I Played Chess Every Day for a Year
Unbeknownst to me at the time, spring of last year was the twilight of my youth. During the intervening year, I have aged three thousand lifetimes. I am Gandalf the White without the wisdom. I am Baby Yoda, but hideous.
What happened? I’ll tell you: a cunning and malignant force hath turnt me into a desperate junky. “It’s just a way to relax,” I reassure my wife each night, my crazed eyes darting to and fro above the blazing-white glare of my phone’s screen. “Oh,” she sighs, “right.”
No, I did not become addicted to sniffing glue (although I am open to experimentation someday). Nor am I one of those… Candy Crush people. Nay! Worse. I became addicted to chess. And because I know full-well that chess has added nothing of value to my life, I am writing this blog post in a vain attempt to rationalize the hundreds of hours I’ve spent playing over the past year as if they weren’t a total waste of time.
So, it is with a heavy heart that I offer you three lessons I’ve learned playing this god-forsaken board game:
Lesson 1: Success is mostly about not making mistakes
The reason chess is such a disgustingly masochistic endeavor is that almost every game is decided because one player makes a mistake and the other player capitalizes on it. Often, a single “blunder” will so deeply imbalance the game that you practically lose on the spot. A very common pattern at my level is that one player will be winning for the first 20–30 moves of a game and then get instantly and unceremoniously checkmated after overlooking an obvious threat. An even more common pattern is that both players completely overlook their opponent’s constant stream of blunders and the game drags on like two chimpanzees lathered in Crisco wrestling each other to the death inside of a giant motorized hamster wheel.
Typically, the better chess player is not the more inventive or strategic — they’re simply the one who screws up less often. I’ve come to believe that this principle is true of successful people in most fields. Outsized success tends to come after a pattern of smaller successes that are rarely talked about, and no matter how far along someone is in their career, one big mistake can take it all away in an instant.
Lesson 2: Chess rewards opportunism
I‘ve started watching high-level chess players stream their games (yeah, I’m that deep into this thing). One thing I’ve noticed is that they almost never do what they say they’re about to do. “My plan is to push this pawn forward and attack his center,” they’ll say assuredly, and then proceed to go 10 moves in a row without touching that pawn. The reason is simple: the best players are constantly reassessing their plans and reacting to their opponents’ moves. Chess is a series of rapid-fire puzzles; it’s almost better not to think of the game as a sequence of related positions, but rather to assess each position in a vacuum. Bad players, like me, will come up with an idea and find themselves unable to let go of it. But if presented with the same position out of context, we might see a completely different opportunity that is glaringly obvious — perhaps an opponents’ threat or a tactic that just became possible.
I think a popular misconception about chess is that it’s a game of strategy when it’s actually a game of (mostly) impromptu tactics. I take some comfort in this aspect of the game. For as long as I can remember, I’ve felt intimidated by others’ confidence in the future. A task as simple as making “annual goals” can feel insurmountable to me — how can I know now what is going to be important in three or six months? Chess is similar; obsessing over a longterm strategy will only obscure the tactic hiding in plain sight. Instead, for most players, you should simply aim to prepare by getting all of your pieces in play and only allow yourself to strike when an opportunity presents itself. Eventually, it usually will.
Lesson 3: Move order matters
Some of the best advice I’ve heard for beginning chess players is to learn to visualize a sequence of moves and then try them out in different order in your head. Sometimes, you may think you can win the game with a clever sequence of 2–3 moves. But a classic beginner mistake is to start by using the wrong piece to capture your opponents’ material, giving them an opportunity to strike back with a counter-attack that allows them to squeeze out of trouble unscathed. For this reason, finding the most “forcing” moves that simultaneously advance your cause and limit your opponents’ options is a useful concept. Comparing the outcomes of a tactic if you change the move order is a fun and escapist element of chess playing. For me, calculation is the most addictive element of the game and has the benefit of a built-in (and almost-instant) feedback loop, sort of like if Sudoku squares buzzed when you filled them out incorrectly and dinged when you were right.
Chess is flamboyantly artificial — it would be a lot more like real life if your opponent were allowed to puke on the board or hold an air horn to your head while it was your turn or announce victory after the first move. But the core concept of move order is still useful as a framework for improving how you spend your time. For instance, if the first time you reach out to a journalist is to pitch them a story…you probably got the move order wrong.
Take it from me: don’t play chess. After a year of obsessing over it, I am still an objectively terrible player with nothing but this blog post to show for it. But if you do decide to play chess, at least play it with me.