I would often do general consulting while mainly helping with tech, marketing or sales... and I noticed that all of my most important advice no one would follow. It got so extreme that I would often joke that "I know my advice is good because no one ever takes it". David Maister acknowledged a similar thing in his book "Strategy and the Fat Smoker: Doing What's Obvious But Not Easy"
This article strikes a chord of course because its right in line with that thought. Deathbed regrets in that sense are kind of cheap - they knew what they were doing and did it anyway. I think the author is however missing a key feature of this genre though - those regrets are almost always things that are there, that have no deadline and are easily delayed. Spending time with family, working on hobbies or creative pursuits, and so on. What the regretters are failing to attribute is their lack of discipline... and that there is a valuable take away. The genre could really be just a derivative of: "I wish I had been more disciplined in my life"
I think this is an infinitely more useful way of saying what the blogger was attempting to.
There is a flawed prioritization happening that we are seeing have it's natural conclusion on the deathbed - delaying things that feel forever available (spending time with the kids) for things that feel urgent (that critical meeting).
As you said, it takes discipline to avoid this trap. There will always be another urgent meeting, but your children will grow up and go have their own lives.
"Fake urgency" is a terrible poisonous thing that often seeps into the work world. It is the cause of many ills and most deathbed regrets.
He recently passed away a few months ago in August 2025. That's one of the few HN threads I bookmarked because he had a contrarian opinion that I agreed with.
Feels like people on their deathbed are allowed to express their thoughts, trite/trivial or not. When you are literally dying the last thing on your mind should be whether some blogger deems your thoughts valuable or cheap.
May we all get to enjoy those final moments free of the need to perform on stage and express those things we truly wish to pass on to those will hear them.
>When you are literally dying the last thing on your mind should be whether some blogger deems your thoughts valuable or cheap.
to be fair when you're dying the other last thing on your mind should probably be your regrets, so there is some truth in the article.
When people go through dramatic events, not necessarily limited to their literal death, there's often a false sense of clarity. It's not uncommon for people with trauma or loss to suddenly have some conversion of one kind or the other, and it's rarely as good of an idea as they think it is. It seems more sincere because for the individual it's tied to some important event, but I think it's often the opposite.
In software architecture, we often see people rebuild systems from scratch, reproduce the exact same flaws, and end up with the same broken system they sought to replace.
The problem is always that they do not understand the problem. The problem was not the framework, the language, the compute model. It was the problem model.
Having spent a lot of time around that "high driven successful ceo" type, there's a lot of ego involved. There is ego in being needed in meetings. There is ego in working late. There is ego in being the only one who can deliver the thing.
Spoiler, most managers are aware of the ego trap and know how to press that button to get more work from you.
You can't solve the deathbed regret problem by just reading deathbed regrets and swearing to travel or spend time with family. You have to address the root cause of the problematic behavior - ego, dislike of your kids, not actually valuing travel, etc.
“Live next to your relatives because if they get in a car accident and you live across the country you won’t be there to tell them goodbye.”
^Another one I’ve never understood. Like geez, hopefully my daughter doesn’t give up her life dreams just based on the possibility I might be in a freak accident one day...
When my dad was battling cancer a decade ago, the distance from Seattle to Vancouver was maddening. In the end, I regretted not just taking some months off of school to spend time with him in what would be his last year. But now, it's my mom's time around... and I haven't moved back or taken extensive leave. But I'm calling her often enough that we're talking about daily life more more than cancer; enough that we run out of things to talk about. Proximity is nice, but contact is the most important thing.
It’s cathartic to people to hear others cry about what they should have done. Makes them feel better and rationalize their own mistakes.
Not discounting it. There’s comfort in knowing you aren’t alone or the only one to make mistakes, we all do. What’s healthy is realizing it was a mistake, know what you did that caused it, learn from it, and not have it happen again due to a change of behavior. In work, and in life.
Also, life is short, forgiveness is hard, time goes by faster than you think.
The cynic in me thinks that people on their deathbed are about as well considered as people are in general: if you ask most people about some ordinary thing, and life regrets are indeed such a thing, they will give you a canned response that is the zeitgeist regurgitated, and they can't explain why they think what they think, or any related opinions they might have thought instead.
Of course nowadays we have memes to help us completely avoid thinking at all. Ask someone what is best in life, and see how far you get!
Only rarely does one get a considered response. That would be a response that
1) Acknowledges existing thought on the issue. "Socrates mentions regret..." "The mongols thought the open steppe was very important for the good life"
2) Adds personal experience. This can be totally banal, since we don't all live exceptional lives. "I met a girl at the bakery in 1975..." But being banal doesn't mean you can't use the experience to reflect on what regrets actually are, and whether you agree with some POV.
With someone on their deathbed I guess it can be a bit jarring to subject them to the full Oxford tutorial grilling, so I can understand why it can end up being a bit bland.
There is a implicit assumption that many peoples thoughts are insincere before this point and its the only moment where you can really get what people truly value and believe in. I don't think that is true, in many ways you say the thing family/the people around you need to hear. A level of candour has taken over because you don't have to worry about a number of other concerns but at that point you often trying to comfort the people who are going to live with your death.
There is no moment in our lives where we can be trusted to think deeply and express a hard to hear honest thought, and those people that do it often when talking about others are just mean and unlikeable.
What an obnoxious piece. Sorry people’s deathbed regrets don’t entertain you, bro.
Most of us live our lives under the illusion of being in control. As death approaches, many people realize they cannot control their fate and often observe or think of choices they did not make, when they had that agency.
As my mom reached the end, she was very worried about things being taken care of. The house insurance, the taxes, a few other items. Then she talked about things we wouldn’t experience (She was annoyed that she didn’t get to read Robert Caro’s still unpublished last book together), and then a few regrets about things that were done or not done.
This translation of Aeschylus always captures this subject for me:
“He who learns must suffer, and even in our sleep pain that cannot forget falls drop by drop upon the heart, and in our own despair, against our will, comes wisdom to us by the awful grace of God”
Wisdom comes from suffering sometimes, and sometimes the most important wisdom you learn seems simple and trite, or is it?
Deathbed regrets aren't fun at all. Deathbed wishes for their next life are much more interesting!
For example, Gil Amelio—former CEO of Apple—once expressed that he wanted to be reborn as a woman owning/working a vineyard in Southern France. That was so specific and interesting, I still remember it.
Wishing you used social media less doesn't exactly spark the imagination.
Odd how some pieces of info come in one's life synced with one's needs. I'm in adjacent rooms with my mom and sister and we're all on phones. Just had the thought about regretting this in a potential future and then decided to continue my phone-strolls on HN. Found this advice/regret and it maxxed on instantaneous salience.
>don't value regrets packaged as advice, especially from people who never acted on their advice
>Better advice comes from things people actually did.
What happens when it takes quite a bit more focused effort to do something like not be on "social" media than it does to idle along with the mainstream?
The line is pretty blurry to begin with, and can be a moving target making it hard to know for sure whether you are doing, not doing, or being done :)
I have a love/hate relationship with deathbed advice.
I still go around quoting: No one at their deathbed says "Man, I wish I had spent more time at the office!"
On the flip side, I've noticed the older one is, the longer their list is of "things that don't matter." (e.g. Don't focus so much on wealth, career, etc). It was years before I realized that I've encountered very old people who say "None of it matters", and that perhaps they are not giving sage advice, but are merely changing preferences as they age.
@dang something about this website triggering content blocking filters. hate to say that i don't have time to investigate but it seems worth mentioning
This article is akin to something I wrote a while ago - https://jonpauluritis.com/articles/on-giving-better-advice/
I would often do general consulting while mainly helping with tech, marketing or sales... and I noticed that all of my most important advice no one would follow. It got so extreme that I would often joke that "I know my advice is good because no one ever takes it". David Maister acknowledged a similar thing in his book "Strategy and the Fat Smoker: Doing What's Obvious But Not Easy"
This article strikes a chord of course because its right in line with that thought. Deathbed regrets in that sense are kind of cheap - they knew what they were doing and did it anyway. I think the author is however missing a key feature of this genre though - those regrets are almost always things that are there, that have no deadline and are easily delayed. Spending time with family, working on hobbies or creative pursuits, and so on. What the regretters are failing to attribute is their lack of discipline... and that there is a valuable take away. The genre could really be just a derivative of: "I wish I had been more disciplined in my life"
I think this is an infinitely more useful way of saying what the blogger was attempting to.
There is a flawed prioritization happening that we are seeing have it's natural conclusion on the deathbed - delaying things that feel forever available (spending time with the kids) for things that feel urgent (that critical meeting).
As you said, it takes discipline to avoid this trap. There will always be another urgent meeting, but your children will grow up and go have their own lives.
"Fake urgency" is a terrible poisonous thing that often seeps into the work world. It is the cause of many ills and most deathbed regrets.
Fyi... this blog article also mentions another article, "The Deathbed Fallacy".
HN discussed that a few months ago and the most upvoted commenter happened to have a terminal illness and disagreed with some of it. https://news.ycombinator.com/item?id=43944467
He recently passed away a few months ago in August 2025. That's one of the few HN threads I bookmarked because he had a contrarian opinion that I agreed with.
Feels like people on their deathbed are allowed to express their thoughts, trite/trivial or not. When you are literally dying the last thing on your mind should be whether some blogger deems your thoughts valuable or cheap.
May we all get to enjoy those final moments free of the need to perform on stage and express those things we truly wish to pass on to those will hear them.
>When you are literally dying the last thing on your mind should be whether some blogger deems your thoughts valuable or cheap.
to be fair when you're dying the other last thing on your mind should probably be your regrets, so there is some truth in the article.
When people go through dramatic events, not necessarily limited to their literal death, there's often a false sense of clarity. It's not uncommon for people with trauma or loss to suddenly have some conversion of one kind or the other, and it's rarely as good of an idea as they think it is. It seems more sincere because for the individual it's tied to some important event, but I think it's often the opposite.
This is a tough one.
An advanced cancer diagnosis changes the mind and brings a level of clarity that I had never before experienced, about what is important.
Being forced to face one's mortality is not pleasant but it can be enlightening. And then truly enjoy the experience of being.
I think the question is, if everyone has similar "deathbed" advice, then what can you learn from that?
In software architecture, we often see people rebuild systems from scratch, reproduce the exact same flaws, and end up with the same broken system they sought to replace.
The problem is always that they do not understand the problem. The problem was not the framework, the language, the compute model. It was the problem model.
Having spent a lot of time around that "high driven successful ceo" type, there's a lot of ego involved. There is ego in being needed in meetings. There is ego in working late. There is ego in being the only one who can deliver the thing.
Spoiler, most managers are aware of the ego trap and know how to press that button to get more work from you.
You can't solve the deathbed regret problem by just reading deathbed regrets and swearing to travel or spend time with family. You have to address the root cause of the problematic behavior - ego, dislike of your kids, not actually valuing travel, etc.
Then the ongoing work of prioritizing can happen.
“Live next to your relatives because if they get in a car accident and you live across the country you won’t be there to tell them goodbye.”
^Another one I’ve never understood. Like geez, hopefully my daughter doesn’t give up her life dreams just based on the possibility I might be in a freak accident one day...
When my dad was battling cancer a decade ago, the distance from Seattle to Vancouver was maddening. In the end, I regretted not just taking some months off of school to spend time with him in what would be his last year. But now, it's my mom's time around... and I haven't moved back or taken extensive leave. But I'm calling her often enough that we're talking about daily life more more than cancer; enough that we run out of things to talk about. Proximity is nice, but contact is the most important thing.
It’s cathartic to people to hear others cry about what they should have done. Makes them feel better and rationalize their own mistakes.
Not discounting it. There’s comfort in knowing you aren’t alone or the only one to make mistakes, we all do. What’s healthy is realizing it was a mistake, know what you did that caused it, learn from it, and not have it happen again due to a change of behavior. In work, and in life.
Also, life is short, forgiveness is hard, time goes by faster than you think.
The cynic in me thinks that people on their deathbed are about as well considered as people are in general: if you ask most people about some ordinary thing, and life regrets are indeed such a thing, they will give you a canned response that is the zeitgeist regurgitated, and they can't explain why they think what they think, or any related opinions they might have thought instead.
Of course nowadays we have memes to help us completely avoid thinking at all. Ask someone what is best in life, and see how far you get!
Only rarely does one get a considered response. That would be a response that
1) Acknowledges existing thought on the issue. "Socrates mentions regret..." "The mongols thought the open steppe was very important for the good life"
2) Adds personal experience. This can be totally banal, since we don't all live exceptional lives. "I met a girl at the bakery in 1975..." But being banal doesn't mean you can't use the experience to reflect on what regrets actually are, and whether you agree with some POV.
With someone on their deathbed I guess it can be a bit jarring to subject them to the full Oxford tutorial grilling, so I can understand why it can end up being a bit bland.
There is a implicit assumption that many peoples thoughts are insincere before this point and its the only moment where you can really get what people truly value and believe in. I don't think that is true, in many ways you say the thing family/the people around you need to hear. A level of candour has taken over because you don't have to worry about a number of other concerns but at that point you often trying to comfort the people who are going to live with your death.
There is no moment in our lives where we can be trusted to think deeply and express a hard to hear honest thought, and those people that do it often when talking about others are just mean and unlikeable.
What an obnoxious piece. Sorry people’s deathbed regrets don’t entertain you, bro.
Most of us live our lives under the illusion of being in control. As death approaches, many people realize they cannot control their fate and often observe or think of choices they did not make, when they had that agency.
As my mom reached the end, she was very worried about things being taken care of. The house insurance, the taxes, a few other items. Then she talked about things we wouldn’t experience (She was annoyed that she didn’t get to read Robert Caro’s still unpublished last book together), and then a few regrets about things that were done or not done.
This translation of Aeschylus always captures this subject for me:
“He who learns must suffer, and even in our sleep pain that cannot forget falls drop by drop upon the heart, and in our own despair, against our will, comes wisdom to us by the awful grace of God”
Wisdom comes from suffering sometimes, and sometimes the most important wisdom you learn seems simple and trite, or is it?
Deathbed regrets aren't fun at all. Deathbed wishes for their next life are much more interesting!
For example, Gil Amelio—former CEO of Apple—once expressed that he wanted to be reborn as a woman owning/working a vineyard in Southern France. That was so specific and interesting, I still remember it.
Wishing you used social media less doesn't exactly spark the imagination.
BTW: Yes, I know he's still alive :)
Odd how some pieces of info come in one's life synced with one's needs. I'm in adjacent rooms with my mom and sister and we're all on phones. Just had the thought about regretting this in a potential future and then decided to continue my phone-strolls on HN. Found this advice/regret and it maxxed on instantaneous salience.
>don't value regrets packaged as advice, especially from people who never acted on their advice
>Better advice comes from things people actually did.
What happens when it takes quite a bit more focused effort to do something like not be on "social" media than it does to idle along with the mainstream?
The line is pretty blurry to begin with, and can be a moving target making it hard to know for sure whether you are doing, not doing, or being done :)
I have a love/hate relationship with deathbed advice.
I still go around quoting: No one at their deathbed says "Man, I wish I had spent more time at the office!"
On the flip side, I've noticed the older one is, the longer their list is of "things that don't matter." (e.g. Don't focus so much on wealth, career, etc). It was years before I realized that I've encountered very old people who say "None of it matters", and that perhaps they are not giving sage advice, but are merely changing preferences as they age.
@dang something about this website triggering content blocking filters. hate to say that i don't have time to investigate but it seems worth mentioning
(do people still at dang? don't read here often anymore)
I have 4 different plugins running right now filtering out bad sites, and I'm also reducing trash websites via DNS.
You're going to need to be far more specific.