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Winning Isn’t As Fun As It Seems

Daily Stoic Emails

There’s an old joke: When the Gods wish to punish us, they give us everything we’ve ever wanted. Look at most people who win the lottery. Look at most famous people. Look at most world leaders. To borrow an expression from one particularly unhappy world leader, what do they look like? They look like they’re tired of winning. Because winning isn’t actually as fun as it seemed like it would be…and most of what we want to win turns out to not really be worth it.

This was Marcus Aurelius’ point. When we look at history and other people, it’s hard not to see “how trivial the things we want so passionately are.” But what if you don’t realize that yourself? Or rather, what if you don’t realize that the presidency or a billion dollars isn’t that meaningful until after you’ve given up everything for it? After you’ve traded your marriage or your principles or your youth to get it?

“Now you’re free of illusions,” says a character in Ralph Ellison’s Invisible Man. “How does it feel to be free of one’s illusions?” The protagonist can only answer, “Painful and empty.” In this way, we are almost lucky not to get everything we want, to not be allowed our trivial passionate yearnings. Because we are allowed to continue in ignorance. We don’t have to do the hard work on ourselves, and really look in the mirror.

Of course, this is what a philosopher does all the time. Instead of hiding behind luck’s protection, or instead of continuing to lie to themselves that more, more, more will make them happy, they actually probe themselves. They question their desires. They look into the future and ask, “What would happen if all my dreams did come true? Why would I suddenly be happy then? Why can’t I be happy now instead?”