Where’s the Win?

You’re better, but you don’t have a clear winning plan. Where’s the win??

That’s where grinding comes in play. You have to grind the most you can out of the position. Grinding is not only about you finding a win, but it is also about tricking your opponent into letting you win.

The chess book which probably had the biggest influence on me in this department was Endgame Strategy by Mikhail Shereshevsky. I read it when I was around 1800. It is an excellent read, and I highly recommend it.

If you could only learn how to grind just by reading a book or two… that would be way too easy. Grinding takes practice, skill, and most of all patience.

One thing I can relate to well is how not to grind.

  • Try too little – giving up early
  • Try too hard – essentially trying to find a forced win, not accepting a position with excellent winning chances, and doing something totally stupid instead.
  • Prematurely forcing events

Then how to grind?

It depends on how much help from your opponent you need. If you don’t need much and you have a winning plan, go for it!

Naturally, it is harder when you need help from your opponent, and I’ll spend most of this article talking about those kinds of situations.

First of all, in principle you should always calculate the most forcing line(s). If they aren’t too promising or you feel you may have something better, discard them for the moment and look elsewhere.

“Do not hurry”. That’s a phrase you will see over and over again in various chess books on the theme of the grind. Repeat the moves. Dance around. Improve your position.

When I first started studying the games of Capablanca, Karpov, etc., I was confused by all this stuff. What good does repeating the moves do?? You just get the same position you had a couple of moves ago. And dancing around is overrated. The author says Karpov played so amazing, blah, blah, blah, but he was just dancing around doing nothing. If it only weren’t for his opponent’s mistake, he probably wouldn’t have won. This is a rip off!!!

Soon enough, I learned the logic behind this. The hard way.

Imagine yourself in the shoes of a defender. You are worse, and instead of trying to finish you off, your opponent is running a circus and scoffing on your defensive attempts.

Repeating moves is a psychological ploy. As the defender, you think along the lines of, “He has nothing better than a draw!” or maybe even “this position is such a dead draw, I defended so well!”

Then, when he pulls out of the repetition, your thought bubble bursts. “No draw? Hang on a sec, I’m worse here! I’ll have to defend more. Ugh.”.

More experienced players generally react better to this, but less experienced players can break under the pressure.

“If only it hadn’t been for my mistake…,” is something chess players say a little too often after their losses. Your opponents are (hopefully) human, and they make mistakes and so do you. That’s part of the game.

As for dancing around, first of all, what looks like dancing around to someone skimming through the game may not have actually been dancing at all. You try to break through, but your opponent thwarts your plan. Okay, no problem. Just go back and try something else. Your opponent may crack dealing with all the threats. Or your opponent might think he’s out of the woods and gets hit with a little surprise…

In some situations, improving your position before releasing the tension is a good idea, even in positions where there isn’t much tension. By that I mean improvements like gaining space, cramping your opponent’s pawns, securing good squares for your pieces, etc.

Even if those factors do not seem too relevant at the moment, they could be useful in the future. Also, they provide opportunities for your opponent to make a mistake. It sounds degrading, but it works. Instead of having to play forced moves, your opponent now has a dilemma. How to react? What’s my plan? Their reactions can sometimes be wrong. They can chose completely wrong plans. They can get intimidated by what you’re doing and bail out.

An example from my own experience. I had black against a 2000, and we reached this position.


Black to play. How to make the most out of the position?

White’s only real weakness is the d4 pawn. Black has a lot of pressure against it, but white has it well defended. The most forcing move 28… e5 leads to equality after 29.dxe5 Rxd2 30.Rxd2 Rxd2 31.Nxd2 Bxe5.

Then how to proceed? If you found the idea of trying to harass the white knight, you were on the right track. However, if black plays 28…g5, white will respond with 29.g4 and white’s knight is not budging.

Therefore, I played 28… h5! to prevent white from going g4 himself. Kudos if you found this move. 29.h3 is white’s best response, after which I was planning 29…h4 followed by g5, some preparation, and a g4 breakthrough. It may not be much, but at least it is something.

My opponent responded with 29.h4? which seems fine on the surface, but there’s a problem. Can you find it?

Here’s how the game ended.

However, striking at the critical moment is the tricky part of grinding. No more building up your position, dancing around… it’s now or never! First of all, realizing it is a critical moment is hard. Treating every position like a critical moment would probably lead to perfectionism (paralysis) and likely time trouble. Then when you get to the actual critical moment, you won’t treat it like anything special.

Honestly, knowing when it is a critical moment and correctly exploiting it is not an easy subject. It’s mostly an intuitive thing. That’s where experience and skill help. If your opponent is doing something suspicious, try to punish it. If a forced line looks good for you, calculate deeper.

Before agreeing to a draw, try everything reasonable you can. Your opponent might break under the pressure. There have been so many times when I was on the verge of giving up but managed to win after my opponent made a critical mistake. There is no harm in trying. Worst case it’s a draw.

In this game, I was trying to press this position.


I was not happy with my position. My c-pawn will most likely run through, but not before the pawns on the kingside will get traded. Also, the time situation was not in my favor; I had very little time, while my opponent still had a lot.

I played 62.g4+ hxg4 (62… Kf6 63.gxh5 gxh5 64.h4 was another possibility for black) 63.hxg4+ Kf6 64.c5


And my opponent shocked me by blundering 64… Nxc5?? His hope was probably to win my g-pawn, which is not the case. White is winning after either recapture. 64…Rg3 would have drawn. Here’s some more detailed analysis and how the game ended.

The second game is far more complex. First, a little tactic from earlier in the game:


Black to play.

Good job if you found 22… Nxe5! 23.Re3 Qd7!. After 24.Qxd7 Nxd7 the position is roughly equal.

Eventually, we reached this position.


Evaluate the consequences of 40… Kc4 which I played in the game. Calculate as deep as you can.

Here’s the game.

Let’s finish off with a fun one. This game was just crazy. I got a near-winning position out of the opening, was even more winning, blew it, was still much better, and then got back to winning. Soon after the time control, we reached this position.


My opponent surprised me with 42.Rxe6!? fxe6 43.Rxe6. How should black respond?

I responded badly and let white get into a fortress. Here’s what happened.

After some dancing around, we reached the critical position.


How should white react to black’s last move 59…h5?

Here’s what happened in the game.

Slow but steady is the synonym of grinding. Play crafty, try, try, and then try some more. Good luck!


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