I am interested in this topic, but wisdom is hard to communicate for the reasons you mentioned. If wisdom could be summed up, hearing a platitude like "a stitch in time saves nine" will not actually teach you the relevant wisdom, because the phrase does not contain the wisdom. The wisdom is knowing when that idea applies. This is why I learned nothing from your LLM-generated examples: wisdom is contextual, and unless I also learn a lot of information about the context, I haven't learned anything. And doing that takes a lot of time. It is therefore best if the examples are entertaining/well-written, and they don't particularly have to be true, as long as they are representative of real wisdom. And look at that, we've just reinvented literature.
I agree with you up until the point about the examples not needing to be true. That is a big jump; it loses ground truth. Literature is great and you can learn a lot, but in general I think it being optimized for entertainment value (and various other things) is more of a negative than a positive for approaching this topic with rigor. I would say the same thing for movies, TV shows, etc.
I imagine that an efficient way to impact wisdom would be getting a good model of you, and finding a realistic hypothetical situation where your current behavior and beliefs would lead into a disaster, and explaining why.
But that of course is much easier said than done.
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 these are two sides of the same coin. Learning from mistakes is definitely useful, and it's not the reflection itself that paralyses, but the (internalised) social punishment that comes with one's downfalls getting exposed. In a setting where everyone may contribute to making mistakes and discussing them (safely),* nobody gets too attached to a clean record, and the fear of exposure loses its sting. Establishing this requires committed leadership and, as always, trust.
The bottleneck does not lie in the knowledge base. Most institutions I have seen from the inside fail to even leverage their own mistakes -- which would be the most relevant, most precious to learn from! It's a matter of how we talk about mistakes, a question of culture.
One more observation: as stories of bad decisions are told online, LLMs are trained on them and become very adept at giving the kind of Good Advice that would have prevented the mistakes. Will all those witticisms of old people boil down to "should have asked your Claude first" in the future? Mixed with a pinch of "shouldn't have trusted the AI", of course.
*) I'm somewhat proud to say we have a special word for that in German, "Fehlerkultur" ("error/mistake culture"), which isn't to say we don't suck at it.
I'll commit to an online discussion group over discord (voice chat seems best for this) if 2 more people are interested. I have been keeping track of decisions in logs/journals in multiple areas of my life since around 2020, so I think I'd have a lot of material for retrospectives.
I'm interested - what format do you plan on doing?
My biggest mistakes:
Recent (lower stakes) mistakes:
discovers handwashing saves lives, then refuses to publish evidence
From what I remember reading, and a short wikipedia read, something like 'He expected there to be pushback, and so did not want to publish initially, and when he eventually did, he lost his job, got put in an asylum, and beaten to death' would be a better summary. I don't think 'not publishing' was the mistake here. If this is the general quality of the writing on mistakes that you got, then it is not very high.
I would posit that you learn as much from success as you do from mistakes, if you sufficiently analyse them after the fact. We just tend to analyse and post-mortem mistakes more than we do successes. If I think of mistakes I made in hiring or people management, for example, the core learnings were more about people's skills and personalities than anything else. Things I didn't know prior, or should have asked about or tested, for example. Though making the decision and seeing the consequences of it, I learned things.
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.