The Chess Bug: Life Lessons Learned Through Chess

I’m staring down at the rickety wooden table covered by 64 squares and 32 pieces in Chess Forum, New York’s iconic old-school chess parlor. Located in Greenwich Village, just blocks from Washington Square Park.

The whole parlor has that “old book smell,” the smell that makes you wonder who else has wandered the same room. It turns out, the answer includes American chess legends like Bobby Fischer and Fabiano Caruana.

My schoolwork is shuffled off to the side, and my vision is centered on the pieces in front of me.

In the last 72 hours, I’ve thought of almost nothing but chess. 

Two hours later I walk through Washington Square Park and observe games between the “hustlers” and a local Manhattanite at the board.

“Spectating isn’t free” the hustler yells at me as his position grows worse and worse against an evidently strong player.

I keep walking toward the park’s fountain.

 A man in a black top hat struts along in my direction before quickly turning north. For just a moment, my brain confuses him for a knight: moving in an L-shape.

The world around me has become a chessboard. I’ve caught the chess bug once again. 

It’s not the first time my brain began to confuse the real world for a measly board game.

The first time was in 4th grade. As the big dogs of elementary school, we were allowed to stay in our classroom for lunch. And I did. Every day. At the intersection of two oval tables stood a chessboard.

I don’t remember many games, but I remember one los against my teacher.

“Hey Dave, you just got scholar’s mated,” Mr. Driscoll, a football coach in his 60’s with shaggy, curly hair said as he beat me in four moves. “I expect you to be better next time.”

It’s hard to say how good I got playing in lunch five days a week for a whole school year. But I don’t think I was particularly good, even for my age. I have no recollection of studying endgames, or checkmates, or opening theory. I was just a boy and his brain, learning the game without resources.

As I moved on to middle school, and other interests attracted my attention, I forgot about chess.

Six years later, my sophomore year of high school, I joined my school’s economics club. Not because I cared about economics, but because “econ club” often turned into more time spent playing mini basketball, and, that’s right, chess, than learning about supply and demand or whatever.

(although we still won the state championship, a testament to our general knowledge more than anything else, and a story for another day.)

I saw our econ teacher Mr. Alofsin duel out over the chessboard with some of the smartest kids in the school, usually coming out on top.

I jumped in for a few rounds, digging up standard strategies I used in 4th grade and my general cognitive awareness to not make stupid mistakes. I lost.

This year also happened to be my first year of junior hockey. In order to play junior hockey that year, I had to leave school at 12:45 four days a week to make it on time for the 1:45 practice in Burlington.

When hockey season ended, those extra hours at the end of the day turned into study hall time. In that study hall, a few of the Econ club chess players also played.

And I mostly kept losing. To the good players anyway. It was only a few months earlier I’d first read The 48 Laws of Power by Robert Greene. I recalled a chapter on Bobby Fischer, the only American to win the world championship. Remembering that story, I bought “Bobby Fischer Teaches Chess.”

I dug into the book, learning tactics and strategies from Fischer himself.

In those extra two hours a day, I studied Fischer’s book and played more chess. When I wasn’t playing, I was reading about it, studying puzzles, understanding tactics, opening theory, and endgame principles.

I knew what “development” meant, the importance of “castling,” how to look for tactical weaknesses like “forks” and “skewers,” exploit strategic weaknesses like “isolated pawns,” and take advantage of positional strengths like “passed pawns.”

In the evenings I played games online on my iPad. In the mornings I watched grandmasters play and give lessons on YouTube while I ate breakfast.

Soon, everybody in high school who once seemed like a great player, the product of a deeply analytical and logical mind, made mistakes I now recognized as obvious.

After a few months of study, I played Mr. Alofsin, the best chess player I knew. His chess-playing abilities were a product of sound thinking: he was logical, tactical, and aggressive.

I started this game with the King’s pawn opening: pawn to e4. By abiding by the “opening principles” I learned in books, I came out with an active position where my pieces occupied important space. Within a few dozen moves, the tactics opened themselves up because of my pieces’ activity, and soon I was in a simple endgame.

“Rosales,” Mr. Alofsin sighed as he knocked over his black king, “This game was over as soon as you picked up a chess book.”

The More I Studied Chess, The Better I Got

Books meant progress. Learning meant progress. While reading helped me grow in other areas, such as acquiring the knowledge necessary to become a better hockey player, or even in a more nuanced way taught in The 48 Laws of Power I had never seen such immediate results from books.

The message, although it never hit my conscious mind, was clear: if you want to get good at something, read about it.

Over the summer, I kept playing. I had a few friends who studied the game as a hobby as well. 

We went to each other’s houses and played some of our most inspired chess, looking for small advantages, applying what we were reading about.

I played on hockey road trips on an old magnetic set, generally smashing everyone who wanted to play against me.

For our team’s secret Santa, my teammate said this about my gift:

“Well Rosie loves to read and play chess on the bus, so I got him a book about chess.”

The Book: The Art of Learning by Josh Waitzkin.

I’ve written and spoken about the impact this book has had on my life.

In the book, Josh, considered a chess prodigy in his youth, recounts his journey to demystify the art of the learning process through the mediums of chess (he’s an international master), and later tai chi push hands (he’s a world champion.)

At this point, it may sound like I was some great chess player. I assure you, even at the height of my obsession, I was still a high beginner/low intermediate. Becoming an elite chess player takes years of daily, intense study.

I was playing for a few hours after school and reading some books.

But even though I didn’t have the years and years of study to understand the nuance of positions, the tactics to watch out for in certain games, the repetitions necessary to truly be good at anything, I played it at a high enough level to conceptually understand the game apply the concepts to my other areas of my life.

I deeply value interdisciplinary learning, the ability to make connections across fields, to draw on them all, and come up with something unique.

In Waitzkin, I saw a mirror for how my brain works. 

He wrote about how, when he was practicing tai chi, he felt like he was playing chess, and vice versa. He saw how the lessons from each field overlapped, and strengthened his ability to do both.

When Josh wrote about the importance of mastering the endgame first, of learning the intuitive power of the pieces on their own before throwing them into complex environments like openings, I thought about how in training on the ice I was thrown into breakouts, and systems, and drills, when I what I really needed was to step back and work on my stride: the foundational power of my “pieces” was the ability to skate.

Years later, as I trainer, I thought about this lesson in the context of teaching exercises. Where are we adding on unnecessary complexity? You have to learn to goblet squat, split squat, do push-ups, and sprint before you worry about rep ranges, tempo, and advanced exercises.

Start with the endgame, I learned through chess. Learn the intuitive power of the building blocks before moving on.

As I read and reread The Art of Learning, I realized I was no longer obsessed with learning opening theory or endgame strategy.

Instead, I was obsessed with using the concepts from chess and applying them to other areas

It was the book that put words to how learning transcends fields, that opened the door for me to verbalize one of my greatest strengths: the ability to make connections across disciplines.

I played throughout high school, competing and finishing top 10 in the scholastic chess tournament my senior year.

I even played at the local library weekly during the spring of my senior year with an old chess master who was too deaf to hear me and could hardly see the pieces on the board.

At his advanced age, I was able to muscle out some draws. We played with no clock. Our games lasted hours. He could take up to half an hour to make a move, and I the same.

His son, about 50 years old, would come to check in on us, give us snacks, and express his gratitude for playing with him. I learned how to maintain concentration, as chess gave me an incentive to get become really good at meditating.

Now, I sit in the Chess Forum on the perfect fall New York City day, where Fischer himself poured over the bored, playing a blitz game against a fellow member of the chess parlor.

I spot a creative sequence that sacrifices a bishop for a potential mating net. Without the time (or rather, the skill) to work out whether it leads to mate, I jump into the attack, channeling my inner Beth Harmon or Paul Morphy (a real-life world chess champion known for his cunning aggressiveness). My queen, knight, and a marched pawn are closing in.

Then, my opponent moves a pawn in front of his key one square, opening up the path for his rook to swipe in and defend just in time.

My attack crumbles, and I lose the routine endgame.

0-1 is all the scorecard says. But life, unlike chess, doesn’t have a scorecard. Because that attack, although futile, stemmed from a creative burst.

I leave the board with my head held high, ready to channel the excitement of a blitz chess game into something more. An article, a conversation, an experience in life. 

I will never play chess like Magnus Carlsen, Bobby Fischer, or even a run-of-the-mill competitive chess player.

But, whether I’m playing the chess hustlers in Washington Square Park, at the chess parlor on Thompson Street, or on my screen on, I’ll take those 64 squares, grow them to life-size in my mind so I stand like a king on his square while the rest of the pieces roam the squares on New York City’s streets, turning my whole life into a chessboard.

More chess reading:

In the spirit of the explosion of popularity of The Queen’s Gambit, I wrote a whole article for Roman Fitness Systems (where I put most of my fitness writing these days) called Fitness Lessons From The Queen’s Gambit.

I also wrote on of my most popular recent fitness articles on how “Overprotection” in Chess can help you build better habits.

I’ve also written a few Instagram posts about lessons from chess that can make us all better learners.


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