Why Is It So Hard to Make Money From What We’re Good At?

I’ve been thinking about the disconnect between what we’re naturally good at and whether we can actually make money from it. Some people seem to figure it out, they take a skill or talent and turn it into a career. Others, maybe just as talented, stay stuck, undervalued or underpaid. I’ve been wondering why.

Part of it is structural. The market rewards certain skills more than others. If you’re great at writing code or managing people, there’s a clear career path with salaries attached. But if you’re someone who’s incredible at making people feel seen, or naturally gifted at connecting friends, there’s no obvious job listing for that. You have to carve something out yourself, like becoming a coach, a therapist, or a matchmaker, and even then, there’s a whole separate skillset needed to actually monetize it: branding, pricing, sales, confidence.

That’s the other part: our relationship to our own gifts. Sometimes, when something comes easily to us, we don’t value it. We assume it must not be worth much, because it doesn’t feel like hard work. I’ve caught myself thinking, Why would someone pay me for that? It’s just what I do. But that’s the point, what’s obvious to you is magic to someone else. We just don’t always see it that way.

There’s also fear. Charging money for something that feels personal. Your art / writing / ability to help people may bring up insecurities. What if it’s not good enough? What if I charge and people say no? What if I ruin something I love by trying to make it a business?

I see this in friends too. One friend is a killer cook, like, better than Carbone level. She lights up when she hosts dinner parties, but charging more for her service makes her feel weird. Another friend gives the most thoughtful advice I’ve ever heard, truly life-shifting stuff, but says she could never charge for coaching because “it’s just what she does”.

Meanwhile, there are entire industries built around people with half their depth but twice the confidence.

I don’t have a neat conclusion, but I think this is worth sitting with. There’s a difference between being good at something and believing it has value. And even more of a gap between that belief and actually putting it out there in a way that brings in money. I’m starting to think that closing that gap, for myself and others, might be some of the most meaningful work we can do.