What Are My Options?

The most helpful chess technique for real life

This will be a shorter post than usual, as I’m writing from the lobby of the Parsippany Hilton. I’m here for the US Amateur Team East. If you’re here, stop by the Hilton hotel bar after the last round on Sunday for a meetup with me and Ben Johnson from Perpetual Chess.

I’ve always thought the applicability of chess to real life is somewhat overblown. I mean, think of the chess players you know – are they all succeeding wildly at life? But there’s one technique that I’ve found equally helpful in chess and life, and that’s the idea of candidate moves.

The core idea is to explicitly list the options you’re considering before getting deep into analysis. This helps clarify your options and avoid the situation where you spend a ton of time analyzing a complicated sequence, when there was a better, simpler option available.

I don’t use this process explicitly for every move or decision. When things are going well, it can be faster and easier to operate more intuitively. But where it really shines is getting unstuck.

In chess and life, indecision often results from a mismatch between expectations and reality. Often, we have a general sense of how good a situation ought to be, and a corresponding feeling we want to get from making a decision. When none of our options give us that feeling, it’s easy to fall into a pattern of cycling through them indefinitely.

For example, you might feel like you should have a winning attack, but none of the aggressive options you can calculate leads to a win. Or you have an email you’re dreading to send, but none of the ways of phrasing it makes it any less terrifying.

Cycling through the same options is usually a waste of time. It’s rare that the same option gets any better the third time you look at it.

This is where the candidate moves technique is really helpful. The idea is to explicitly list the options you’re considering. In real life you can write them down. In chess this is against the rules, so you just have to try to list them quite clearly in your head.

If none of the moves you’ve identified so far appeals to you, it’s not a bad idea to brainstorm for more options. In chess the most costly and common calculation errors result from missing an option on the first move. Sometimes you can identify a hidden option that brings the evaluation of the position in line with what you were expecting.

But other times, there are no better options, and you have to accept that the spot you’re in isn’t as good as you were expecting or hoping. In this case, explicitly listing the options helps you come to terms with the new reality.

Usually, the worst mistake is to make no decision at all. While you may feel the situation is worse than it ought to be, if you choose the best of your options, it’s also usually not as bad as you feared.

The game develops in unpredictable ways and usually there’s at least one opportunity to save a draw or a win. You have a better shot at seizing this chance if you didn’t burn all the time on your clock looking at the same crappy options over and over.