My Journey To Chess Mastery

I grew up in the former Soviet Union, where almost everyone played chess to some degree. It was also something that was studied very rigorously from an early age by those who wanted a chance to excel, the same way that math or science was. In St. Petersburg, the best chess school was at the “Dvorets Pionerov” or the “Palace of the Pioneers.” That’s where future Grand Masters trained, typically from an age of 5.

My family is Jewish. In the Soviet Union, that was something that was written in your passport. In the United States my passport’s “nationality” box states “United States of America.” In the Soviet Union that field would say “Jew.” And being Jewish there meant that you were frequently treated as a second-class citizen.

When I was around six, my mother brought me to the Dvorets Pionerov to enroll me in the chess school. They sized us up, and asked for our papers. As soon as they saw that we were Jewish, they told us that they didn’t have a spot for me in the chess school. They did suggest that perhaps I might want to study checkers instead. And that’s how I achieved “vtoroy razryad” or Class B in… checkers.

Having played chess casually in the Soviet Union, I only began to study it seriously when we immigrated and came to New York. The first few years in the United States I was too busy trying to survive – learning a new language, getting used to a new country, trying to make some friends. However, when I started at Stuyvesant High School, my subway trip to school took me past the stone chess tables by City Hall. Some days after school, before ducking into the yellow “R” subway station, I would swing by and mostly watch. It was a scene much like the scene in Searching for Bobby Fischer where the young protagonist is playing against chess hustlers in Washington Square Park. I was hooked.

I didn’t have a master coach. I didn’t have a good technical foundation to build on. So I bought some books, and started reading.

My progress was painful and slow. I didn’t know how to study chess properly. There was a myriad of books to choose from. Books on openings, the middle game, tactics, the end game, and a whole host of other topics. I don’t remember exactly how I chose among them. My guess is that I looked for ones by strong players on each area of the game and hoped for the best.

I started to compete in tournaments, with mixed success. My rating improved, and I got stronger. I started a chess club and revived the chess team at Stuyvesant. I was not the strongest player, but I was able to get us funding, and we ended up winning the nationals my Junior year.

All this time, while my chess kept slowly getting better, it was being built on a shoddy foundation. I felt like I hit a wall, and couldn’t get beyond a certain, quite mediocre, level. Chess is a game where learning it from an early age correctly confers a huge advantage. That’s when our brain plasticity is highest, and getting the right foundation allows a young kid to make dramatic improvement in a few short years. It wouldn’t be at all uncommon to see an 8 or a 9 year-old kid who has studied for only a few years completely crush an adult in a tournament who has played the game for 10x the number of years.



When I got to MIT, I stopped playing chess. I had a lot going on, and I just didn’t have it in me to do what felt like banging my head against the wall that was blocking my progress. Plus, with two majors and two jobs, there really wasn’t any spare time.

I started playing again last year. My two older kids hadn’t shown any interest when I tried to teach them chess. But my youngest, Jacob, was very much interested, even when he wasn’t quite five yet. What’s more, he seemed to have a natural ability, and was improving rather quickly.

This brought back memories of Dvorets Pionerov, and of being told there was no room for me in the chess school. I promised myself that if Jacob was interested in learning, I would do everything that I could to give him the opportunity to learn chess the right way. The opportunity that I didn’t have.

So I decided to get back to learning chess myself. Playing chess is easy, but it doesn’t necessarily lead to any learning. You can play chess for decades and show no improvement. I have met many an old player stuck at the same rating achieved and quickly surpassed by children who were seriously studying chess in a small fraction of the time.

Learning chess takes dedication. You have to build your chess up, brick by brick. Slowly. You have to spend a lot of time on learning and practicing concepts. Studying the games of great players. Reviewing your own mistakes, even in games that you won.

Learning chess is hard. Especially as an adult. Particularly as an adult with three kids and a full time job. But it’s worth it to me to share this journey with Jacob, as long as he is interested in pursuing it. It allows us to bond over something we both like, and hopefully progress together.

My stretch goal for myself in chess? To become a master by the time I turn 50. I have my work cut out for me, and if Jacob continues to seriously study, he is likely to become a master before me. Since I teach him chess three times a week, I asked him if he would be willing to give me lessons three times a week once he becomes a chess master. Jacob cocked his head, thought about it and replied “No Papa, I think I will be too busy for three times a week, but I could probably do two.” Ah, the honesty of a five year old!

What does any of this have to do with investing? What I didn’t have learning chess, I was fortunate to have in learning investing. I started at an early age. I learned from a great master. I built my process, brick by brick, on a good foundation. I have continued to gradually improve as an investor for over two decades. I have made many mistakes along the way, and seen many mistakes made by others. I learned and improved by virtue of those mistakes.

What I see in many who try to invest is the same set of problems that I encountered trying to learn chess. There are plenty of books, written by authors with fancy titles. There are many areas one needs to learn, such as accounting, business analysis, how to size up a management team and how to value a company to name but a few.

Just like in chess, merely doing doesn’t lead to mastery. The old joke about an investor who doesn’t have 20 years’ worth of investing experience but has one year of investing experience twenty times is right on the money. What’s worse, the feedback loop is long. In chess, when you lose a game you know you deserved to lose, and you can quickly learn from your mistake. In investing, the feedback loop between decision and outcome sometimes takes years. And in the meantime there is the stock market noise that frequently sends false signals of unearned success or temporary failure to confuse the aspiring investor.

There is no quick path to investing mastery. No matter how much potential or aptitude you have, without a long stretch of sometimes painful experience those are not enough. All the book knowledge in the world will not make you a master investor without years of deliberate practice and study. You have to build investing mastery, just like chess mastery, brick by brick, slowly and deliberately over the years.

It’s a hard journey that few will make. The rest have two choices. Know yourself well enough to know that you aren’t there yet, and invest accordingly. Or succumb to the hubris of many market speculators and think that you know how to invest when you really don’t. The latter could be an expensive choice.

 

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