What Do You Do When You Don't Know What to Do?
Or: Will Kevin Lose to Another Child?
Another week at the chess club, another showdown with a kid.
But before we get into that, a quick housekeeping note: I’m going to try something a little different this week. I’ve done the deeper chess analysis as a video. (I guess I’m a streamer now: given a long-enough time horizon, we’re all bound to stream eventually.) There are a few reasons why:
It should make the newsletter a bit more readable, for the chess aficionados and non-players alike, and prevent it from ballooning to Tolstoyan lengths every week.
Even chess fans have gotten used to watching video analysis versus reading written-out lines.
It seemed like fun!
So if you have any curiosity about chess the game, and aren’t just here to see me get humiliated by children week after week, I’d encourage you to give the video a try even if you skipped the chess analysis last week — hopefully it’ll help people understand the game a bit better.
Also: welcome to the new subscribers! It’s very cool to see people signing up for this, and I’m hopeful that you’ll stick around and spread the word. I’d love to build a community here. If you HAVEN’T subscribed yet…
And one more thing: I’m ktlincoln on chess.com. Feel free to hit me up if you want to play!
*clears throat*
Back to the main event. For the second week in a row, I was paired up with a tween who had hundreds of rating points on me. In this case, however, she was rated 1832, a little under a hundred points below last week’s opponent — and I had played her before.
The last time, she beat me, and as soon as I resigned, she preceded to reset the board and show me exactly where I could’ve pulled off a nice tactic that would’ve given me an edge. If an adult had done this to me, it might have come off as condescending at best, and psychotically aggressive at worst. But coming from a preteen, it was weirdly endearing. Thank you for believing that I can still improve in my senescence!
So: could I redeem myself against this child? Or would she once again take me, the old man, to school?
A Position.
Things started off well. This position came up 11 moves into the game. By this point, I had taken nine minutes to play my first moves; she had taken 34. Chess players at our level have generally done a fair amount of opening prep, and I’d managed to get a line that I knew and she didn’t, so she had to put a lot more thought into her play, whereas I could proceed almost automatically. But my last move hadn’t been the best, so the engine has this as a pretty much dead-equal position.
The crux of the matter is that she has pressure on my d-pawn. If I don’t do anything, she can trade her bishop for my knight on f3 and then take with her knight, earning not just a pawn, but a tempo on my queen. I can’t allow this to happen.
That means I essentially have two options: I can defend the pawn with one of my pieces (bishop, rook, or queen) — a temporary measure that can be interfered with, but also allows me flexibility.
OR: I can play e3, defending the d4 pawn with a pawn — solidly securing that pawn, but locking in my structure.
Which is better?
A Question.
Here’s a question: what makes a chess move “good” or “bad”? This might sound banal at first, but the complexity at the heart of this simple concept is arguably the main reason why chess is so compelling to sickos like me, and it’s a big part of why I’m writing this newsletter: I want to better understand why my moves are good or bad.
If you’re watching most sports, you don’t have to be a head coach or former D-I player to know when a sequence is good or bad. A team either gains or loses yards. They either score points or fail to score points. They either retain possession of the ball or surrender possession of the ball.
Most sports are almost shockingly simple in their construction: retain the ball and put it in the place you’re supposed to put it. Every game is composed of a series of these events, and whichever team fares better in more of them tends to win. There’s no ambiguity about most of these steps on the way to that end result; it’s not like there’s any situation in which a quarterback throws an interception, or a point guard misses a shot, or a hitter strikes out, and you’re like, “No, wait, this is actually good.”1
Individual sports are no different. In tennis, you either return the ball or you don’t. In golf, you either get closer to putting the ball in the hole, or you get further away. In racing of any kind, you either get to the end fastest, or somebody else does.
Of course, this doesn’t make these sports devoid of complexity — many of them are very complex in how each side tries to achieve the agreed-upon objectives. (See footnote #1.) But it is also true that, at any given point, both teams know exactly what the other is trying to do.
Chess is not like this. Yes, each player wants to take the other’s pieces and checkmate the king. But the vast majority of the moves in any given game involve neither of these actions. For some, the almighty engine has obscured this truth. It’s part of why the Great Eval Debate rages so hotly in chess circles. Yes, the engine can tell you if a move is good or bad. But even then, you have to see why. You need to understand what it is that the move does that is good or bad. Does it take space? Does it improve your structure? Does it activate latent threats? The engine won’t tell you. It just flashes a number. That number means nothing if the player with an edge doesn’t understand why they have an edge.
If you want a great example of this, just look at the World Championship that’s happening right now. I have followed many of these games, and I often have no idea why either player is making the moves they’re making; in fact, some of them look crazy to me, because they’re happening at such a high level that they defy the rules that most normal players base their strategy around. And I’m not alone — the GMs watching also don’t always know whether the moves are good or not.
Thinking along these lines, you could make a simple statement about a chess player’s quality: the better a chess player is, the clearer they can understand whether a move is good or bad.2 Chess is interpretative. It’s intuitive. It isn’t quite subjective, but subjectivity is essential to objective success in it. In that sense, it’s almost like music. Yes, we all generally agree on what is good or bad music, and there are even objective qualities that good music often has — but great musicians just know when a musical choice is good or bad, in a way that seems almost magical to mere mortals.3
I’m explaining all this because I think the move e3 illustrates it quite well. This is a bad move, but at no point before playing it did I think, “This could be a bad move.” I thought it had its drawbacks: it takes squares away from my own pieces, namely my bishop, which has been deprived not only of e3, but of the squares behind that.
But I’m protecting the d4 pawn! And my bishop is over-protected, too! How bad could it be? I’m just moving a little PAWN!
The answer: it could be very bad. Very bad indeed. And as soon as I made it, my young opponent proceeded to wipe me off the face of the Earth.
The best thing you can do in chess is play “forcing moves,” i.e. moves where your opponent pretty much has to react in a certain way: this takes away half of the game’s difficulty, which is in guessing how the other player will respond to you. This is much easier to do when your opponent has fewer squares available to them, and less options for what they can attempt. By closing my structure, I had very few possible responses when things began to go wrong — and two moves later, I missed the only serviceable move, catalyzing a rapid spiral.
If you want to get deeper into the CHESS of it all, here’s the video I recorded analyzing the game:
But TLDR — my extra 25 minutes on the clock didn’t matter: the game was soon over.
So: I made a bad move. But is there something about the type of move that it was that made it more likely to be bad? After all, before I made it, I had correctly judged that I wasn’t in a critical position, and that my opponent and I were basically equal. It turns out that I had many good moves that would’ve kept the game even — and I didn’t choose any of them.
In this sense, chess is very much like life, and more so than most other sports, where the score is clear and everything is measured. While most of what we do in life is oriented toward a certain goal — get a great job! lovingly parent your child! be cool! — the steps on the path to achieving these goals are often maddeningly murky. If I wear this jacket, do I look cool? Or do I look like I’m trying to look cool, which is decidedly uncool?
Last week I talked about how, if I’m going to beat players that are better than me, I can’t count on getting lucky. This week serves as a nice development of that theme: if I’m going to beat players who are better than me, then I need to get out of non-critical positions without shooting myself in the foot. Which means: even more important than making the optimal move is making a move that doesn’t hurt me. As my friend and collaborator Julien Smith messaged me during our current game on chess.com, “I realized something: basically getting better at chess is just being patient, making solid moves, and waiting for the other guy to make mistakes.”
Yes!!!
Which leads us back to the headline of this newsletter: what do you do when you don’t know what to do? When you have to make a choice, but you don’t know what the right choice is? In chess, or in life? How do you minimize your chances of making a bad choice?
Hell if I know. But taking this chess game as an example, I can make a humble suggestion. There are four moves that would’ve kept the game more or less equal: moving either rook to d1, moving my bishop to e3 (ugly, but it works), or exchanging pawns on c3.
What do these four moves all have in common? They are flexible. When I play e3, I “close the structure.” Pawns are the only elements on the board that can’t move backward, so when you move a pawn and create a chain of them, you’re solidifying the way the board is arranged at that time.4
By closing the structure, I am committing myself to it. There’s no going back. I’m saying, I like the board this way, and I want to play this kind of game. But I wasn’t trying to say that. I didn’t actually like the look of this structure all that much. I tried to solve a temporary problem, a threatened pawn, by making a permanent change — whereas if I had tried a temporary solution, i.e. moving one of my pieces to defend the pawn, I would’ve been better off.
A lesson begins to rise up out of the fog of getting destroyed by a child: when you don’t know what to do, make a flexible choice. Ideally, this choice will still fit into whatever your larger plan is. Ideally, you have a larger plan. Plans are too big of a subject to get into now, but suffice it to say that I did not have a good-enough plan in this game.
Now, this is a helpful realization for me, a heuristic that I can apply to future chess games — when I’m uncertain of how to play, I can err on the side of making a move that leaves me some flexibility. Moving a piece instead of a pawn, for example.
But I suspect it makes sense as a larger thought process that could be used in other sports, or in life as well. I’m thinking, for example, of the New York Jets — the team that tormented me throughout my childhood, and toward whom I still experience pangs of relapse every so often. When they signed Aaron Rodgers and built the team around him, they fully committed to one pathway toward success. This didn’t work when Aaron Rodgers got injured. However, it also didn’t work when Aaron Rodgers didn’t get injured, as this year is demonstrating.
Would the Jets — would NFL teams in general — be better off making roster decisions inclined toward flexibility than massive and long-term commitment? Compare the Jets to the Detroit Lions, who are the best team in the NFL despite being the most injured. The Lions are a well-rounded team. The Jets are not.
Or: compare the Jets to the Philadelphia Eagles, who have repeatedly spent their draft picks on the most high-value positions regardless of the personnel they already had, highlighted by the decision to draft Jalen Hurts 53rd overall in 2020 even though Carson Wentz seemed set as the starter. The Eagles are currently 11-2, and they’re about to make the playoffs for the fifth-straight year.
Now, if Rodgers had played like MVP-level Rodgers, could the Jets have been great? Possibly! But, and this is the key point, the fewer pathways toward success that you give yourself, the less likely it is that you’ll be successful. And the Jets absolutely needed Rodgers to play like an MVP-level quarterback to be successful, despite their being plenty of indications that he might not.
Without quite realizing it at the time, I experienced a similar version of this in my own career. When I began working in the film and TV industry, I assumed that the projects I was attached to would, more often than not, work out. I quickly — very quickly — learned that this was not the case: in Hollywood, it’s more common for projects to not make it to the production stage, for any number of reasons. And if they don’t get produced, you usually don’t make any money.
I had thought that the important thing was to commit: to go all in on being in film and TV. To signal to myself and the universe that I was serious about it, that I was all in. And I think this is a message our culture feeds us quite often: we romanticize the big risk, the taking of the leap, and we imbue the leap itself with virtue, as if you’ll be rewarded for the moral quality of that commitment.
I think there’s some truth to this idea; when you attempt to do something, you have to make a serious attempt, and that means dedicating resources to it, whether those resources are time or attention or money or whatever. But, at least in my situation, I soon realized my mistake; my assumption that things would work out soon turned into a more realistic appraisal of the odds. So in response, I first broadened the slate of projects I was taking on, making more and more bets, and then eventually I also added another skillset that I could use to find work when the film and TV stuff was slow.
Now, I have a career that I’m feeling really good about, and while I’m sure I’ll have to course-correct a million more times over the course of my life, I can safely say that flexibility and versatility is a big part of why I feel good about it. I’m certainly not alone in taking this approach.
I had never made this connection to chess before. But seeing it now, it feels blindingly obvious, and I’m excited to try to apply it in my games to come. I’m curious to hear if it resonates with anyone reading, and if flexibility has served you well — or if you’ve done better by making moves that you couldn’t back away from, increasing the risk of failure but also decreasing the chance that you’ll abandon ship. Let me know!
Also, tune in next week, when it looks like I should be playing someone closer to my skill level — meaning that this newsletter could have a very different tone, depending on how that goes!
WATCHING / READING / LISTENING
As promised last week, I want to share some things I’m watching, reading, and listening to, as befits my inveterate culture-writer background.
WATCHING: English Teacher, FX. As new parents, “half-hour comedy” is really about as much as we can generally handle most nights — hence why we’ve watched four seasons of Veep in the last two months — and this show happens to be genuinely funny, which is all I’m ever really looking for from TV.
READING: Devil House, John Darnielle. I’ve been listening to the Mountain Goats since high school, which means I’ve become very familiar with John Darnielle’s distinctive voice and his wild stories about the best ever death metal band out of Denton and the worst relationship ever. But this is the first of his novels I’ve read, and so far, I’m impressed — it’s a well-written and thorough exploration of true-crime psychology, while also demonstrating the immense empathic powers that characterizes Darnielle’s songs.
LISTENING: Mahashmashana, Father John Misty. There has yet to be a Father John Misty album that I didn’t like, but Mahashamashana really achieves peak Misty — witty bon mots, epically long story-songs, deceptive depths of feeling — while also adding some new sonic wrinkles to the equation (the swagger of “She Cleans Up,” the eruptions of “Screamland”).
Now, you could make the argument that this is an oversimplification: obviously, the stats revolutions in baseball and, more recently, soccer have demonstrated that, for quite a long time, people had no idea what actually led to success in those sports. (See: Moneyball, by either Michael Lewis or Bennett Miller, and Net Gains, by the patron saint of this newsletter, Ryan O’Hanlon.) But I still think there’s a massive difference between the experience of watching a baseball or soccer game for the average fan and that of watching a high-level chess match: ambiguity is built in to the experience of chess, whereas when you’re watching baseball or soccer, there’s still a score that tells you who’s winning and who isn’t, and when the timer goes off, the team that’s winning wins.
This is, of course, closely related to the statement I made about the quality of a chess player last week: “How good you are at chess exists in direct proportion to how well you can read the meaning in [a] position.”
It’s no coincidence that, as George Steiner points out, two of the three areas of human endeavor where there have been genuine child-prodigies are music and chess. (The third is math.)
Now, this isn’t permanently closing the structure, as I could have eventually made a break for e4 with that same pawn, but at least in this moment, I’ve closed it — and that’s all that matters, because, as I mentioned last week, a chess game at any given move is only what it is at that moment: it has no future and no past.