Wow -- terrific post!!! Thanks for sharing it here :)
How to Learn Chess

Play, Study, Analyze your games. Play, Study, Analyze your games. Play, Study, Analyze your games.
I think your book list is good, but way too long. It will take someone 5 years to get through all those books. I would cut the book and DVD list down to 15 titles - and when you thoroughly understand and can put into practice what you have learned, you'll be a better player, but you need to keep playing while you're learning.
I responded to an old thread, but I figured this post would help others so I'm posting it here.
Ok, I know this thread is really old, but I read about your problem and just had to reply. So, I hope you get this.
Improvement in chess is a constant problem, because it is true, that for most people, improvement happens in leaps, and not gradually. But there are two fundamental problems within the chess community. 1. ALMOST NO ONE knows how to actually teach chess. The reason is because they simply don't know how to teach. There are a few writers and coaches who know how to teach but they are few and far between. Some who can teach include, Jeremy Silman, Cyrus Lakdawala, Andy Soltis, John Nunn...etc. But for the most part no one knows how to teach chess and that is evident because no one knows where to start.
The only consensus is to start with tactics. Spend about a month to three months on them. For this I recommend the website Chesstactics.org. He has an EXCELENT way of teaching tactics and shows you how to find them even a couple of moves away. And this will help you with your calculation. If the website doesn't work for you, he has two books which have everything on the website called Predator at the Chessboard vol. 1 and 2. An example, is when looking for knight forks do a color scan. When a knight moves it ALWAYS jumps to a different color square. When a knight fork is 1 move away, the knight and the two pieces it is attacking will all be on the same color. When the knight moves it will jump to a different color but it will be able to attack both pieces. He explains this better on his site and books because you have diagrams to see what he means. There are many benefits to starting with tactics. 1. You learn how to do tactics. 2. By learning how to spot tactics, you learn how to avoid your opponent's tactics during the game. 3. And probably the most important lesson is they teach you precise calculation.
Now the problem is where to start AFTER you learn tactics and on this there is NO consensus. Some people like to start with endgames. There are many reasons for this, 1. It can teach you basic mates. 2. There are less pieces on the board so it's easier to understand. 3. It teaches you to coordinate your pieces. But there are three major problems with this. 1. A beginner will NEVER reach the endgame. They aren't good enough yet and as a result will probably get mated long before then. 2. Many of the strategies for the endgame are reversed in the middlegame. Examples, centralizing your king/castling your king, rooks behind pawns/rooks in front of pawns etc. So most of what a person learns in the endgame they cannot use UNLESS they get to an endgame. Finally, even if a beginner gets to the endgame, it's going to be a bad endgame because they don't know how to steer play to a favorable endgame during the opening or middlegame.
After studying chess seriously I believe a person should learn opening principles, then opening STRATEGY first. NOT OPENINGS. The reasons are, opening theory is vast, and it can take a long time to memorize it all. 2. The consensus on Openings is that studying them should be held off for a long time. You REALLY don't need to study openings on any serious level until you reach about 2000 elo. 3. Many people worry about memorizing their openings instead of understanding their openings. This is a problem because once you leave the variations you want to play, you are lost and don't know what to do. The consensus here is: memorization is OK, understanding is better, and understanding PLUS memorization is best. As such you need to understand the foundations of opening strategy in order to understand the openings you play, and what they are really trying to accomplish over the board. For this I recommend Mastering Opening Strategy by Johan Hellsten.
This will help you fair a little better in the opening whether you know actual openings such as the Queens Gambit or Sicilian, or you just play chess and follow opening principles. It will also teach you the circumstances under which you should break those principles, and how you should punish those that do break them.
Then you should learn the principles of the middlegame. The absolute best book I have EVER read on this subject is Simple Chess by Michael Stean. This books is even better than Amateur's Mind and Reassess Your Chess, because this gives you a solid plan on how to approach the game from the opening to the endgame and it also shows you how to use your pieces and pawns together as an interdependent whole. Plus it illustrates the three major aspects of Middlegame Strategy: Pawn Structure, Pieces, and how they work together. To supplement this book I recommend Rethinking the Chess Pieces, and Pawn Structure Chess by Andy Soltis. Rethinking the Chess Pieces, teaches you about how the pieces actually function together, and how to spot and use Imbalances between the pieces to your advantage. For example, the value chart says that a Queen vs. 2 Rooks is roughly equal. But any one who has played with only a queen on the board, with their opponent having two rooks will tell you it's not, for one reason. 2 pieces are better than one. A queen cannot be in two places at once. Pawn structure chess will teach you the most common pawn structures and how to use them to your advantage.
One of the things I have found over my year of study is Masters know how to change a pawn structure to their advantage, and as Michael Stean says in Simple Chess, “The Middlegame is a problem of structure, and the most important feature of that structure is piece activity. You must use your pawns to free and support your pieces.” These three books together will show you how to do that. And to prove it, in Rethinking the Chess Pieces, Soltis says the three most important features of the pieces in a position are: Mobility, Coordination, and Targets. Mobility, Coordination, and Targets are the three features of piece activity. Piece activity is the most important feature of the position, and pawns must free (grant piece activity) and support your pieces, while preventing your opponent from doing the same thing. I can truly say, that the whole game of chess revolves around those three things. See how they are related? Pawn Structure Chess will teach you how to best change that structure and use that structure to your advantage. This is important because piece activity is determined by pawn structure, and pawn structure is determined by the opening.
Also, Soltis is the absolute best at showing how chess players actually think, and debunking a lot of myths about that thinking. So much so, that his books The Inner Game, and How to Choose a Chess Move, actually disproves the necessity of How to Think Like a Grandmaster. Kotov's method is really only useful in certain situations. These two books will show you what those situations are, and teach you how to really think during a game. This cannot be overestimated. Chess is a THINKING game. I can guarantee that the biggest reason you are not improving is because you are overlooking something at the board. There is something you are not seeing, and chances are it's because you are not considering enough candidate moves. That is what these two books are about.
Read the books in this order:
The Inner Game
How to Choose a Chess Move
Mastering Opening Strategy
Rethinking the Chess Pieces
Simple Chess
Pawn Structure Chess
Now, the second major problem with learning chess is that the people who study chess, don't know how to learn. This is a problem with most people when learning anything. The reason is because learning is a skill, it is not something you automatically know. As a result people waste a lot of time trying to learn something, and then they fail because they get frustrated and don't know why they couldn't learn it. There is a specific philosophy to learning and here it is.
Philosophy of learning.
1. The best way to find a solution is to accurately define the problem.
2. The brain cannot learn anything it does not already know.
3. Everyone Learns differently, based upon seeing, hearing, or doing, and you must identify how you learn.
4. Repetition is the royal road to learning.
5. Once you are emotional about a subject, you know it/if you can teach a subject you know it.
Now, what does all this mean. When I started taking chess seriously, I had no idea what I was doing. And honestly no one else did either for the reasons I have already mentioned. I wasted three months before I had any idea how to approach learning the game I love so much. Then I remembered some things my sensei in Karate had been telling me over the years and I started using them for chess and, honestly it has worked beyond my wildest dreams. The reason for this is because I am a trained Philosopher, and as a philosopher I know that all of our actions are determined by how we think, and look at the world. So by remembering my Sensei's teachings I realized I had a philosophy of learning and so I used it.
First I defined the problem, which I hope this post is doing for you. Then I devised a plan based on the definition of the problem, but I organized the plan according the 4 other principles.
The Brain cannot learn anything it doesn't already know. What this means is, the structure of the brain must have something to build from in order to learn it. This takes the form of synapses. If you are going to learn anything the brain must have a synapse to build from. This is why a person who doesn't know how to add or subtract, cannot learn how to do Algebra. They don't have the basic foundation to build from. So this is what I did. As I bought books, I organized and read them from easy to hard, in such a way as they built from one another. This is what I did for you with the six books I recommended already. They are put in an order that will reinforce what you read previously as you move through the list, and as such will help you understand what you will read.
I noticed you have the Art of the Attack. So do I, but what you have to understand is, the Art of the Attack is one of those books you will read for the rest of your life. And when you reread it six months to a year from now, you will pull more from it than you did the first time you read it. It is a VERY advanced book, and honestly it is not the book you should start out with learning how to attack. You should start out with Simple Attacking Plans by Fred Wilson. This is a small book that has they very basic foundational principles of attack. Chances are you won't become an attacking genius from reading this book, but it serves as a foundation for attacking play. Now I'm reading Attacking the King by Yakov Neishtadt. This book is filling in the gaps of Simple Attacking Plans. But because I have read Simple Attacking Plans and am applying what it said to Attacking the King, I am learning a lot more about attacking, which I really suck at. THEN after I've read this book, I will read The Art of the Attack. But not before I read these two books, and know a lot more about tactics. This way I have a foundation to build from, and therefore a way to understand and approach Art of the Attack.
So, what I did is I took the absurd number of books I bought on chess, around 60, and organized them in order from easy to hard, in such a way that I can build on the information I learned from earlier books, and apply them to later books. I will put this list at the end of this post.
Another one of the consensus ideas among titled players is to study grand master games. Now it's not that this advice is wrong, but it is HORRIBLY incomplete. You shouldn't start out studying master games right way. The reason is because you have NOTHING to base what you are looking at on. Yes they make the best moves, but you as the reader don't know WHY they are making those moves. So first you must learn the strategies they are using and how they are analyzing the board BEFORE you study grandmaster games. This is why I have 6 phases to my chess study.
Phases of Study
1. Basic Strategy and Tactics
2. Technique of Restriction
3. Defense and Dynamics
4. Openings and Endgame
5. Soviet Chess Strategy
6. Grand Master Games
Look at all the steps I am going through BEFORE I study grandmaster games. (Note, I have two complete steps before I start learning openings.) This is because I know the Brain cannot learn anything it doesn't already know.
Everyone Learns Differently. No two people learn exactly the same way. But there are three areas of classification you can use as a general guideline. People learn with some combination of Seeing, Hearing, and Doing. What this means is some people are better at learning if they can physically see what they are doing. This is where charts, and videos comes into play. Others, learn by hearing, they can learn from listening to a lecture, or reading a book. Then there is doing, which means a person learns by the physical action of doing something. In this case, PLAYING chess. If you learn by doing the best thing for you to do, is to play.
When a person recommends how to learn chess on Chess.com their comments will fit into one of these three categories, and they are using what works best for them. You need to find what works best for YOU. I personally learn by hearing, so I am able to learn from a book very well. Others are not able too. But they still need the information, so they can't avoid the book, but, maybe they learn better from videos to get information. Or maybe they read a little bit and learn best when they apply it to their own games. Chess.com is really good for both of these areas.
Repetition is the royal road to learning. This is probably the most important principle, other than the brain cannot learn anything it doesn't already know. The reason is because you must be consistent in your practice and study of chess if you want to get better. For example, I learn from hearing, so I read a lot of chess books. But it doesn't stop there. I am taking notes as a read. Then I go through the notes and reduce them to their bare essentials, getting to the core idea they are trying to tell me. Then pull out all the information, as it relates to certain subjects. I put all the information about the pieces in one place, information about pawns in another place, attacking in another place, the center...etc. Then I take those notes and I see how they relate to other notes I have taken. I see how my notes from Mastering Opening Strategy, relates to Simple Chess, which relates to Rethinking the Chess Pieces. Then I take that information and apply it to all of my games, whether online or over the board. This way I am constantly working with the information I am reading until I am emotional about it, and can teach it, then I know it.
Now the other reason I do this is because I am a relational thinker. I am very good at taking individual things and ideas and seeing how they relate to one another. This is why taking the notes and seeing how they relate to each other is so important for me. But this is how I'm learning, it may or may not work for you. But this is the problem about chess. EVERYTHING in chess relates to EVERYTHING else. It is relational thinking. This is why those who play chess, regardless of skill level, improve in their other studies because it teaches them to think in relational ways. And this happens whether you realize it or not.
I hope this helps. I know it's long, but that is the nature of chess. There is SO much you need to know in order to get better. Honestly right now I”m at about 1500. But, I have gone from 1100 to 1500 in a year, and they say it should take about a year to go up 100 points. And I have done this basically without help. I don't have a trainer. I have a few friends I play with at my chess club. But I have basically learned on my own. So I think going up 300 in a year is pretty good. And I am still learning and I am still getting better. The key is to keep going even when I get a little discouraged, but at the moment I get discouraged it seems something happens and I get better.
I will end with this. I am not very good at attacking, so I am reading Attacking the King. One of the principles when attacking is to trade off the defenders. Even though I have read this in multiple places I never really understood it, until, while reading Attacking the King, I noticed all the space around the king as defenders were being traded off. This allowed the remaining pieces to attack the EXPOSED king. I never noticed that before, and noticing it changed my understanding of this principle, and therefore how I thought about it. This is one example of how the learning process functions during your study. And it is one example of why people don't improve, because even though they are reading things their understanding of it, isn't evolving.
I hope this helps.
Chess Study Plan
Phase I: Basic Strategy and Tactics
Simple Chess
Simple Attacking Plans
Rethinking the Chess Pieces
How to Choose a Chess Move
The Tao of Chess
The Amateur’s Mind
How to Reassess Your Chess 4th ed.
Mastering Opening Strategy
Pawn Structure Chess
Understanding Pawn Play
Dynamic Pawn Play
Pawn Power in Chess
Chess: 5334 Problems, Combinations, and Games
Predators at the Chess Board I
Predators at the Chess Board II
Attacking the King
Art of the Attack
Sacrifice and Initiative
Mastering Endgame Strategy
Catalog of Chess Mistakes
Phase II: Restriction
My System
GM Milik Kachiam Videos
Karpov's 7 Bases of Restriction
Karpov's Strategic Wins I
Karpov's Strategic Wins II
Life and Games of Tigran Petrosian
Phase III: Defense and Dynamics
Art of Defense in Chess
Petrosian's Legacy
How to Defend in Chess
Secrets of Defense in Chess
How to Play Dynamic Chess
Dynamic Chess Strategy
Phase IV: Openings and Endgame
Mastering the Chess Openings: Vol 2*
Play the London System
Playing 1d4: the Queen's Gambit*
Play the Queen's Gambit *
The Slav Move by Move
The Caro-Kann Move by Move
The Colle Move by Move
The Torre Move by Move
Starting Out: The Scandanavian
The Modern Scandinavian
Silman's Complete Endgame Course
Dvoretsky's Endgame Manual
Secrets of Pawn Endings*
Phase V: Soviet School and Modern Strategy
My System
A Contemporary Approach to the Middlegame
Soviet Chess Strategy
Soviet Middlegame Technique
Questions of Modern Chess Theory
The Ragozin Complex
Lessons with a Grandmaster I
Lessons with a Grandmaster II
Positional Chess Sacrifices
Sacking the Citadel*
Secrets of Modern Chess Strategy
Road to Chess Improvement
Phase VI: Grandmaster Games
Studying Chess Made Easy
What it Takes to Become a Chess Master
Life and Games of Tigran Petrosian
The Games of Tigran Petrosian I
The Games of Tigran Petorsain II
Karpov's Strategic Wins I
Karpov's Strategic Wins II
Gelfend: My Most Memorable Games
Complete Games of Bobby Fischer
Capablanca Move by Move