After playing both Chess and Go seriously for a few years now (many years with Chess), I've noticed something about my experience with the games that is distinctly different. What I'm referring to is the nature of improvement. As a Go player, I've found that whenever I begin to make real improvement, it always begins with me losing far more games than usual and my rank significantly declines until I break out of the cocoon and end up being stronger than ever. I believe I've heard a proverb that speaks about this; something along the lines of "lose three stones before gaining one." I imagine that this is common among players which is part of the reason for posting this thread: to read about others experience with improvement. I can compare it to a basketball player who makes X number of shots that he attempts. One day at practice, the coach pulls him aside and helps him work on some adjustments in his technique. Though the player is actually shooting the ball "better" or more correctly than before, the immediate result is that he misses a lot more shots than he's used to. This is because his new and improved technique feels a bit awkward at first and takes getting used to. In Go, I believe that the reason for this phenomenon is due to the fact that improvement begins with a deeper theoretical understanding of the game which means that you're now attempting to pull-off things on the goban that you wouldn't have thought of before. Though your thinking has improved, it takes time before your reading skill catches up, allowing you to properly execute your new technique (though I could be very wrong about this theory).
I just don't see the same thing in my Chess game at all. With Chess it's more simple: you play/study a lot and your skill improves and your ranking goes up. Take some time off and you begin to get sloppy and your level of play is diminished. I'm interested to hear from players of either game about whether this is true for them as well.

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Thinking like a go player during a game of chess is like bringing a knife to a gun-fight. Thinking like a chess player during a game of go feels like getting knifed while you're holding a gun...

I find the one step backward, two steps forward pattern to be true in chess too, though a bit less so. There's more pattern-matching in Go than in chess, so you will learn "play X because it's good shape" but not know well how to follow it up yet. This does happen in chess too when it comes to strategy; you'll learn that certain ideas are good in certain pawn structures, for example, but not be good at executing them yet. There's also a learning period when learning a new opening where you make the moves you're "supposed to play" but don't really know what to do in the resulting positions yet. Still, as you say, the uncomfortableness and awkwardness with new ideas seems more common in Go.

I have absolutely had the experience in chess, as in Go, of taking some time off from the game and finding that I've forgotten some of my bad habits in the meantime.

(For reference, I'm 2000 USCF and 4k AGA)

Same seems to be true about Go for me … I have just one question: could it be that, in this phase, of these “far more games than usual” that you lose, a greater amount is due to resignation than before?

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“The only difference between me and a madman is that I’m not mad.” — Salvador Dali ★ Play a slooooow correspondence game with me on OGS?

A good question which I have no answer for. What are you getting at?

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Thinking like a go player during a game of chess is like bringing a knife to a gun-fight. Thinking like a chess player during a game of go feels like getting knifed while you're holding a gun...

Well, I think it may be that, as we learn and realize how much of our play has been really awful, we tend to resign earlier, namely: as soon as we realize we have blundered badly — where before we’d have fought on … and maybe could have won because the opponent would also use their blundering opportunities

Reminds me of how we sometimes, as our conscience develops, may believe that we’re less of a “good person” than we have believed before …

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“The only difference between me and a madman is that I’m not mad.” — Salvador Dali ★ Play a slooooow correspondence game with me on OGS?

Very cool. I love all the love lessons that spring out of Go. As for resigning more often, I think I probably do but haven't ever made a note of it until you mentioned it. However, it seems to me that the reason for this is, as I said in the op, our understanding surpasses our reading ability to the extent that we play more "ballsy" strategies and when we fail to execute, we end up falling behind much earlier in the game than before. Think of those game where you have you're opponent dead to rights within the first 50 moves meaning that you'll win by a landslide, however, you miss your mark on the final kill stroke and he lives, meaning your position is wrecked (perhaps stronger players would advise against this model of play anyways).

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Thinking like a go player during a game of chess is like bringing a knife to a gun-fight. Thinking like a chess player during a game of go feels like getting knifed while you're holding a gun...

Getting worse before getting better is not unusual for a lot of pursuits. But that was not my experience with go. I think that is because I started out playing against very much stronger players, and when I started studying the game I played over a lot of pro games. As a result, I don't think that I picked up a lot of bad habits that I had to unlearn.

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The Adkins Principle:
At some point, doesn't thinking have to go on?
— Winona Adkins

Visualize whirled peas.

Everything with love. Stay safe.

I've never studied chess as intently as I have applied myself to go, but as a general rule my improvements have come from making fewer blunders rather than correctly applying novel concepts. I would guess this holds for most players below an expert rating, and perhaps beyond. (Though I could be an exception; my ability to solve individual tactics problems generally well exceeded my playing strength. Even if I made the right move nine times out of ten, one mistake in chess can be devastating.)

At low (kyu) levels of go play, a single mistake is not usually game deciding. Because of this, I feel much more freedom to focus on learning and applying grand concepts in my games. However, attempting to apply a new concept without the reading ability to take advantage of the resulting position usually leads to a (temporary) dip in my level of play. When I become more familiar with that position and/or my general reading ability catches up, my level of play is generally higher than it was before I tried out the new concept. (As a concrete example, my initial attempts at responding to a corner approach with a pincer did not go well. However, it's an important strategy at higher levels of play. I needed to fail many times (and am still failing sometimes!) before seeing a positive impact on my game.)

The feeling that a game of chess is about avoiding mistakes more than implementing a large scale strategy is, I think, a big part of what kept it from being my favorite game. Go has always felt like it offers more opportunities for fighting my way back into the game after a mistake.

Thanks for the info
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