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.