Why my list of times I chose to lose money is one of my most important possessions.

There have been, in my life, a number of times when I have intentionally made decisions that I knew would mean I would make less money or be less influential. I did this because, for whatever reason, it just wasn’t worth it. It wasn’t worth the stress, it felt icky, it relied on me exploiting relationships that I valued. Stuff like that.

And then, years would pass, and someone I didn’t like would come forward talking about all of the money they made doing the thing I didn’t do and I would be angry and jealous.

This is going to happen to you in your life if it hasn’t already. You’re going to make decisions that are not in your best financial interest because they make you happier or more fulfilled or because of your values. You’re going to do that because you’re a good, smart person. But don’t forget that you made that decision, and don’t think you fucked up because you now don’t have as much money as the person who did the thing that you decided not to do.

It is very hard to isolate and store the moment a decision is made. And even harder to call back to it years down the road. I’ve often felt like I somehow am not in control of my destiny even though I very explicitly made a call because, over the years, the realities of the moment in which I made that call have been lost.

So now, whenever I think to myself “If I did this thing, I could make more money, but I’m not going to for reasons,” I send an email to myself with all of my reasons and analysis. Every time, I put the same words in the subject line. For me, those words are “Fuck Money” but you can use whatever you want. So then, in the future, when it becomes clear that I have indeed made a decision that resulted in me not realizing an increase in net worth, I can at least look at the email past me sent saying why exactly he fucked me so hard.

And maybe I’ll think, “OK, past me…you win this time. Maybe you were even right…I may not have as much money as I might have had…I may be watching others prosper from an idea that I had first and likely would have executed better…but I made that call, and I made it for good reasons. And I suppose I’m doing pretty damn good…maybe even better than I would be with that extra cash.”