"What has chess taught you that's useful beyond the game itself?"
For months, I struggled to answer that question. It took a bunch of conversations with friends, reading, and a lot of curiosity to land on something I feel good about. The answer, in its plainest terms, is that chess counterintuitively teaches you how to avoid mistakes.
It's very simple. People think that chess is a game of intelligence, but at its core, chess is applied math covered in strategy's clothing. It's a game of calculation, but also an exercise of maintaining a problem in your head. It's abstract thinking personified. Like a math proof, chess has an elegance and beauty to it. That's what chess is. What chess teaches you is not about its beauty, but about avoiding all of its mess.
Every beginner's journey in chess follows a familiar pattern. You blunder a piece, promise yourself you'll never make that specific mistake again, and then promptly blunder in an entirely new way in your next game. For most, this learning process is one of trial and error. You come up with new defensive strategies to protect against the next blunder. But all these strategies are insufficient for doing the thing you actually want to do—checkmate your opponent. So you continue to struggle through until it finally happens. You've played so many games, and seen enough positions to know how not to blunder.
What happens in the inbetween?
My best guess came to me after reading this line from a graduation speech given by Charlie Munger.
What Carson did was to approach the study of how to create X by turning the question backward, that is, by studying how to create non-X. The great algebraist, Jacobi, had exactly the same approach as Carson and was known for his constant repetition of one phrase: “Invert, always invert.” It is in the nature of things, as Jacobi knew, that many hard problems are best solved only when they are addressed backward.
The secret to making fewer blunders in chess is to realize that sometimes the goal is about proving yourself wrong, rather than proving yourself right. Most people can see a bad option sitting right in front of them. But most people struggle to disprove their own intuition. That's what happens when you blunder. You prioritize asking "Why is this move good?" over asking "What would make this move terrible?".1
In anything you do, you can transform the question "How do I create the best version of X?" into "What would cause X to fail catastrophically?" That's an extremely powerful frame to view pretty much anything. It puts you in a position of opposition long enough to see your own mistakes sitting right in front of you. And once you can identify your own mistakes, it leaves only the options which give you the best chance of success.
So, like with anything, the goal is progress, not perfection. Develop a habit of consistent constructive skepticism. You don't always have to be right, but you do have to be less wrong over time. In chess, business, and life, it's the difference between a win, and a lesson.
Glossary
blunder - To unintentionally give your opponent an advantage