Turn Maybes into Wins

We all want good things to happen in our lives. Sometimes these good things stem from obvious wins that can be picked up easily, like accepting a new job offer or going on a second date when a first date went well. In thinking about which events in my life were most positively impactful, however, I noticed that many of them were not obvious wins. They were maybes, which I turned into wins.

For example, take buying an island with my friends. This is definitely not an obvious win. It could have lead to fights with my friends, it could have turned into a big money pit, or apathy could have left it undeveloped and relatively useless. However, my friends and I worked hard to turn that maybe into a big win. We’ve had zero fights, have kept costs low, and have built it out to the point of being a great destination for ourselves and our friends and families.

Relationships, particularly marriages, are another one. I got married on the one year anniversary of meeting my wife. People congratulate each other on marriage as if it’s an obvious win, but I’d categorize it as a maybe. I’ve seen people for whom marriage has been a huge negative as well as those for whom it’s been a huge win. The marriage isn’t a win, but what you do with it can be a big win.

Is dropping out of school or quitting your job a win? Like the other examples, it all depends on you.

Sometimes maybes are foisted upon you involuntarily. Is COVID good for you? That all depends on what you do with the changes in your life that have resulted from the lockdowns. Most of my friends and I are in the situation of, “I wish it didn’t happen and wish it would end… but I’m better off because it happened.” It’s a weird paradox.

I was trying to think of a clear loss and couldn’t really think of any other than people dying. I’m sure that there are others, but the point is that almost everything short of a win is a maybe. You have some agency to change things, to influence them, or at the very least use what you’ve learned from them for long term gain.

There’s no point in focusing on obvious wins. You’re going to get them automatically, and you probably don’t deserve much credit for them. The trajectory of your life will be dictated by how you treat maybes.

It’s important to recognize when something is a maybe and not just assume it’s a win. Maybe you’re excited to move to a new city or to get into a new relationship, but that doesn’t mean that it will automatically be good for you. Don’t be complacent but instead treat it like a maybe and then work to ensure that it will be good.

Easy wins are nice, but the biggest gains come from maybes. I suspect that’s because you have more agency to make it not just a win, but the best win for you.

It’s worth being really stubborn about turning maybes into wins, even when they look more like “probably nots”. For example, my previous bank, which I was really happy with, randomly told me that they were going to shut down my accounts (maybe due to a lot of international wires + crypto, but I never found out for sure). At first I was annoyed that I was going to have to go through the hassle of changing my personal finance system, but I quickly realized it was a maybe and not a loss, and I developed the Billionaire Personal Finance system which I’ve been writing about recently.

Don’t rely on easy wins and don’t become too attached to them. Take them if they come. Focus most of your energy on maybes and think about what it would take for each one to become a win, even if it’s a small one.


Photo is me steering a sailboat a few weeks ago in San Diego.

I’m going to Mexico this week!! I’m so excited to have my first international trip in almost 7 months.






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