Even a Dumb Plan Is Better than No Plan at All

Or: don't invade Russia in the winter.

A couple weeks have passed at the ol’ chess club. Two weeks ago, I won a nice match against a 1782, but as is more my style, I want to focus on the loss I sustained last week against a 1780. (My rating currently stands at 1631… but who’s counting!¹)

A Position.

Black to play. Both sides have some advantages and disadvantages: I’ve successfully messed up White’s pawn structure on the kingside, but he has a passed pawn on d5 as well as the bishop pair. However, that passed pawn is also isolated, and I have it blockaded with my bishop. It could be a target.

Much of my play up until this point had been centered around enabling the c5 pawn-break, and that had been enough to get me to not just an equal position, but one with real winning chances. However, after playing c5 and completing my plan, I found myself basically… aimless. I knew I had the asset of that direct path to White’s king down the g-file, but I didn’t know what to do with it.

I’ve written about this kind of situation before, under the heading of, “What do you do when you don’t know what to do?” But this is one of the things that I love about chess: the same kind of situation can present many different dilemmas. In that case, the choice was between flexibility and commitment. Here, it’s a bit more open-ended. No move necessarily presents itself as a point-of-no-return. There’s a larger question at hand: what am I hoping to achieve from this point forward? What’s my plan?

Let’s go back to my analysis of the position. From my perspective, I have two assets to work with: Black’s broken kingside, and his isolated pawn. So it makes sense to formulate a plan based on one of these two things.

Well… attacking the pawn seems easier, doesn’t it? Just gotta have more attackers than he has defenders. Simple math. And wait: if I capture his rook, and he takes back with his rook, then… can’t my knight just pick up the pawn? Then I’ll be a pawn up! Victory will be mine!²

A Lesson.

There are many different opinions on how chess players should improve, but one of the most agreed-upon approaches is to focus on tactics. At the far end of this idea, you have Richard Teichmann saying in the early 20th century that “chess is 99% tactics,” the sense being that, if you can see how to take your opponents’ material, then you’re ultimately going to win the game more often than not.

The problem with this approach is that, when you train tactics, you know that you’re training tactics. If you do puzzles on chess.com or Lichess, or from a puzzle book, you look at a position and understand that you’re searching for a tactical motif; often, you even know the kind of motif you’re searching for.

Real chess isn’t like that. In real chess, the goal isn’t to find and play the tactic: it’s to win the game. If you approach a chess game as if it’s a tactical puzzle, then you’re going to try to identify a tactic no matter what — even if there isn’t one. It’s a classic “if you’ve got a hammer, everything looks like a nail” situation.

Don’t get me wrong: tactics are super important. Think of them like your basic quarterback skills: accuracy, arm strength, mobility. But just like how a good pro day doesn’t equate to a good NFL quarterback — *cough, Zach Wilson, cough* — raw tactical skills don’t necessarily make a good chess player.

When I showed my game to my higher-rated and more-experienced buddy Christian afterward, he made an observation that never occurred to me over the board: “As you probably know, when playing against the two Bishops, trade one of them off and steer game to good N vs. bad B. Be5 is the move there, with the idea of cancelling that (potentially) monstrous Bishop on c3. After ... Be5, you're certainly not worse, and I'd rather be Black owing to White's busted structure.”

What Christian is describing is a plan. It takes into account the imbalances on the board and responds accordingly. It offers a flexible path forward, one that can be pursued even if the next move or two don’t work out perfectly.

On the other hand, laser-focusing on winning the d5 pawn tactically was not a plan. Do you know why?

Because I wouldn’t have been able to tell you what would happen after I won the pawn. How would White respond? How would I respond to White’s response?

I’ve written about this before, but, contrary to popular belief, the measure of a chess player’s quality isn’t how many moves ahead they can see: it’s how well they understand the position on the board. If you understand the board, then you know what you should be trying to do, and you know what your opponent should be trying to do, and you work to do what you’re trying to do earlier and better.

My thinking, by contrast, started and ended with “capture the pawn,” operating under the assumption that “going a pawn up” could only be a positive result. So I played Rxe1, watched with pleasure as he took back with the rook, and then pounced, hoovering up the pawn with Nxd5.

Unfortunately…

White has Be4. This pins my knight to my rook. I lose the exchange, and while it isn’t quite game over, White now has the clear edge.

Instead of coming up with a plan, which required me to think longterm about the position and understand the situation’s ability to fluctuate and evolve, I looked at the board like it was a tactical puzzle that I could solve. And I lost because of it.

Compare this to my earlier play, when I had been focused on the c5 pawn break. This was what you might call a dumb plan, in that I wasn’t sure exactly what I would do after I played the pawn break. But I knew that it would relieve the pressure on my position, create space, and make my pieces more active.

Now, when I say a dumb plan, I don’t mean a bad plan. A bad plan would be invading Russia during the winter. A dumb plan is more like a dumb phone: it works, but it just doesn’t have as many capabilities and features as a smart plan / phone. Christian’s plan was a smart plan, in that it would have permanently rectified an imbalance and shifted the dynamics of the game in my favor.

Bad plan.

To further drive home this point, here’s an anecdote from my professional life. In 2017, I was a senior editor at New York magazine. Good job. But I was ready to take another go at film and television, in which I had briefly worked in 2013, when I moved to Los Angeles to be a writer on the then-launching network Fox Sports One’s flagship show, Fox Sports Live.

I managed to get a small gig writing a quirky 45-minute TV mockumentary about the Pine Tar Incident. At the same time, I was told that I would be brought on to work on another project that was about to be commissioned by a major streamer. Confident that I had now secured for myself a burgeoning career in Hollywood, I departed New York.

Within weeks, that streamer project collapsed, as they so often do, though I didn’t understand that at the time. In reality, I had left my steady job at a major magazine for about eight weeks of work. Once I finished it, I found myself functioning largely as a journalist again, except now I was freelancing instead of holding a very desirable staff job.

I had looked at my life like it was a one- or two-move tactical puzzle that I could solve — and when I got the answer wrong, I found myself in a tough position. The fact that I eventually turned things around doesn’t change the fact that I mishandled the situation. Whereas if, at the time, I had forced myself to come up with a plan, however dumb, I would have had to face the reality that I might not get the second job, which would have led me to consider whether it was truly worth leaving New York at that time, or whether I could have carved out some middle ground.

So: make plans, dumb or smart. Don’t invade Russia in the winter. And train your tactics, but remember: a real chess game isn’t a puzzle that can be solved, and neither is LIFE.

1. Me, I am

2. If he takes back with the bishop, then that piece gets way less active and I can take over the e-file with my other rook. So that’s also good. In fact… it would have been way better for me, but I didn’t know that yet.