I recently made a dumb (in retrospect) mistake that set me back a lot. Feeling upset and regretful, I spoke to an older family member who reassured me, "yeah, unfortunately there's no way around it; we have to experience these mistakes personally in order to learn from them".
I thought, is that actually true? Can't we learn from other people's mistakes? After all, isn't that the whole point of studying history, or listening to other people's advice, etc? I'm sure that every mistake I could possibly make has been made by countless people before me and discussed in depth somewhere.
This thought inspired me to try to see what I can learn about mistakes by reading about other people's experiences.
I first tried looking at history for examples of famous instances of dumb mistakes made by smart people. I used LLMs and some scripting to (1) generate many examples of mistakes from different periods of history, and (2) summarize/extract/categorize them, so that I could browse by cognitive principle. It generated lots of interesting cases, such as:
Ignaz Semmelweis dismisses need to persuade (Vienna, 1840s)
discovers handwashing saves lives, then refuses to publish evidence
Robert Falcon Scott's pre-committed supply strategy (Antarctic expedition, 1910–12)
layout of supply depots makes retreat impossible
Alfred Dreyfus's lawyers fight the wrong battle (France, 1894–1906)
defense focuses on Dreyfus's innocence rather than the evidence problem
Florence Nightingale's early ignored data visualizations (Crimea, 1854–56)
has the data, but submits written reports nobody acts on
Neville Chamberlain's confidence in his own read of Hitler (Munich, 1938)
mistakes personal rapport for strategic intelligence
However, after reading these historical cases, I felt I wasn't really learning much for some reason. The take-aways just seemed kind of cliche. I turned instead to Reddit, where I might find examples that are more applicable to modern everyday life. I bulk downloaded many threads like "What's the biggest mistake you have ever made?" in r/AskReddit, and similar threads from profession-based subreddits like "What's the biggest mistake you have ever made at work?" and so on.
In the end, however, I still found that reading these stories of other people's mistakes was not that enlightening to me. Whether the anecdote I read was about a doctor, a journalist, or a grocery store clerk, my reaction most of the time was, "yeah, obviously you shouldn't have done that".
My conclusion from doing all this is that these stories mostly give surface-level information and analysis. To make an analogy, realizing you made a big mistake is like discovering a bug in your decision-making process. In programming, when you discover a bug in your code, you can fix it superficially or deeply:
(a) You can patch that one line of code (e.g. add a null check)
(b) You can refactor the whole function to make it cleaner, preventing future bugs
(c) You can re-architect the program to eliminate whole categories of bugs (e.g. use immutable data structures, or don't use threading)
Most of the lessons you read in other people's stories are the equivalent of (a) and (b), e.g. domain-specific advice like "diversify your investments" or truisms like "don't do something risky without a backup plan". However, if you are already a well-read person, you have heard most of this advice before, and I bet even the people writing these stories already had heard this advice prior to making that mistake!
The real interesting stuff is at level (c), and those are the ones that you will rarely find in these types of stories. When a smart person makes a dumb mistake, it is usually due to more subtle things like failed pattern recognition, competing heuristics (e.g. considering one angle but ignoring another), or following a longstanding bad habit that happened not to cause any problems until now. I think advice on how to fix these lower-level issues is more valuable because (1) it is more general, so it applies to more situations, (2) it's less obvious, and (3) it's harder to find than something domain-specific with keywords that can be searched on-demand (e.g. "investing advice", "relationship advice"). My previous post Heuristics for preventing major life mistakes contains some of these principles I learned, but I have many more.
The challenge with getting these kinds of insights is that it's very rare for people telling stories of their mistakes to include the kind of deep introspection that is necessary for you to understand their thought process and where it went wrong. It's like when an LLM does something dumb or gives a wrong answer. Without seeing the LLM's chain of thought (reasoning trace), it's hard to know how to fix it.
I'm wondering, are people here interested in this topic? I think it would be interesting to have some kind of discussion group where someone describes a mistake they made, what their thought process was when they made it, and others can ask questions in a post-mortem format. Everybody could learn from that. Personally, I have made a graph database with about 50 generalizable principles for preventing mistakes, but they are all derived from my personal experience. I could produce something much better if I had knowledge of other people's experiences.
Why it's valuable to study mistakes
In life, good decision-making can benefit you in 2 ways: you can gain new things, and you can prevent losses. Personally, in my youth I already had most of what I need in order to be happy in life: good health, a good family & social environment, and adequate material resources. When I consider the things that I'm unhappy with currently, most of it is due to the simple things I lost through bad decisions, not the things I could have gained but didn't. So that's why I focus on this side.
In society, we hear somewhat conflicting advice about thinking about our mistakes. Sometimes you hear advice like "Don't focus on your past mistakes, look forward to the future". But you will also hear, "learn from your mistakes so you don't repeat them". Which should you follow? I think the former principle may be good advice for the general population or for people who are prone to get sad or angry at themselves. But if you are a rationalist who is used to thinking about all types of topics objectively, your own mistakes can be a goldmine for learning opportunities.
Personally, I'd prefer not to have to make a lot of mistakes in order to gain a lot of wisdom, so I like to make a few extra passes through the postmortem process, and try thinking a bit deeper each time. I often find really valuable and more generalizable ideas on the subsequent passes. Just as you can prove the Pythagorean theorem in many ways (and even using entirely different modes of reasoning), you can identify multiple ways you could have known that a particular decision was not a good one, steeling your defenses against future bad decisions.
I recently made a dumb (in retrospect) mistake that set me back a lot. Feeling upset and regretful, I spoke to an older family member who reassured me, "yeah, unfortunately there's no way around it; we have to experience these mistakes personally in order to learn from them".
I thought, is that actually true? Can't we learn from other people's mistakes? After all, isn't that the whole point of studying history, or listening to other people's advice, etc? I'm sure that every mistake I could possibly make has been made by countless people before me and discussed in depth somewhere.
This thought inspired me to try to see what I can learn about mistakes by reading about other people's experiences.
I first tried looking at history for examples of famous instances of dumb mistakes made by smart people. I used LLMs and some scripting to (1) generate many examples of mistakes from different periods of history, and (2) summarize/extract/categorize them, so that I could browse by cognitive principle. It generated lots of interesting cases, such as:
However, after reading these historical cases, I felt I wasn't really learning much for some reason. The take-aways just seemed kind of cliche. I turned instead to Reddit, where I might find examples that are more applicable to modern everyday life. I bulk downloaded many threads like "What's the biggest mistake you have ever made?" in r/AskReddit, and similar threads from profession-based subreddits like "What's the biggest mistake you have ever made at work?" and so on. In the end, however, I still found that reading these stories of other people's mistakes was not that enlightening to me. Whether the anecdote I read was about a doctor, a journalist, or a grocery store clerk, my reaction most of the time was, "yeah, obviously you shouldn't have done that".
My conclusion from doing all this is that these stories mostly give surface-level information and analysis. To make an analogy, realizing you made a big mistake is like discovering a bug in your decision-making process. In programming, when you discover a bug in your code, you can fix it superficially or deeply:
Most of the lessons you read in other people's stories are the equivalent of (a) and (b), e.g. domain-specific advice like "diversify your investments" or truisms like "don't do something risky without a backup plan". However, if you are already a well-read person, you have heard most of this advice before, and I bet even the people writing these stories already had heard this advice prior to making that mistake!
The real interesting stuff is at level (c), and those are the ones that you will rarely find in these types of stories. When a smart person makes a dumb mistake, it is usually due to more subtle things like failed pattern recognition, competing heuristics (e.g. considering one angle but ignoring another), or following a longstanding bad habit that happened not to cause any problems until now. I think advice on how to fix these lower-level issues is more valuable because (1) it is more general, so it applies to more situations, (2) it's less obvious, and (3) it's harder to find than something domain-specific with keywords that can be searched on-demand (e.g. "investing advice", "relationship advice"). My previous post Heuristics for preventing major life mistakes contains some of these principles I learned, but I have many more.
The challenge with getting these kinds of insights is that it's very rare for people telling stories of their mistakes to include the kind of deep introspection that is necessary for you to understand their thought process and where it went wrong. It's like when an LLM does something dumb or gives a wrong answer. Without seeing the LLM's chain of thought (reasoning trace), it's hard to know how to fix it.
I'm wondering, are people here interested in this topic? I think it would be interesting to have some kind of discussion group where someone describes a mistake they made, what their thought process was when they made it, and others can ask questions in a post-mortem format. Everybody could learn from that. Personally, I have made a graph database with about 50 generalizable principles for preventing mistakes, but they are all derived from my personal experience. I could produce something much better if I had knowledge of other people's experiences.
Why it's valuable to study mistakes
In life, good decision-making can benefit you in 2 ways: you can gain new things, and you can prevent losses. Personally, in my youth I already had most of what I need in order to be happy in life: good health, a good family & social environment, and adequate material resources. When I consider the things that I'm unhappy with currently, most of it is due to the simple things I lost through bad decisions, not the things I could have gained but didn't. So that's why I focus on this side.
In society, we hear somewhat conflicting advice about thinking about our mistakes. Sometimes you hear advice like "Don't focus on your past mistakes, look forward to the future". But you will also hear, "learn from your mistakes so you don't repeat them". Which should you follow? I think the former principle may be good advice for the general population or for people who are prone to get sad or angry at themselves. But if you are a rationalist who is used to thinking about all types of topics objectively, your own mistakes can be a goldmine for learning opportunities.
Personally, I'd prefer not to have to make a lot of mistakes in order to gain a lot of wisdom, so I like to make a few extra passes through the postmortem process, and try thinking a bit deeper each time. I often find really valuable and more generalizable ideas on the subsequent passes. Just as you can prove the Pythagorean theorem in many ways (and even using entirely different modes of reasoning), you can identify multiple ways you could have known that a particular decision was not a good one, steeling your defenses against future bad decisions.