Ev asks: Is cursing allowed in the mailbag? If so, then I FUCKING HATE RAPID. Every game is the same story: I get an interesting position and blow it under time pressure, knowing all the while that I could have put up a decent fight if I'd only had a few more minutes to think. For that reason, I've completely eliminated rapid from my chess diet. Am I wrong to do so? Is there a use for rapid chess (as there is for blitz) if one's goal is to improve at chess in longer time formats?

Every time control has its own tempo. It can definitely take awhile to get the feel for rapid (or blitz, or classical) if you’re not in the habit of playing it. You’re not alone in hating rapid. Coach Dan Heisman is on the record saying that rapid is the worst format for improvement.

https://youtu.be/_-UKPDB-s98

A word of clarification, since the title of that video could be misinterpreted: Dan isn’t saying rapid makes you worse at chess, he’s just saying it’s less efficient at making you better than blitz or classical.
I take a different tack. I find rapid to be a great tool for improvement (for myself, at least). I find each time control emphasizes different parts of the game.

Blitz — Openings and simple tactics
Rapid — Structure-specific knowledge and typical plans
Classical — Thought process and going beyond assumptions

To expand a little on where I think rapid is uniquely valuable... Advanced strategic knowledge is largely structure-dependent. “In situation X, you do Y.” For me rapid is the best way to build up this kind of knowledge. Because blitz is so fast, the game is often decided by “random” tactics that may not be particularly thematic for the structure. In contrast, classical rewards beyond the typical, finding unique or unexpected ideas. In my experience it’s rapid where understanding these typical ideas is most powerful, and it’s a good balance of slow enough to have a real game, but fast enough to get a lot of games in (and see a lot of patterns).

Since each time control emphasizes something different, you could argue that the optimal approach is a mix of all the different time controls. But it’s probably more accurate to say that there is no optimal approach, and many things can work. My fundamental theorem of chess improvement:

Improvement = Time * Focus

Whether that time is divided up into a few classical games, many blitz games, or a medium number of rapid games, probably does not matter too much as the end of the day — if you can maintain focus!
All in all, rapid certainly can be a useful format for improvement, and it’s one of my personal favorites, but if it’s not your cup of tea, you don’t have to force yourself to play it. Everything you could learn from rapid games, you could learn in other ways as well.

Dan asks: Everyone knows you shouldn't memorize an opening move you don't understand. But how can you gain an understanding of any given move? For example, if there's a position in your opening where you don't know what to do, and you look in the masters database to find the most common move, and you don't understand why they're all making that move, what should you do?

I agree 100% that you shouldn’t memorize moves you don’t understand. Many players do this, but really, if you don’t have any explanation for why a move is the best one in the position, why on earth would it help you win more games?

As far as how to gain a better understanding of a move, there are several options...

1. Have a coach or friend explain it. If you know someone who’s a real expert in the opening — they’ve been playing it for years, keeping up with the theory, have practical experience, etc. — they will be able to explain how a move makes sense within the context of the opening. If you have access to such a person, this is probably your most efficient option, but of course most of the time you probably won’t.
2. Books or courses. There is a wide range of quality in opening books/courses. The best ones have very good explanations of why certain moves are important. So, if you have a good book/course, it may have an explanation of the move you’re wondering about.
3. Engine. Now we are getting into figuring it out for yourself, which is probably what you’re really interested in. You can do this with the help of the engine, but it requires a bit more than just looking at the main line.
   1. Compare alternatives. Look at plausible alternatives to the top move, and follow the engine’s top line in those cases. Often the contrast between different lines is very telling. For example, the top move may answer a threat that was not immediately obvious.
   2. Play against the engine from the opposite side. That is, if you’re preparing the opening for Black, play as White for a few moves. Play your intuitive first move, wait a few seconds, and hit space bar to have the engine play its top move. Repeat this for a few moves. Typically your position will deteriorate quickly. The point isn’t to try to beat the engine so don’t break your brain on this one, just play plausible moves quickly. You’re trying to get a sense for how human moves might be refuted.

Finally, keep in mind that the most common move in the masters database might not be the best move, or it might be one of many decent moves. Many players overestimate the value of the “book” move compared to alternatives. In most opening positions, there are multiple viable moves.

By the way, I’m running an online workshop on preparing your own opening files coming up soon.

John asks: In your book, Evaluate Like a Grandmaster, there are some interesting positions where the evaluation of the position heavily favors one side because the other has no counterplay, or the best move is somewhat counter-intuitive but is strong in part because it leaves the opponent with no counterplay. Do you have any tips on how to recognize when one side lacks counterplay? The absence of useful pawn breaks seems like one example, but I'm curious if you can think of others.

Your example of no pawn breaks is a great point. More broadly, it’s a situation where there’s just not much the opponent can try to do. A good way of getting at this is to think about if they had two or three moves in a row. Could they do anything? Don’t take this completely literally – still assume you would move a piece that was attacked directly, for example. But if they had a few moves in a row to build up their position, could they get anything going? This is what I’m thinking of when I talk about one side having no counterplay: there’s not much they can do, even if they had the time.

I’ve always thought prophylaxis or preventing the opponent’s play is a more advanced concept for that reason. To advance your own strategy, you just have to figure out one good thing to do and do it. To stop your opponent’s play, you have to figure out all the things they could do and stop them. In this sense it takes the skills involved in proactive strategic play and adds a couple of layers.

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