How to think About Chess

I'm a keen, but not very accomplished, chess player. I'm looking to understand the basics of good chess strategy.
I started playing chess when I was 6, and played seriously until the age of 18. My career highlights include 30th in the European U18s, captaining/vice-captaining England at most age groups, playing for Oxford in 3 Varsity matches and achieving rankings of 195 ECF and 2200 FIDE. I'm a software engineer at Stripe and blog at robertheaton.com.
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13:27, 06 May 20 (edit: 13:28, 13 May 20)
This Taaalk was written on the first version of Taaalk in 2016.
The archive.org version is available here.
Joshua Summers
18:08, 07 May 20
A lot of people write about chess as having an opening game, a middle game and an endgame. When you're playing is that what's going through your head?
Robert Heaton
18:08, 07 May 20
Everyone has an opening repertoire. Many people just have one answer for each question they might reasonably expect their opponents to ask, which means they get very good at playing those answers, but equally become very predictable. There are some openings that are razor sharp and precise, and require knowing many 15-20 move variations in order to not get destroyed without the game even starting. I personally prefer openings that are more conceptual, which tend to be slightly more flexible, require much less knowledge, but arguably lead to somewhat more boring positions because of this.
So when the middlegame comes around, it's probably the kind of position I've played many times before. My strategy is usually to throw lots of pieces at their king and hope they die or I can win some material. Since I'm hoping to win at this point, I probably don't start thinking explicitly about the endgame until little suggestions of things that might become relevant start cropping up. So if pawns become isolated or doubled, or we end up with opposite colored bishops, or with a bishop on the same color square as most of our pawns, etc. If I can take one of these small positional advantages then I will, and then effectively "bank" it until the endgame actually comes around. Having one or more of these might make me more likely to head towards an endgame too.
Endgames are really hard and require a lot of technique that I don't really have. Fortunately most other people don't either, because you just don't get to play that many of them.
It probably is fair to say that I'm pretty aware of the opening/middlegame/endgame distinction. The opening is where I'm playing pretty much from memory, the middlegame is where I try and win, and the endgame is what I might head towards if I think I have a tangible advantage but try and avoid otherwise.
Joshua Summers
18:08, 07 May 20
So when you say that the endgame is what you might head towards - is the endgame not just the 'end of the game'? In which case won't most games have one? I know in the extremely amateur world of chess that I play in that most games come to a end where one side is actively checkmated. Is the endgame more unusual the higher up you go because a party will often resign when one side is in a dominant position?
Robert Heaton
18:10, 07 May 20
I guess this is a question for statistics to answer properly, but my gut says that there possibly are fewer endgames in higher level play. If you lose a bishop or a knight without any obvious compensation, you will almost definitely resign on the spot. That said, it's probably also true that fewer boneheaded mistakes mean that neither side may have had much of a chance to win before the endgame. Overall I'm not sure!
But when I say "might head towards the endgame", I mean that I might deliberately choose to swap off pieces and accelerate progress towards the end of the game. If I'm a pawn up then trading off pieces is likely a huge win for me, because whilst a queen + 2 rooks + 1 bishop + 2 knights + 7 pawns v the same but 6 pawns is not a huge advantage, a bishop + 5 pawns v a bishop + 4 pawns probably is. Small material advantages are a much bigger deal in the endgame and leave less room for your opponent to generate compensation, so if you are slightly ahead then deliberately swapping off pieces is very important. Games can naturally meander towards an endgame where neither side is too psyched about their chances, or they can be forced.
Joshua Summers
18:10, 07 May 20
OK - that makes a lot of sense. You mentioned that you like to keep your openings of a 'conceptual' nature. What kind of concepts are you basing your openings on?
Robert Heaton
18:10, 07 May 20
Honestly I like openings that allow you to put your pieces on nice squares without thinking too hard, and then throw them all at your opponent's king. This is not a very sophisticated strategy, but it can be very hard to deal with if you aren't prepared (this is a good example). If you can get off the beaten track without doing anything too insane then you become much more familiar with the kinds of positions that result than your opponents, and develop a big box of patterns that have worked in the past.
This becomes somewhat less effective the higher level and more famous you get, as you start to become notorious for particular openings, and opponents can start preparing counters to them. This is where a degree of flexibility and unpredictability becomes invaluable, so that your opponents can't just put all their time into preparing for your Stonewall Dutch or Trompowsky, and also have to keep in mind that you might throw in a Benko Gambit or English Opening. It can be worthwhile playing these alternatives in high profile tournaments that will get their games into databases that your future opponents will see and get confused and upset by.
Joshua Summers
18:11, 07 May 20
The part on variation makes a lot of sense. So what are nice squares and what makes them nice?
Robert Heaton
18:11, 07 May 20
"Nice" squares is obviously a super-vague concept, but in this situation I mostly just mean:
Knights in the middle of the board
Bishops pointing towards the king
Rooks on open files or behind pawns that are marching towards their king
Joshua Summers
18:11, 07 May 20
OK - now we're warming up!! A few things to deal with:
1) Why is it good to have knights in the middle of the board?
2) Why is it good to have bishops pointing at the king?
3) And i) what is an open file? and ii) why do I want my rook on it?
Robert Heaton
18:12, 07 May 20
1) Knights on the edge of the board don't attack many squares, knights in the centre of the board do. Because of their uniquely short range, they are the one piece that really benefits from being in the centre. A rook or bishop in the corner can still rake across the entire board, but a knight in the same spot looks pretty dumb.
2) If you want to attack the king (I do), you need to have your pieces attacking him and the squares around him! Even if you aren't planning on immediately checkmating anytime soon, you may be able to use threats against him to force smaller concessions or weaknesses.
3) An open file is one that isn't blocked by any of your pawns or pieces, and so if you put a rook at one end of it you'll be probing into some part of their position (hopefully a weak part!). This is the most direct way for your rooks to influence the game. As mentioned above, you don't necessarily need to be destroying or capturing anything in order for your pieces to be making your opponents' life awkward, so principles like "rooks on open files" will almost always be good things to at least look out for.
Joshua Summers
18:14, 07 May 20
Right. Would you say you're setting yourself up in the strongest position possible to deal with the largest number of variations down your opponents end (defensive) or setting yourself up to maximise your attacking options? Or a balance of the two?
When I'm playing with friends sometimes it feels like there is an unspoken agreement to let the other player 'set up' so to speak. To get their pieces into the strongest structural position before the WAR takes place. When you're playing is this something that happens? Or are you looking to start WAR while you set up your structure?
Robert Heaton
18:15, 07 May 20
The more experienced the players, the bigger the difference between playing white and black. At the very very highest levels winning with black is really quite an impressive achievement, and black will often go into a game playing for a draw. The advantage of the first move is very pronounced, and sets the tone for the entire game, with white generally calling the shots. Attempts by black to generate active counterplay are often very risky. At lower levels, black can afford to be a bit more ambitious without worrying too much about opening up tiny weaknesses that get ruthlessly exploited.
The more you actively engage with your opponent's pieces and position early on, the less (generally speaking) time you are spending on getting your pieces out and putting them exactly where you want them. This potentially creates weaknesses of your own. So the sharper and more confrontational the variations you want to play, the more opening theory you need to know to make sure you don't do anything that is already known to be a mistake. I don't like opening theory (because I'm a lazy player), so I tend to err on the side of just trying to do my own thing whilst making small prods at my opponent here and there. This is definitely a deficiency in my game though, and means that I'm rarely asking particularly difficult questions of my opponents in the opening.
Joshua Summers
18:16, 07 May 20
So the aim when black is to survive and make sure you're doing enough sensible things to not get exploited because of the disadvantage of moving second.
And the aim when white is to go out there and win. When you are white, what are you looking for to begin the post opening attack? And would you ever begin your attack during the opening phase if you noticed a mistake in your opponent's opening play?
Robert Heaton
18:17, 07 May 20
I think we're starting to get beyond the realms of where we can usefully talk in generalities, and into the realms of where the answer is always "it depends".
It would generally require a fairly gross error for someone to expose their king in any meaningful way in the first few moves, but you often want to be "attacking" anyway by asking your opponent questions that they have to answer, preventing them from just doing what they want. So you might be developing your pieces and attacking their pawns, or seizing the centre and cramping them for space, or tying their pieces down to defending each other. None of these efforts are likely to immediately cause checkmate, but they are still "attacking" in the sense that they force defensive responses from your opponent. It's rare that you will sound the charge with a specific move, but more often you'll gradually build up the pressure, without giving your opponent a chance to respond
Joshua Summers
18:17, 07 May 20
Yes, sorry. I didn't mean when you begin the final attack on the king, but more when you turn on some sort of aggressive pressure.
When I'm going through the opening motions the majority of them are not particularly aggressive or even confrontational (as long as my opponent is doing the same). They are very focused on my own structure and normally all take place within my half of the board. So when I'm playing there's normally a move where the pressure goes 'on'. That's normally when I force a direct defensive response from my opponent (i.e. do something or your piece will die!). I'll do this early if I notice a mistake in their play and at some random point if nothing obvious emerges.
It sounds like when you're opening the pressure is always on. In your opening phase what is the balance like of moves that are more internally focused (although they might be gaining you space in the middle of the board / be generally 'aggressive') and moves that force a direct defensive response?
Robert Heaton
18:19, 07 May 20
It 100% depends on the opening variation. In the sharp but almost definitely technically unsound Muzio Gambit, white sacrifices a knight on move 5 and is attacking until they either win or run out of pieces from then on. Whereas in a Stonewall Dutch, black is almost definitely just going to play most of f5/e6/Nf6/d5/Bd6/0-0/c6/Nbd7/Ne4/Ndf6/Bd7/Be8/Bh5 and then look up and see what white has been up to.
A move that asks your opponent questions obviously doesn't have to be overtly aggressive as such. At higher levels of play, getting a knight to a good square or forcing someone to trade off a "good" bishop can be non-trivial wins, so moving your knight to a square where it might next turn be able to hop into a hole in the centre can constitute a "question", or moving a pawn so that next go you might be able to kick their bishop and force it to trade with your bishop. When there are more possible small wins, there are more possible ways to threaten these small wins. When you're just starting out, as long as your opponent isn't directly threatening to take one of your pieces for free or checkmate you, you probably don't have to worry too much about them gaining a microscopic positional advantage.
Joshua Summers
06:46, 12 May 20
So, after you've got your setup in a roughly sensible position, what are you looking for to 'begin the attack'? From what I understand the most common way to do that is to push own of your pawns up the board to add pressure to their position - a 'pawn break' I believe. 
Knowing when to do this has always left me lost. I feel I am never certain that it is a sensible thing to do. I can calculate for a bit, but my calculations end in an unclear and fairly muddle, with no player significantly ahead of the other.
Is a pawn break how you normally start your attack? And what clues are you waiting for to begin?
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