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ciphergoth comments on Things I Wish They'd Taught Me When I Was Younger: Why Money Is Awesome - Less Wrong
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Are you referring to this?:
Depending on how you interpret it, "enough money that you don't have to think about it" could mean a lot of money. And given that this is a famous musician talking...
To expand on Lumifer's point, maybe most people really do care about positional goods. Or rather, they care about the status positional goods bring (and various indirect benefits of status). After all, there does seem to be a lot of independent evidence that most people care a lot about status.
I really don't think it works for them - they keep changing their up their peers until they're not high status any more.
Not high-status within their peer group anymore, you mean. I've heard people talk about this, and for many of them it may not be what they really want, but some people may value being part of a high-status peer group.
(What we really want to know is this: how often do people set out to make money with one purpose in mind, but get sucked into spending more and more money on positional goods they didn't originally want?)