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gwern comments on How To Have Things Correctly - Less Wrong
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The difference is necessary vs. sufficient. Money and most purchasable goods aren't a significant source of happiness as best I can tell, and neither is freedom as such. Lower incomes constrain your happiness by increasing your sensitivity to negative externalities and probably also by way of status effects, but removing those constraints doesn't lead reliably to a happy life; granted, I'd expect the miserable millionaire trope to be at least partly sour grapes, but I'm sure there are plenty of independently wealthy people out there that never developed the skills to be happy. Particularly if we're talking old money, since I'd expect people who grew up with that level of privilege to respond poorly to any minor disruption. A billion dollars would give you all the freedom you need to be happy -- but going from that to "a billionaire must be unusually happy", or even "most billionaires are unusually happy", seems to depend on a lot more self-awareness and agency than I think most people of any income actually have.
I also doubt there's much of a discontinuity in the income-to-happiness curve when income reaches what Neal Stephenson called "fuck-you money"; if there was, we'd expect the lottery winner results to look different.
One thing I muse over sometimes in the context of billionaires is that, by and large, we should expect them to be strange and often unhappy people - simply because anyone more normal and well-adjusted would have stopped at, say, $10 million and $10 million typically doesn't accidentally turn into billions. Continuing past the point where all one's real needs are met indicates a bizarrely low estimate of the utility of switching to consumption and away from earning additional money (or perhaps the inability to stop working).
Having worked for / talked to some people who became decamillionaires or higher through startups, a common theme seems to be just being really competitive. They don't care too much about money for money's sake - that's just what we currently use to send the signal "your startup is doing something we really like" in our society.
Or they just enjoy working... I've read quite a few accounts of work being a fairly meaningful part of life, and when you're worth billions, you probably run the company, set your own dress code, can casually fire anyone that annoys you, etc..
I'd also suggest that being a billionaire and enjoying your work probably go hand in hand - it would explain why so many of them work 80+ hours a week...
Agreed that being a billionaire and enjoying work go hand in hand–obviously they enjoyed it enough to put in the work required to earn billions. It's not impossible that someone could say "well, I sort of got dragged into working 80-hour weeks running my company and making billions, but I wish I'd just worked 9-5 for $100,000 a year and spent my leisure time doing x, y, z." But I doubt you hear it often–if they were the kind of person who enjoyed leisure activities more than working, earning, and promotions, they probably would have ended up in the 9-5 job by default–it's hard to accidentally get to be a billionaire.
I think this is unlikely to be the case (that "well-adjusted" people would stop at $10 million), because the processes that lead you to earn $10 million, i.e. being the CEO of a major corporation, aren't things you just quit doing because you felt like "switching to consumption." Also, the type of person who is ambitious and self-driven enough to earn $10 million is likely to be someone who enjoys the process of their work more than consumption anyway.
I don't expect I'll ever earn $10 million, so that is a moot point, but if it happened you could earn millions of dollars working as a nurse, I wouldn't quit nursing just because all my "needs" were met. A lot of my needs (emotional, self-worth, social life) are met at work. Maybe an "inability to stop working" is an adequate description–but how is that unhealthy compared to, say, an inability to stop watching sci-fi movies? If your job provides a significant part of the meaning in your life, it wouldn't make sense to quit it and live a life of luxury. And high earning jobs (like being a CEO), although stressful, are probably much more "meaningful" than sitting in an office all day, at least to the type of people who are likely to succeed in those jobs.
Well, yes, I wouldn't expect billionaires to be normal, but I don't see why that implies unhappiness.