How Chess is Like Business

When I was a kid, and my grandpa was teaching me how to play chess, I hated it. Sitting for an hour, trying to think was incredibly boring. Now I love it. Sitting for an hour, trying to think is actually fun. I’ve played chess in different ways:

• Like normal people
• Drunk with my friends (great drinking game)
• Over email with my grandpa, since we now live on different continents. It’s interesting because you have a day to think over your move. Sometimes our moves took a week. It’s also interesting because my grandpa knows how to use email since 1996.
• A while back I downloaded a chess app onto my phone, and can play a blitz game while passing time. This is especially insightful, because I can play A LOT of games and can take back moves, which lets me learn from mistakes much faster. For example, at the end of the game, I can track back to that ONE critical move that started started the path towards winning or losing. This has taught me a lot about chess, and the several parallels it has with business:

1. One wrong move can ruin the game. Its obvious when taking back moves in a lost match to see what caused the chain of events. When playing a strong opponent (Android or my grandpa), one mistake and you’re done. I had several situations in life, where I worked very hard towards something, made 1 mistake, and lost in that particular situation.

2. There’s usually a rematch. Really, it’s no big deal. There’s always another opportunity ahead. I just have to not make the same mistake again. And if I do, that’s probably ok too. There’s usually another rematch… But that’s it, after that you’re f’ed.

3. You have to think at least 2 moves ahead. Your opponent is.

4. The end game is especially critical. Stakes are higher with few pieces on the board. Mark Suster has a fantastic post “Don’t celebrate until the ink is dry and cash is in the bank”, on how you’re most vulnerable when you’ve almost won. (This has been my challenge. I tend to celebrate too early and lose guard.)

5. You have to observe patterns. You don’t have to calculate every move. There’s a bigger picture.

6. When in doubt, flip over the board and look at it from your opponent’s point of view. In business there’s not usually an opponent, but looking at things from a different viewpoint is very helpful.

(This originally appeared on my blog leonov.org)