I don't know if money is something to really celebrate. — Clayton Kershaw

I don't know if money is something to really celebrate.

Author: Clayton Kershaw

Insight: Most of us are taught that making more money is the ultimate wins—the promotion, the raise, the deal closed. We celebrate it like we're supposed to. But there's something quietly honest in wondering whether that celebration actually matches what we're feeling. Kershaw, one of baseball's highest earners, isn't saying money is bad or that you shouldn't want financial security. He's pointing at something more subtle: the gap between what our culture tells us to want and what actually feels meaningful once we have it. The real insight is that money is more like oxygen than achievement. You need it to breathe, to take care of people you love, to have choices. But once you have enough, celebrating it the way we celebrate a genuinely meaningful accomplishment feels off. It's useful, but it's not the same as doing something that matters, building something real, or becoming someone you respect. The trap is spending decades optimizing for something that was never supposed to be the destination. This doesn't dismiss financial worry—that's real and legitimate. It just suggests that the moment you can actually afford to think differently about money, maybe that's when you should.