Investing in Loss

The 2007 Disney movie Meet the Robinsons follows the story of a young boy at an orphanage who's a bit of an engineering wiz and has all these cool invention ideas. But none of them work correctly, so he feels like a failure. Then time travel shenanigans happen, and he ends up in the future where he meets this family, the Robinsons. And he goes through the same process where he tries to impress them by re-making one of his inventions, and it goes haywire just like before. But the family's reaction is very different from anyone he's met before. The Robinsons are clap excitedly, saying "Yay you failed!" and they celebrate and it's a rather funny moment.

This kind of theme appears a lot in motivational posters and images. You see quotes like “Thomas Edison had 50 failed attempts at making the lightbulb before he finally succeeded”, or “Michael Jordan made the most game winning shots in NBA history, but he also missed the most game-winning shots.” The idea is that we need to treat failure as just another stepping-stone on the path to success. We shouldn't shirk away from the possibility of failure, because if we don't embrace that, we'll never achieve success.

So today we're going to talk about re-framing failure, and how we can use that as another motivational tool for ourselves.

Now, words matter when it comes to adopting the right mindset. The statements we make to ourselves can help in shifting this mindset. And I think it's the same thing when we're trying to make this mindset shift from "failure is bad" to "failure is good".

But I think this process starts with the very word itself, failure. It's hard to take this word that we associate with really bad performances and turn it around. No matter what, the negative connotations stay with us.

And this is why I really like the idea of changing the phrase we use here. When something doesn't go right, when we lose a game, or if our code doesn't work the way we would like, or if we can't remember the right way to play the music or the vocabulary word or whatever, we can instead refer to this as "investing in loss".

I got this phrase from Josh Waitzkin, the author of The Art of Learning, who was a world class chess prodigy and then, a bit later in life he became a world champion martial artist. And I really like it because instead of just using this negative word "failure", we're now using a positive word, "investment".

Because what is an investment? An investment is when we pay some kind of price, like taking money out of our bank account, and instead get some asset that will increase in value so that we'll be in a better position later.

And it's the same thing with learning anything. We have to take these experiences that we think of as failures, and understand that while these experiences might hurt our pride and our ego in the short term, we should look for ways to use these experiences to get better long-term value in our skills.

And this topic is very important for me learning chess specifically, because I totally failed at this principle in my younger chess career. This was one of the major things that held me back from getting better.

Part of investing in loss is to actively seek out more difficult and challenging opponents, and I definitely didn't do this as much as I could have because I was afraid of getting my ego bruised. The only way to really gain anything from a loss is to analyze the game and see what went wrong. But I hated analyzing my losses because, again, it hurts your ego to go over this game where you made all these mistakes. I only liked going over my wins because I felt like I was impressing everyone, but there's usually just not as much to gain from looking at your wins.

I also played Starcraft for a bit in college, and there were some even worse patterns. I tended to blame game design and balance issues instead of looking for ways to adapt and improve my own game. But the last thing I would think to do is take a hard look at my own play and admit where I made mistakes.

Until you know what mistakes you're making, you can't possibly correct them. And unless you look closely at the games you lose, or the areas where you aren't as strong, you won't really know what those mistakes are.

As I've said before I want to show the learning process in action. I mentioned in some past articles that I played 25 baseline games of chess to see where I was. And in the spirit of making things public, investing in loss, and generally being OK with losing and trying to learn from that, I'm going to show what is basically a blooper reel, an edit of some of the lowlights from these games. Partially because it's just kind of funny and if I can't laugh at myself I shouldn't be doing this at all. But as we'll see in the next few weeks I learned some important lessons from all these mistakes, and these are helping me to prioritize what I need to be learning.

Before I show the clip I want to make a plug for my Learning Checklist. This is a free download that highlights all these different mentality tricks I've been talking about, like investing in loss, and lots of other great principles to help you on your learning journey. Now without further ado, let's cue the blunder reel. (Skip the first few minutes of this video below).