I knew a guy from a family with a super successful business. Right out of high school he carved off a chunk of his family's business and ran it well enough, so he was always completely set in terms of money and career, but he's always had more artistic sensibilities and curiosities than most business types I've met so I'm not sure he was ever fulfilled by it. After a breakup a few years ago he sold off the rest of the business, started traveling, and never really stopped. I think he's restlessly searching for meaning and community but has zero class consciousness and so he hasn't been able to realize that his position at the top of the pile is what makes that impossible to find. For a while he was trying to pull me out on adventures but I was never able to afford it and wouldn't have been comfortable frolicking around the world with him paying for everything.

I'm not struggling to put food on the table so obviously there's a bit of privilege in saying this, but I wouldn't trade places with him for anything.