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Crippled CEO Blog #062: Lessons from Chess

Crippled CEO Blog #062:

If you’ve been reading these for a while, then first, thank you, that’s very cool of you, but also, you know that I’ve been making a fairly serious attempt to get as good as I can at chess. I started taking lessons three times a week from International Master (and all around great guy) Vitaly Neimer in July, and I spend a good chunk of my free time playing chess, watching videos about chess, and reading about chess. (And yes, I’ve seen the show. It’s great.)

There are three insights chess has put a spotlight on for me, which apply to real life, that I wanted to share with you — and I don’t mean the typical “thinking three steps ahead” trope you might expect. 

  1. Chess Blindness 

When you first start playing chess, it is very common to just give away an important piece, like a queen, for no reason. You are looking at everything so intensely, but somehow you just missed this very obvious thing right in front of you. While this does get better as you practice, it doesn’t seem to ever go away completely, and there are tons of examples of even world class level grandmasters somehow going “blind” for a moment and donating a piece or making an obvious mistake. 

As you experience this over and over again (and I definitely have), you realize how much more susceptible you are to missing something important right in front of you because you’re focused elsewhere, on something far less important, than you think you are. You THINK you will notice this huge, critically important issue, but if you’re distracted elsewhere, there’s a good chance you might not. In chess, we are taught to take a moment each turn and look for checks, captures, and threats, a sort of mental safety check list, to try to help mitigate this. In real life, you can do something similar, but just being aware how likely you are to miss something both major and obvious will help you to be more careful. 

  1. Time pressure 

All “real” chess is played with some kind of time control. Each player is given a set amount of time to play all of their moves. This can be two hours or two minutes or anything in between. Either way, when it’s your move, your clock is ticking down. 

“Time pressure” is the DRAMATIC impact on your play that occurs when you are low on time. Even the best players in the world become mere shadows of themselves when the clock is getting close to zero. 

We all know that we are prone to mistakes when we are rushed, or that we don’t think as clearly, but it’s hard to appreciate the full extent of how compromised you are until you see it play out on that 64 square board. In chess, you can go back and look at your game again, so the idiotic mistakes that you made because of the time pressure are clear as day, right in front of you. You typically can’t do that in real life, so it’s hard to speculate on what you would have done differently, but chess makes it brutally apparent. Being pressured by a lack of time makes you dumb. You do things that you would never in a million years do otherwise. Tim Ferriss refuses to jump on any opportunity or investment, no matter how good it seems, if there is a short deadline, or if he feels pressured by time. And it makes sense. 

Outside of chess, deadlines and time pressures are almost always artificial. You can almost always get more time if you need it. The sneaky thing about time pressure is that, in the moment, you know that you are rushed, but you still think you’re making the right decision. It is only after the fact, when you have more time to think, that you realize your mistake. The solution to this is, whenever possible, like Tim, don’t make decisions when you’re short on time. Prioritize giving yourself more time to think. Ask yourself, “What is the absolute worst thing that will happen if I don’t make this decision right now?” Usually, it’s not that bad. Give yourself the time, even when you think you don’t need it. You do.

  1. Tilt

I first learned the concept of “tilt” playing poker. It has the exact same meaning in chess. The name comes from pinball machines, which would display the word “tilt” as an error message when the table was lifted or moved violently, as often happens when someone is upset. In chess and poker, someone is “tilted” or “on tilt” when something goes wrong, they get upset, and then start making bad decisions and playing poorly. 

My first ever blog post, #001, was actually about this. Scientific studies have shown that we lose a substantial number of IQ points when we are in a bad mood, and the more upset we are, the worse it gets. You can read that whole post right here:

The basic idea of the post, and the lesson we can learn from chess, is that you’re incapable of making the best decisions when you’re upset by something terrible that has happened to you. You are tempted to try and fix the problem right away, but doing so only makes it worse. The solution is to wait. Don’t do anything until your state of mind improves. Waiting on purpose isn’t laziness, it’s a choice, and an action. And it is often the best one.

There are a ton of other lessons we can extract from chess and apply to our lives. The idea of prophylaxis (seeing a problem coming, and protecting against it ahead of time), how improvements come slowly, in inches — not miles, and so on. But I thought these three were the ones you don’t hear about the most, and were the most interesting to me. Now you can benefit from them without spending a couple hours a day getting beat up by better chess players.

PS: I’m giving a few of my friends chess lessons with IM Vitaly as Christmas gifts. I think it’s a pretty rad gift. If you would like to, as well, let me know, and I will put you in touch with him, or just go to his website 

(I bet you can imagine someone who would like this. You should send it to them. You should also subscribe to my weekly text message so you get notified as soon as I post the latest blog. All you have to do is send a text to the phone number 484848 with the word CRIP and the magic will happen.)

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