When I was a teenager, I was notorious at the Atlanta Chess Club for getting into time trouble. I’d play a game with 30 minutes per side and struggle to not lose on time, eventually forced to blitz out a flurry of moves without thinking as the final minutes and seconds slipped away on my clock. This same problem persisted at longer time controls too: 45 minutes per side, 60 minutes per side, 90 minutes per side, even three hours per side—I’d still run short on time!
I was paralyzed by indecision. In many games I’d end up in a difficult position where there were several reasonable moves to make, but I couldn’t foresee exactly what would happen if I chose one. Oftentimes I felt something better would come along if I waited and analyzed the board a bit longer. I’d tell myself that I was doing the right thing by patiently investigating the position more deeply, but more often than not I would spin my wheels retreading the exact same analysis I’d already done. After a certain point, there were rarely any new insights.
In retrospect, I realized this was just a way to defer making a decision since I didn’t have confidence in my ability to make one. As long as I don’t move, I haven’t made the wrong move. As long as I don’t move, I can still find the perfect one.
In the end, I’d burn a bunch of time, panic, and finally throw out a move that was no better in quality than the move I would’ve made if I had spent two minutes thinking instead of twenty. But now I had less time remaining for the rest of the game. In some cases, overthinking led to even worse decisions after I’d start seeing phantom threats and miss obvious ideas due to tunnel vision1.
I only resolved this problem many years after I quit serious competitive chess. Other life circumstances forced me to become comfortable with ambiguity and realizing that:
a) human beings are well designed to adapt to new circumstances and solve new problems and;
b) there’s actually a fun and joy in the unpredictability of the tree of decisions.
Since I can’t avoid the unknown, I’ll instead choose to relish the excitement of what’s out there — it could be bad, it could be good, but either way it’ll be different and an opportunity to solve new problems2.
I’ve also worked on letting go of past states. For example, if I was winning a game and then made a terrible move that brought the position back to equal, I’d get tilted and inevitably make more bad moves and lose. But if I had just been dropped into that position with no prior context of previously being in a winning position, I would’ve been fine; it’s an even game. Nowadays I’ve cultivated an indifference to abrupt changes in game state. If the flow of the game changes, I don’t get upset or thrown off balance. I reorient myself to the current situation: it doesn’t matter where we were, we’re here now and our job is to find the best move.
If you make a decision and commit, don’t you risk the sunk cost fallacy of charging ahead even when the facts and environment change? One subtle and underappreciated characteristic of strong chess players is their ability to adapt. They’ll make moves that improve their positions and proceed with their plans, while maintaining maximal flexibility to pivot to another plan if circumstances on the board suddenly shift.
Similarly, you can optimize for flexibility by creating the maximum number of offramps for each decision. At each offramp, assess the situation as if you were just dropped off at that point with no prior effort or context on what it took to get there; you want to avoid the inertia of automatically continuing down your path.
Right here, right now, does it make sense to take the offramp or stay on the road?
You won’t be able to foresee the consequences of every decision, so enjoy the fun of the unknown instead of haranguing yourself with what-ifs. Whatever you choose will inevitably pose challenges (and good surprises too!), so roll up your sleeves and make the best moves you can instead of mentally teleporting to the counterfactual universe of another choice you could’ve made. Don’t deceive yourself into thinking you can just stand there and endlessly ponder the options. Indecision is still a decision, and all it leads to is time trouble misery.
Footnotes
- Chess players have an aphorism for this: Thing long, think wrong.
- I just returned to serious competitive chess after over a decade away. And while I’m not (yet) as good a player as I used to be, this appreciation for the unknown has already drastically changed the nature of my play — my games are far more creative, dynamic, and exciting than my old games.