Pratchett's lecture at Trinity
For a long time, I've been dubious about "rationality is winning". While it protects against one dangerous line of thought (I was right! It's just that the universe didn't cooperate), it fails to mention a time scale-- sometimes you lose before you win. And sometimes you wander around for a while with no apparent purpose, and then you find something unlikely and valuable.
Pratchett's lecture includes a description of his early life, and I don't think any rational person or any rational parent would have seen his early life as any sort of sensible goal-seeking, or likely to lead to winning in any sense.
Pratchett was a fairly bad student, though he did better when he had less competition. He read all the bound volumes of Punch (the major British satirical magazine), and learned from that classic.
He became a reporter for a local newspaper, a job with modest status and low salary. (In one of his novels, he mentions the voracious appetite of a newspaper-- it's got to have news every day. Somehow, this seemed more intensely true than the large number of other sensible things he said in his books. Looks like I was on to something.)
It seems to me that LW-style rationality would have had him working on being a better student and looking for ways to make more money early on, and he probably wouldn't have written Discworld.
On the other hand, Eliezer is doing quite well, and on yet another and possibly gripping hand, I doubt that going for increasing the probability of success would have started with "think really hard about existential risks".
I feel that part of the problem is that, on average, "try to be a better student and find a well-paying job early on" is good advice. One of the main things I'd like to tell past!me is that I should develop better study habits and go into IT whatever anyone else said. I can't say with absolute certainty it would have made my life better/easier but it probably would have.
For some people (and I won't guess about the proportion of this group relative to the population), "study hard and find a well-paying job" isn't the optimal advice. For Terry Prachett it clearly wasn't and for Eliezer Yudkowsky it wasn't either.
I guess it's really about your competitive advantage, finding your niche and your potential but all of those are hard to discover (and often harder to discover from the inside). I don't think a solution is to stop telling people to study and find a good job, but part of a solution might be to give (young) people more ways of discovering their own potential (preferably at school?). There's a good chance Pratchett's creative writing exercises were noticeably better than those of his peers and from what I read it was clear from an early age that Yudkowsky's advantage didn't lie in strictly academic successes.