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gwern comments on Optimal Employment - Less Wrong
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Upvoted. This is really interesting.
I'd very likely not do this myself, though. I've noticed there are two kinds of attitudes toward jobs (and I've seen rationalists of both stripes). Some people really want their career to be an extension of their interests and identity and perhaps their prestige: "I'm a scientist," "I'm an artist," "I'm a programmer," "I'm a doctor," "I'm a teacher," etc. They wouldn't want to make the same money in less time by a different route, they want to work in that particular field.
Some people, on the other hand, basically see their job as a source of income, which they can use to pursue their interests elsewhere. They're optimizing for money and free time, which means they look at a much wider range of money-making possibilities. (The most extreme example would be The 4-Hour Workweek, in which the money comes from a passive income stream, not a "career" at all.)
Your advice is geared more to people in the second category. I'm in the first. That doesn't mean it's not good advice -- if you want money and free time to pursue an interest, then hospitality jobs in the outback sound like a great idea, given your evidence.
I'm curious, though -- does anyone think that one attitude is better than the other? Or is it just a matter of individual preference? Job-as-income-stream, or career-as-personal-identity?
I think there's an argument to be made that the first attitude (personal identity) is instrumentally superior (even as it may well be epistemically inferior). Someone whose identity is wrapped up in their job may work far harder at their job and so eventually gain greater skills or produce better work in their chosen profession than the person who strives for the same results but as a hobby and works in another field. It's hard to have two masters.
For example, think about rock stars or pro sports. Objectively, epistemically, these are absolutely lousy careers. Tiny chance of success and even the mega-hits don't do so well. Not to mention all the issues like dying prematurely, which seem to be intrinsic to the careers. (See the recent New Yorker about NFL cutting a few decades off its players' lifespans, or look at probably the wealthiest musician ever - Michael Jackson.) But if you believed this, you're never going to become a rock star.
A would-be rationalist rock star is like the two-boxing decision theorist faced with Newcomb's Problem. 'Oh, if only I could brainwash myself to take one box! Then I would be much wealthier.'
Or so the argument would go.