Strategy
What Chess Teaches You About Decision-Making
“The map is not the territory” can serve you in many cases
You have two good moves, which one do you make?
You have two potential career paths, which one do you take?
I was 7 when I faced for the first time the struggle to make a rational decision. It was on the chessboard.
“Should I move the pawn or the knight?”
“Should I move it to this square of that square?”
It was painful to watch.
This type of question has been haunting me for years as I continued to play the game of chess and the game of life. Mistakes made and lessons learned.
It starts with the chess position
In chess, every setting, or as we call it “position”, is different. It’s unique until someone starts playing it. But then it can easily lead one to another unique position.
Imagine fighting in a desert on ice, or fighting at the North Pole on the sand. The environment looks familiar, but the territory is new. Based on familiarity, you can assume that you can instantly use prior knowledge to make decisions. This happens often, and it’s most of the time misleading.
Similarities and differences
In chess, a knight on a different square can drastically change the chess position.
Look at this position, and then at the next one. Can you spot the difference?
The White Knight that was moved from the g square is the difference. In Position A, it’s on the e2 square and in Position B is on the f3 square. For someone new to chess it would look like a minor detail, but for a chess player it means everything.
This change can easily lead to coming up with a new plan, and a new strategy.
Chess players do not see the chess board in pieces and squares but in interactions and opportunities. That means each piece is not siloed, it shares the space with all the other pieces. When the Knight moves to a different square, it creates a new dynamic: it may take the place of another piece (e.g. in Position A, it takes the space of the f pawn), provide strength to its pawns, and create future threats in the opponent’s position. These are three changes at once, if not even more.
What chess teaches you is that every single detail matters, and you have to take any change into account.
Going back to humans, we prefer generalizing and we look for patterns. Why? Because patterns make us feel safe. Patterns bring balance and avoid contemplation, which is essential for decision-making. According to Kahnemann (the author of Thinking, Fast and Slow), this would be called fast thinking.
Fast thinking vs. slow thinking
Fast thinking is emotional, automatic and highly error-prone. Fast thinking relies on generalization and happens involuntarily. If you are a good chess player, you could rely on your fast thinking and make a move instantly, because you have seen this position before. If you have not seen this position before, generalization might lead to problems. You might need some seconds to realize that the position is different and to come up with something new. For that, you would need slow thinking.
Slow thinking is activated when you start questioning an action or an event. You bypass the auto-pilot and use rationality instead. This happens when you stop to double-check your auto-pilot chess move, and then make a more considered move; or you just have no idea and start searching for other moves and analyze each one of them.
Slow thinking is mostly used in complex situations. Chess is a rather complex game and it teaches everyone who learns it to stop, contemplate, and question everything.
Make a decision the right way
Each move represents a decision. You seek possibilities, analyze them, and choose one. From what we have seen so far, it mostly avoids generalization. Generalization looks safe short term but it’s not in the long term. You can find good moves with generalization, but you will never understand the rationality behind them because you did not give yourself the time to do that.
You think you want to make good decisions, but what you really want is to make decisions the right way.
Each move creates a new problem, so remember you have to reset your understanding of the position. Could it be that the Knight is now on a different square?
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