Jealousy

I used to become a worse version of myself every time someone else succeeded. I told myself they were lucky. That it wasn't fair. That I deserved it more.

Jealousy works that way. It makes you stop in your tracks while doing nothing to slow the other person down. They stay rich, successful, whatever you define as winning. You just fall behind while standing still.

Naval Ravikant has a useful model for this. You can't be selectively jealous. You can't want someone's money, reputation, or body in isolation — those are outputs of an entire life. To have what they have, you'd have to be them. And once you ask yourself whether you'd swap your whole life for theirs, not just the highlight, but everything underneath it, everything that brought them there, the answer is almost always no.

That model works cleanly in most areas of life. Professional jealousy is harder. In investment and transaction advisory, success compounds. Capital follows the managers with the best track record. One deal begets the next. So when someone in your space closes a fund or lands an anchor investor, it doesn't feel neutral. It feels like a door closing. The jealousy here isn't irrational, which makes it harder to dissolve with a mental exercise. You can't always convince yourself their life is worse than yours, because professionally, right now, it might be better.

What makes it worse is that the picture is distorted. You only see the successes. The failed fundraises, the deals that fell apart — those disappear. Showing failure breaks the compounding effect, so no one does it. You end up comparing your full reality, your doubts, your near-misses, your slow months, against someone else's highlight reel. The jealousy feels rational because the data looks real. But the data is incomplete by design.

What actually works in that context is narrowing the scorecard. Not comparing your position to theirs, but to where you were twelve months ago. Are your deals getting larger? Is your judgment sharper? Is your network compounding? Those are the only numbers that matter, because they're the only ones you can move. Someone else closing a round tells you nothing about whether your next one will close.

I still feel jealousy. I don't think it disappears. But I've learned to catch it faster, and to ask whether I'm playing their game or mine. The answer to that question usually ends it.