Long Think. Wrong Think.

In the 2026 FIDE Candidates Tournament, GM Hikaru Nakamura was chasing the tournament leader, GM Javokhir Sindarov. After twelve moves, Sindarov played a move that Nakamura hadn't prepared, and Nakamura fell into a 67-minute-and-44-second think. It's unclear what he was pondering, but he made a mistake and soon fell into a worse position, one that was impossible to defend in time trouble.

Nakamura's experience of a long think followed by a mistake is very common. It's rarely a good idea in chess to spend more than a few minutes on any move. That's because the accuracy of your calculations is typically more important than their depth, and it's hard to tell when you're going to need the time later in the game.

The Sadistic Exam

In his book Move First Think Later, IM Willy Hendricks describes a chess game as a sadistic exam. You can think of a game as a test where any wrong answer could result in a failing grade. In addition to that pressure, there's no way to know in advance how many questions will be on the test. As a result, you can't afford to spend most of your time on one critical moment in the game. There's no telling how many more moves will require your time in the future or which moment will be your most difficult. 

Returning to Nakamura vs. Sindarov, GM Rafael Leitao writes that Nakamura's 20.Kh1 was "the last time that Nakamura could really fight to save the game." You can see Leitao's full notes below: 

It's worth noting that Nakamura had only 16 minutes left on move 20 and trailed by nearly an hour on the clock. He spent 27 seconds on the move that let the game slip from difficult to lost. He must have wished that he had some of that time back to help when he needed it.

Thinking Sideways

Chess is a famously complicated game. White has 20 options on the first move. Black has 20 replies to each of those, and the possibilities soon become nearly limitless. That's why no one can see many moves ahead in most positions. Unless there's an incredibly forcing move, it's far more essential to see a wide breadth of moves, rather than trying to make one in-depth calculation.

IM Jennifer Shahade titled her recent book Thinking Sideways. In it, she discusses how "the clarity that strikes chess masters is not usually a light at the end of a long tunnel, but the best move in the moment." GM Anna Muzychuk concurs, explaining that "it's not the length of the lines manage to analyze, but the precision of the lines." It's essential to avoid simple blunders and much less important to calculate any line deeply. 

One of the longest calculations in my tournament career offers a good example of what happens when we focus on one long calculation. How much would you examine in the position below before deciding on a move?

I calculated a sacrifice seven moves deep, played it, and won the game. Sounds great, right? Well, there are several reasons why the time spent on the sacrifice wasn't all that useful.

1. There was a non-sacrificial option on the first move that was just as strong.
2. I missed a better option, three moves into a seven-move combination, indicating that everything after that was arguably a waste of time.
3. My opponent responded to my sacrifice by immediately playing a move I hadn't even considered. 

This is what normally happens when someone stretches to calculate many moves ahead. Most of the time, that player will miss something early in the variation, rendering the rest of their calculation irrelevant. That's time that would have been better spent elsewhere.

The Wrong Rook Problem

Often, we spend a long time thinking about a move because two options seem very similar and it's hard to determine the difference. A common example of this theme is the famous "wrong rook problem." 

"Some people spend a lot of time on trivial decisions , like the sign-off on an email, then run out of time for much more important tasks. Chess players do this too. We call it the wrong rook problem."

My chess & decision-making interview with @TheEconomist is now on video too! pic.twitter.com/yu9D46Igow

— Jennifer Shahade (@JenShahade) February 20, 2026

Here's an example of a position where someone might spend a long time trying to decide which rook to move to d1. In his My Great Predecessors series, GM Garry Kasparov spends two paragraphs praising GM Boris Spassky's choice of rooks in the position below. 

However, even today, GMs still play the rook move that Kasparov considers inferior. Modern engines agree with Kasparov about what move to play, yet the advantage is minimal. White is a tiny bit better in either case. If you were to spend 10 minutes in a classical game or perhaps even ten seconds in a blitz game, it wouldn't be worth it.

Supposedly, GM Savielly Tartakower, one of the best players in the early days of the 20th century, advised that "Whenever you have to make a rook move, and both rooks are available for said move, you should evaluate which rook to move and, once you have made up your mind, move the other one." He was probably joking, but maybe Tartakower's advice is worthwhile. When two choices look similar, you should trust your judgment and just make one of them. Whether you make the one you think is best hardly matters.

How much time do you spend thinking during your games? Let us know in the comments.