Q: I sold my company five years ago and have built a net worth of ~$10 million, but compared to my friends I feel like a loser and still keep trying hard at startups that stress me out and make me miserable. What should I do?
The monetary number is not the issue–10 million, 10 billion. That’s just a way of counting coups. It’s how you’re comparing yourself to your peers in a way that makes you feel lacking and/or stressed. Which means that you can’t be happy trying to play their game of racking up the big bucks.
If you’ve tied your identity/happiness to what you do/have in comparison to others, rather than tying it to something you actually really do care about, you can never be free of the stress you feel. It sounds as though you’ve already figured that out, but are having a hard time accepting it.
The question is: What would make you feel excited and passionate? What do you really care about? (I’m going to go out on a limb here and say that I don’t think you know what you care about yet.) Are Start Ups the answer?
At the level of the game you are playing, you probably don’t feel you have the luxury of time to step out and sit on the sidelines to catch your breath to think new and different thoughts. But it sounds like that’s exactly what you most need to do. Rarely do good decisions come when someone is stuck in a fight or flight response.
What’s the best way to hold a tiger by the tail and not get eaten? Let go of the tail.