Society would need to be different overall. Everybody is told that things and skills are more valuable than they actually are. If somebody believes this—as most people are inclined naturally—they will naturally fall into the traps you describe. Like you say cynism helps or growing up in a family that has overall more realistic views, or having other key persons (e.g. teachers) that help calibrate this right. Reading LessWrong probably also helps.
I’m skeptical that reading LessWrong helps; I had the Sequences and HPMOR under my belt well before I graduated. I also received the advice that I should take something like a business degree, though maybe not often or forcefully enough to sink in. If someone had taken me to one side, shook me by the shoulders and told me in no uncertain terms the difficulties I’d have, I want to think I’d have chosen differently.
I think cynicism often assumes an unreasonable level of hindsight, though. If we were in another branch of the multiverse where I’m an assistant librarian or working HR somewhere, it would be wrong of me to say that I’d overvalued my degree. And of course I may wind up doing one of those things, in which case it was good for me to have a degree after all, but if I had perfect foresight on graduation day I’d have done something else in the few years between getting the degree and getting the position.
Thinking more about it, I think one of the major factors in these traps is that avoiding them codes them as final actions. There’s a gun on the mantle you never touch, and when you finally pull it down in an act of desperation it winds up being jammed from so many years of disuse. Or there’s money in your mattress you never even look at for a decade, and then when you need it the most half of it’s vanished. In real life last resorts don’t really exist—a problem that no available solution will work on can at least be broken into smaller problems on which further solutions can be attempted.
Thus it was written, “The repeated failures didn’t matter, they only led into the next action in the chain—but he still needed a next action—”
I think the society tells a lot of lies, or at least often lies by omission, and it is difficult to correct these lies, because they exist for a reason—there is some social mechanism that rewards the liars and punishes the truthtellers, for example by raising the status of the liars and lowering the status of the truthtellers.
If anyone asked me about education choice to maximize the chance of getting the job, STEM is the obvious answer. (Although it depends on who asks; some people do not have the necessary skills/traits. I don’t know what would be the right answer for them.) But if I gave such advice in public, I can easily imagine the backlash. Humanities are high-status, STEM is… let’s say medium-status because it is associated with nerds but also with money… definitely lower-status than humanities. The proper way to express it is that STEM makes people merely smart, but humanities make them wise. (Wise = something like smart, but mysterious and higher-status.) Recommending STEM feels like an attempt to give nerds high status, and invites an angry response. Which is the reason why you haven’t heard such advice more often and more strongly (in general, not just on LessWrong).
Problem is that the advice “study humanities, not STEM” is actually correct for a small part of the society; namely for the rich people. If you have so much wealth and connections that you will never need a job to pay your bills, but you still want to study something, because for some weird reason having a university education is considered higher-status than not having one… then humanities are definitely the right choice. You want to know something that other people at least partially understand, so that you can impress them with some smart quotations; you don’t want the inferential distance to be too large. Also, if you study something that makes it quite difficult to get a job, that’s good counter-signaling! As a rich person, you don’t want to be suspected for someone who might need a job. -- The problem is that by saying “study STEM” you now advertise that neither you nor your friends are upper-class. All pretentious people will loudly recommend humanities instead.
I have yet to meet the opinion in the wild that the humanities are better or more worthy of study than STEM, and I’m skeptical that a degree in, say, entomology has anything like the market of a science like physics. (That said, from some cursory checks I’m surprised at the level to which a non-applied math degree seems to affect one’s career, although I’m suspicious that the STEM label lets it get lumped in during analyses with potentially higher earners like statistics, physics and engineering.) And my courses were largely on subjects like web design, running radio stations and using AV equipment, which I wouldn’t put under the same heading as studying history or literature in any case.
More to the point, though, would this line of thinking have saved me my present headache? I knew at the time that STEM was more marketable, of course, but I still underestimated how little my own degree would do for me—I assumed that I would do something in an office setting and be a writer at night. I can’t even chock it up to the degree itself being terrible or just a big counter-signal for the eccentric elite, because plenty of my classmates went on to at least have decent desk-jobs.
Despite all of that, though, if I’d really believed that mathematics or engineering was the only path and that my stalling at precalculus level would simply have to be overcome—that it was this or nothing, in a nutshell—then I think I would’ve chosen a better direction.
Reading this it seems your question was more about the second part of failing: When plan B (or C, or D) fail. Or how to reduce the likelihood that they do—or to have more realistic expectations about that.
I was once running out of options and falling back to plan C and D on a big life topic. It was related to joblessness. A previously existing plan B for such a situation had become unavailable for other reasons (also big ones but that did work out). I scrambled and got a good job offer and started to relax but they postponed the signing for weeks and weeks—while promising it would go thru. It worked out well but there was a point where I resigned and accepted a much lower economic level. Not too bad as Germany has a good safety net.
The level of the safety net depends very much on the country of course but the general pattern seems to be that few people will worry about other people’s economic mishap. Many more ways lead down than up and you are left in the dark which ways lead to the good places.