My Mistakes


  • Being afraid to lose
  • Playing “hope chess”
  • Spending incredible amounts of time “studying” but not mentally exerting myself
  • Fixating on openings and trying to stupidly memorize chess
  • Relying too heavily on computer analysis
  • Not paying attention to the meta-learning process

I learned chess at around age 11 or 12 and soon after joined Polgar Chess Club which was in Queens, NY at the time. I was immediately one of the best kids there and regularly won almost all the scholastic tournaments.  I became afraid to lose and whenever the position got tough, even against players I’d be expected to lose against, I would often start shaking. I would wish that someone would have taught me to learn to invest in loss, a concept typically learned from the domain of martial arts, but of course applicable to any art and any learning. I remember sometimes seeing Fabiano Caruana come to the club and play when he was only about 6 years old. I didn’t know back then that today he would be one of the top 5 highest rated players in the world. It is not surprising to me now, as I recall that I never saw him cry or shiver at the chessboard when he was losing. Somehow at a very young age he had the right mindset.

Throughout my chess development, I also would often play “hope chess.” In the linked article, Dan Heisman breaks down what I call “hope chess” into more specific subcategories (one of which he calls “hope chess” so hopefully it is not confusing), but I am referring to it in a more general manner. Sometimes I would sit and concentrate at the board for a long time, but it is hard to call what I was doing “thinking”—rather it was just worrying and hoping. That is either hoping that my opponent would make a mistake and fall for a trap, or hoping that the move I played would be good despite that I didn’t think hard for my opponent.

As a kid I also recall that I had (in my opinion) the work ethic of a champion. I had incredible discipline and would spend hours going through chess positions in my books. Despite this effort, I never achieved the type of success I thought I should have. I was at some point in the top 100 list for my age (though nowhere near the top of that list), but soon after hitting my first real slump, I lost interest in chess entirely (due to depression) and stopped playing for some years.

Some time later, I had a resurgence in my efforts and started to put in what felt like a “last ditch effort.” I began to “study” chess again, not realizing that I was going to repeat my past mistakes. I recalled that once, my childhood friend, Lev Milman, who is now an International Master, made significant improvements studying on his own. When I had asked him what his method was, he said that he would “Fritz everything.” Fritz is a computer chess engine of at least Grandmaster strength. I took his advice a bit too literally. I played many blitz games online and “analyzed” all of them with whatever the top engines were at the time. I developed an impressively sized database with all of my so-called analyses, covering a tremendous breadth of opening and middle game positions that I was likely to run into or had run into in my games.

I developed some good techniques of using chess engines to aid in analysis and understand of a position, and even a sophisticated understanding of which engines to use for which positions. Some of those skills are useful. However, in the end, I made no noticeable progress to show for my efforts and I once again dropped chess almost entirely for a few more years. I can see now that I had tried too hard (once again) to use my work ethic to improve, and bypassed the type of real mental effort that is required to do real learning. Chess is a complicated game that can’t be memorized and brute forced. This is obvious from an objective standpoint, but I see many people falling into this same trap of relying on sheer effort and will. It is from Tim Ferris that I learned of the Pareto Principle: for most events, roughly 80% of the effects come from 20% of the causes. Sometimes that is more like 99% to 1%.

I’ve made many mistakes in my learning process. Some of the worst ones are psychological. The biggest mistake is not so much particular to chess, but to learning in general. It’s important when you’re trying to improve at anything, to be critical of the process itself. That is everything from the plan you set out for yourself to the actual mental processes that you are going through in executing that plan. Just as important is to be keenly aware of your emotions. It is sometimes, as it was with me, just when you are making breakthroughs that you feel like giving up, and sometimes when you feel very confident that you make your biggest mistakes.

I’ve outlined here some of the mistakes I’ve made and the utter failures that have led me to quit chess twice now. In future posts I want to outline and dive into their opposites—positive changes that I’ve made which are contributing to my improvement.

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