As I've mentioned before (link to post here), I've picked up chess as a hobby since around April of this year. It's been a delight to have an activity I can do for fun just about anywhere, anytime. I think it's also been good for me to have something in my life that is purely for fun and not for instrumental reasons.

I've been pleasantly surprised how fertile the chess metagame has been. Historically, I have been — and still am — skeptical of the idea that board games teach transferable skills. But learning chess has been interesting because it's such an unforgiving game. Even if you build up a large advantage, if you slip up and make one mistake, you can lose a game instantly. And it is extremely easy to make mistakes, since virtually all games are played under time control to keep the duration predictable. Time pressure makes fools of us all.

I. Are You Thinking, or Pretending to Think?

The most stark lesson I've learned from chess is it teaches you what it's like to think hard. There's quite a bit of chess jargon out there, but a very useful term is "calculation." To "calculate" is simply to try to see several moves ahead: if I move a piece here, how will my opponent respond, then how will I reply to that, then how will my opponent reply, and so on. In chess, many move sequences (or "lines") are "forced" because of attacking pieces causing checks or threatening valuable pieces. In those situations, the only rational reply is to capture the attacking piece or make a move out of check. If you are able to predict the right chain of "forced" moves, you can calculate a few moves ahead and see whether, say, putting your opponent's king into check with your bishop in a particular position actually gets you closer to winning.

What chess reveals is just how reluctant we are to calculate, because it's hard work. Instead, the overwhelming temptation is to just make a move based off our "feel" of the position. Again, time pressure makes being lazy very tempting, but as John Bartholomew likes to say, "You can't think yourself out of a bad position." It sounds obvious, but it's much better to invest the time thinking to avoid getting yourself into a bad position, because once you're in one, there's typically nothing you can do other than hope that your opponent blunders a piece or two to let you back into the game.

II. Staying Cool

I touched on time pressure earlier, which brings up the psychological dimension of chess. It is an intensely psychological game, even when playing anonymous games against relative novices online. There are players who will be very aggressive out of the opening and force you into defending weak pawns that are left undefended (or only defended by your king) during standard openings. It is easy to start to panic when facing these attacks as a beginner, because it puts pressure on you to look for the correct move to defend, and if your opponent keeps the pressure up you feel like you're losing.

With enough experience, though, you learn to look for the "quiet moves" that fortify your position and prevent your opponent from continuing their attack. Often these quiet moves are found by stepping outside of the gun-to-the-head urgency of your opponent's attack, and looking for a simple move that will guard critical pieces. Often, the basis for these quiet moves is understanding that your opponent is overextending themselves with their attack and you can hit back if your reinforce your pieces well enough or make smart trades. Or a quiet move can come from cooly accepting that you have misplaced a piece and are going to be forced to lose it with little or no compensation. A good example of this is setting yourself up to lose a piece in a way that minimizes damage to your pawn structure.

Playing as the aggressor — with the "initiative" as the jargon goes — confers a psychological advantage in chess, since by definition you are leading, and your opponent is just reacting to your moves. But maintaining the initiative is difficult, because you have to come up with creative ideas to continue fueling your attack. Worse still is the temptation to continue your attack even when you don't have the right resources to finish it off. There is tremendous egoic inertia behind a big attack. To the untrained, voluntarily stopping short of winning feels a lot like losing. It's almost worse, because you have to admit to yourself that your idea wasn't as good as you originally thought. Which means you're stupid.

Unfortunately, you have to feel stupid thousands of times to get any good at chess. Chess is a brutal game. Since the rules are simple and it's a game of perfect information — all the pieces are on the board for both players to see — your losses are always your fault. You have to get comfortable with the knowledge that, in any given loss, no matter how brilliantly your opponent played, you could have avoided losing if you made a different move in a critical position. And, even when you're winning with a crushing position, you must never relax, or you may make a blunder that lets your opponent back into the game.

III. Ratings

With the wrong perspective, playing chess can become very not-fun because of the combination of the game's brutality and the rating system. Playing rated games is the default on the main chess sites. This is good because it ensures fair matchups. But because your opponents' skill levels scale with your own, on average, you will only ever have about a 50% win rate. As you get better, that win rate will improve to 55-60%. But that's still losing very frequently! And that 55-60% win rate only persists until you plateau at your new level and regress back to a 50% win percentage when you're matched up against opponents of your strength again.

The other problem introduced by the rating system is how every game has stakes. This is a good thing, as it incentivizes improvement. But losing streaks feel absolutely terrible — your rating starts diving, and you try to play more games while "on tilt" to make it up, which just results in more losses, and eventually you have to accept that, yes, for the past few games, you've been playing worse than usual. And the only way to play better is to move beyond the losses and focus on having fun again.

IV. Controlling Squares

It seems that every domain has some cliché about negative space. In hockey, Wayne Gretzky became The Great One by going to where the puck was going to be. In music, there's that saying (attributed to Claude Debussy) that music is the space between the notes.

Well, chess is no different. Chess is really a game about controlling squares, not about the pieces. Most basic chess principles are really about square control. Here are some examples:

1. Principle: control the center with your pawns. This one is self-evidently about controlling central squares - the most critical on the board: d4, e4, d5, e5.
2. Principle: place rooks on open files. Likewise, place bishops on longer diagonals. And finally, place your knights in the center. Again, this is about controlling as many squares as possible given how these pieces move. (How many squares a piece controls is called that piece's activity)
3. Principle: develop knights before bishops. In the early stages of the game, with more pawns on the board, knights can control many more squares than bishops can because they can jump over pawns, whereas bishops have issues with limited line-of-sight.
4. Principle: get your king to safety via castling ASAP. This reduces the king's exposure by confining him in the corner of the board.

You get the idea. Offensive force, in chess, is projected over board area. As the game progresses and pieces are moved, each player's arsenal is projected over a different subset of the board in response to their opponent's moves.

V. Blunderchecks and disciplined moves

I came across the neologism "blundercheck" on Timber Stinson-Schroff's substack.

A "blundercheck" is a mental habit that prevents you from making a blunder. A standard "blundercheck" would be scanning the board following a checklist prior to making any move:

1. Am I moving a piece that was attacked by my opponent's last move? If not, why not?
2. Is the square safe? (Not attacked by opponent's pieces, or properly defended by our pieces)
3. Does this move leave any of our pieces hanging?
4. Does this move us in range of a fork or other simple tactic?

If it passes the blundercheck, the move is ok to make (or at least, not a blunder).

Blunderchecks are good protocols to institute into your daily life. The most common is checking your pockets or purse for your keys, wallet, and phone before you leave home. Another is proofreading your emails before you send them.

But let's return to chess. Though the above blundercheck is so simple and easy to remember, it is very hard to have the discipline to carry it out after every move. As I said earlier with reference to calculation, it is overwhelmingly easy to take the path of least resistance and play the first move that comes to mind. It takes mental discipline to force yourself to apply rigorous thinking to every move, especially when the clock is ticking away in the background.

VI. Board Vision and Cognition

One of the other ways that chess is like sports is that skill depends on your vision: your ability to see plays develop. Beginning players get tunnel vision and just focus on one move at a time, parrying individual threats and not thinking about the rest of the game.

Many basic tactics, like the discovered attack, where a piece is able to attack another piece because a third piece that was previously blocking its line of sight just moved, are by definition hard to see unless you know they are possible, so you scan the board for them.

The worst feeling in chess is to be surprised by your opponent's move. If you didn't see it, then you were not observing their threats carefully enough.

Chess has proven a useful — if humbling — monitor of my cognitive abilities. Later in the week, as sleep debt mounts, I am not able to see the board as well and miss obvious moves. Just trying harder or going slower helps some, but I still miss clear threats. Over the weekend, after catching up on sleep, I see the board much better and go into autopilot less. Playing the right move is just easier when I'm well-rested.

This reinforces a hard truth about not getting enough sleep: you can't even tell that you're cognitively impaired. It's ironic that I picked up chess because it was something I could do while taking care of a baby, but now that I'm invested in getting better, I don't like playing late at night or when I'm distracted because I'll blunder and lose games. Instead of playing games, I'll queue up a youtube video or tactics puzzles. This gives me the practice I need while not putting my rating at risk.

Moving forward, I expect to get even more choosy about when I play games. The tricky part is that playing a lot of games is necessary to improve, so you can't get too attached to your rating. I've set a goal of achieving a Lichess 1500 rapid rating by May 1 2026, which is about after 1 year of playing. This is the median rapid rating on Lichess. That should enable me to be competitive with some friends I know who play chess regularly online, and sets me on the path to being able to play over the board tournaments as I improve further, which is my true long-term goal.