This topic has bothered me for years. So now, in a moment of inspiration instigated by Wait But Why¹ and drinking a glass or two of bourbon, I want to hash it out. It is something I call the Deathbed Fallacy.

“Lord Byron on his Death-bed” by Joseph Denis Odevaere

What is the Deathbed Fallacy?

  1. “I wish I’d had the courage to live a life true to myself, not the life others expected of me.
  2. I wish I didn’t work so hard.
  3. I wish I’d had the courage to express my feelings.
  4. I wish I had stayed in touch with my friends.
  5. I wish that I had let myself be happier.”

All well and good. A bit vague, but seems like solid advice. So what is the problem?

The Fallacy

The deathbed you is not a reliable advisor. Here’s why.

Reason 1: It is not a representative state

The deathbed you is very special in a few ways:

  • They don’t have a future at all. They are about to die, and nothing they think has a bearing on the future. All they have is the present and memories.
  • They think they know their past selves (such as you) very well but probably don’t. More on that soon.
  • Like all your temporal selves, they are locked in a time, place and life situation that does not necessarily correspond to yours.

We should also expect recency bias to play a significant role. We should assume that the people expressing these regrets are in general quite old. Their memories of working a lot should be dominated by the late stages of their careers. The lost friends should be those they miss at old age, not necessarily the people you hung out with in your twenties that you’ve forgotten almost entirely by the time you’re 60.

Reason 2: You don’t know your past selves, but you think you do

But every now and then I find something I wrote or remember a decision I made in high school, which reminds me that my assumptions are all wrong. I was just as smart in high school, I had a lot of information (more than I do now because I’ve forgotten the details). The decisions I made were actually the right ones, and what I think now is wrong, because present me is overly simplistic about past me.

Case in point: for a few years, when I was 14 to 15, a big priority in my life was fitting in, and not be too open about my own ideas and feelings. This goes entirely against both my current ideals and the Deathbed List. So young me would have benefitted from some guidance from present me, right?

Wrong. When I find a diary from that time or talk to a friend from those days about it, it turns out I was probably doing the right thing. My core values were the same as now, only somewhat more 2-dimensional. I valued independence and authenticity back then, too. But what younger me realized, that present me forgot, was that I sucked as a person in a lot of ways and that people, in general, weren’t very fond of me. I also realized that no matter how enlightened or authentic I got, my overall happiness depended quite a lot on how other people saw me, and what relationship we developed.

Today, I probably care too much about what others think. I often blame teenage me for making me so aware of other people’s judgment — why can’t I just focus on cool work and meditation all the time with a select few people I love? But that is just present me shaming past me for dragging himself through an ordeal which benefitted us both. He handled the most pressing matter and passed on the work of undoing the side-effects to me. I just forgot about it and got stuck in regret.

In much the same way, I am now highly career focused. I want to learn a shit lot, I want good jobs, I want money, I want to influence. Deathbed-me would probably scowl and think I’ve gotten my priorities all twisted up. But I am doing this for us. I don’t care about having a career or money, except for as enablers of a good life, a life of freedom, a life in a great city with great people. I believe that hard work can take me places I will enjoy more than where I’d end up if I just focused on being happy in the moment, following the Deathbed List. I’m doing the best I can based on what I know. And that doesn’t come free, I have to make trade-offs. I happen to believe that a lot of the people I would love the hang out with are people in places it is actually hard to get to. The brick walls are there for a reason, and I want to spend as much of my time as possible with the people on the other side of it, so I need to let go of some stuff on this side for a while. Deathbed-me is gonna be pissed, but he’s just a spoiled ingrate. He’s the kid I’m raising, not the other way around.

Reason 3: Most people that die today lived in a world very different to yours

“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

Think about someone you know who lived to be 70 years, 80 years or older. It may be someone alive or no longer with you. They correspond best to the average person in palliative care. Think about the stories they told you about growing up, about working life, about their values. Wouldn’t you agree that it was likely a lot harder for them to live outside the expectations of others? Have we not come a long way when it comes to people being free to shape their own lives? Is it possible, maybe, just maybe, that some people are a bit too good at being “authentic,” to the detriment of themselves and their surroundings, by being a bit self-obsessed and not paying enough attention to duty and the common good?

To someone in their 20s, there is, like, a 50-year delay in the data here. The challenges facing my generation are not the same as that of my grandparents. For example, do you 20-somethings today are better or worse at staying in contact with friends? My grandparents might have had trouble staying in touch, but weren’t stuck on social media. Maybe they were stuck in a cubicle or a rigid moral structure. Maybe they were stuck hiding their sexuality from their friends and families. Maybe they were homeowners by my age, settled down with a family. How similar do you think our lives are?

Who is most guilty of this fallacy?

Conversely, I’ve met quite a few people who are very concerned about living an authentic, carefree life without having a lot of other things figured out first. They don’t have a stable income (or at least the contacts and knowledge required to make some money when they need to), good relationships, and a good grasp of their material priorities. These are struggling artist, miserable drifters or just pretty aimless people with romantic dreams that leave them disappointed with the real world.

In short, people who already have a lot seem to assume that if they never even strived for it, they would be happier. But that striving is often an enabler of the life they now think they want. It is what gave them their family, their network, their passions.

So what’s the alternative?

What I want you to take away is this: Don’t bother with the Deathbed Fallacy. Look at happiness research, which tells you a stable income, focus on relationships and experiences rather than stuff, practicing acceptance, and small things like short commute times make you happier. Get some books on the topic. Reflect on your own past happiness right now, and consider what you should do become more fulfilled both today and for the rest of your time on Earth. Going to work most days and dropping a few friends you don’t have time for may actually be sensible right now if you are in the middle of your career, doing something meaningful. Don’t worry about what some old version of yourself will think of you but focus instead on making sure they are happy and well off, even if they are total ingrates.

Originally published on


  1. What I love about that blog is partly that it always entices me to think about complex concepts, but also that it seems nothing in there is really new to me, but instead it is things I have formulated at some point, but either forgotten or not been able to express so succinctly.

9 days out of 10 I’m a computer scientist, but my background is in “Misc”.