Last weekend, I played a game of chess in which I managed to get two queens on the board. I thought I had the game in the bag at that point, so of course I didn’t notice that my opponent was one move away from checkmate. As soon as his king got space for a breath, he made that move and mated me.

I felt so stupid.

But, honestly, I knew being so far ahead was dangerous for me. I know I tend to get cocky, overextend, and expose myself. I forget to cover the basics like king safety and developing other pieces. I go for flashy moves. I doubt I’m unique.

Biking home, I kept trying to pull out a lesson from the game, but couldn’t really come up with it. Wanting to end the night on a win, I loaded up and played a couple games. The first game I won in the same way I lost earlier: I was on my heels, but my online opponent had left a weak pawn unguarded and I mated him out of nowhere.

He challenged me to another game, and I knew I was in danger of getting cocky. I had just won, so I was feeling good. I knew I could win. I wanted to win. I was good enough to win! I was gonna win!

But then I thought back to earlier in the evening. I needed some mindset that didn’t downplay my ability but also kept me level.

I thought about how I approach martial arts. Grappling with my instructor, I never entertain the idea that he doesn’t know what I’m up to (since he taught me everything), so I always roll with the knowledge that losing is a very real outcome. The result is that I grapple better (I still lose).

I don’t always bring that mindset to peers, but why not?

So, I decided to play chess as if I might lose, as if I was playing a grandmaster.

And I won.


I ended up with a very valuable lesson: play as if losing is actually a possibility.

This doesn’t just apply to chess. For me, it comes up in grappling and sparring, as well as music (don’t underestimate the song). Some other areas:

  • Never underestimate the elements when you’re camping, especially if you’re attempting a challenging feat
  • Play music as if you could mess up (not that you “will” but that you “could”)
  • Write as if that editor is just waiting with a rejection slip
  • Do business as if nobody knows you, which means, be nice. Don’t be “too big for your britches”
  • Teach with the understanding that your students might not have any idea what you’re talking about (my entire year in Korea…and a lot of my math tutoring today)
  • Fly like your engine actually will die, or a gust of wind will blast through just as your about to touch down

You might be thinking that this all sounds like fear-mongering, and I want to make clear that it’s not.

Think of it more as honoring the seriousness of the task at hand by taking it seriously.

It’s like riding a horse: you have to be assertive and confident, but you can’t afford to let your guard down when you’re working with a large, jumpy animal. You have to be attentive, always watching for the horse to spook or make sure it’s not just having a bad day and wants to kick something. If you aren’t attentive, you end up in the hospital. If you are, you just calm the beast down and go for a ride.

It feels so much more comfortable and empowering to say, “You’re sure to win! Nothing can go wrong! Go for it!” But that really is just covering up fear with bravado. My generation has made a culture of it, to the point that we don’t always recognize bravado as a separate state of mind. It’s just part of who we are.

Admitting you’re actually in real ‘danger,’ and are going to keep going anyway, is way more terrifying than psyching yourself up, but it forces you to bring all your resources to bear, which means you will play better.

And if you happen to be in a competitive environment, never underestimate your opponent. Because as soon as you get ahead, the fact that they are losing will sharpen their game and then you’ll be in trouble.