything new that is happening. I probably need to do more learning. Need new friends and cant’t solely live the family life. More sports and active life than before. Retirement is not even on the horizon in this scenario.

I don't know if this is so much a fallacy as it is a questionable assumption which disregards prudential reasoning.

Yeah I get this, always catch myself thinking about how much life is left versus how much I want to actually do. Makes me wonder what even counts as a good use of time.

I think the author fixates too much on this one construction of the idea of deathbed regrets and misses that this idea is just a single modern incarnation of the positively ancient and cross-cultural idea that you should plan your life around the idea that you will die.

Marcus Aurelius wrote: You could leave life right now. Let that determine what you do and say and think. [1]

And the Tao Te Ching: The Master gives himself up to whatever the moment brings. He knows that he is going to die, and he has nothing left to hold on to: no illusions in his mind, no resistances in his body. [2]

A relevant Buddhist concept is called Maranasati [3].

And in the Quran: And donate from what We have provided for you before death comes to one of you, and you cry, “My Lord! If only You delayed me for a short while, I would give in charity and be one of the righteous.” But Allah never delays a soul when its appointed time comes. [4]

And the Bible: The ground of a certain rich man yielded an abundant harvest. He thought to himself, ‘What shall I do? I have no place to store my crops.’ Then he said, ‘... I will store my surplus grain. ... “But God said to him, ‘You fool! This very night your life will be demanded from you. Then who will get what you have prepared for yourself?’ [5]

[0] https://quoteinvestigator.com/2021/03/31/deathbed-wish/

[1] Meditations 2.11 https://vreeman.com/meditations/#book2

[2] 50 https://terebess.hu/english/tao/mitchell.html

[3] https://en.m.wikipedia.org/wiki/Mara%E1%B9%87asati

[4] https://quran.com/en/al-munafiqun/10-11

[5] https://www.biblegateway.com/passage/?search=Luke+12%3A16-21...