My buddy and I started playing chess regularly during lockdown in 2020. We were both competitive and couldn’t leave the house, so we battled on the 64 squares online.

He was better than me. I hated it.

It became my life’s purpose to reliably beat him. That summer, we were both around 1000 ELO. Grandmasters are rated around 2500-2800 ELO.

Since then, I…

Played in tournaments with my friend, with both of us winning trophies and cash prizes.

Played in tournaments by myself, getting absolutely destroyed.

Went head-to-head against chess hustlers in Washington Square Park.

Bullied children.

Hired a chess coach. (In this lesson, he played me blindfolded…and won.)

Interviewed Eric Rosen, my favorite chess YouTuber. I’m writing a chapter about him in my book.

Studied chess puzzles and practiced almost every day.

Started a chess club.

Analyzed my games—looking for mistakes and checking out other possible lines.

Played whenever and wherever I could.

Got to 1300.

Got to 1400.

Got to 1500.

Climbed and climbed in 2021.

Got to 1600 before plateauing for the entire year of 2022.

And after being stuck at 1600 ELO for a year, I’ve finally broken through to the next level. On January 1st of 2023, I surpassed 1700 rating points.

Here’s the graph of my chess journey these past two and a half years. Notice the stagnation between December 2021 and December 2022.

They say it’s around 1600 ELO where a player can’t just increase his/her rating by playing more games. It takes study and game analysis. What got you here won’t get you there.

It was frustrating. I had to confront the humbling reality that much of my love for chess was my constant and visible improvement. When that improvement stopped, I had an identity crisis. I thought about quitting the game entirely more than once.

But cooler heads prevailed. I kept solving puzzles, seeing my tutor, and playing in tournaments despite the resistance.

I believe in cutting out draining and unfulfilling activities. But it’s wildly important to grit through something when it doesn’t feel exciting. We have to know if we can make it out to the other side.

Martial arts. Playing an instrument. Learning a language.

The image of being really good at these things is gorgeous. But the road to get there requires hours of mundane and tedious practice.

I don’t feel like going to most of my chess lessons, jiujitsu classes, or workouts. But the comfort level of a thing says nothing about our ability to do it. And more importantly, once we actually get going, much of that initial resistance fades away.

I’ve never regretted a workout or study session. But I almost always regret skipping one.

Anyway, let’s wrap this up.

My driving force in my early chess career was beating my buddy. That was all in good fun. I’m grateful for our rivalry because it kept me coming back.

But along the way, our games became just one of the many reasons I love the game. I see chess as a perfect cocktail of science and art. I love watching chess creators on YouTube explain games and play at high levels. I just signed up for my first international tournament in Argentina when I move there.

Maybe 1800 ELO will take me another year. Maybe two years.

It doesn’t matter. So long as I’m finding new ways to enjoy the journey. The only thing that matters is staying in the game.

Yesterday was the quarterly Baltimore Charm City Chess Tournament. I played in the U1400 section.

Typically, I compete with my buddy. But he was on a work trip so I was left to my own devices.

I got to the hotel early, as I always do. After signing in and dropping off my bags (my chess set and food), I took my usual stroll around the Johns Hopkins campus.

It always gives me anxiety walking on a college campus. It brings me back to my days of skipping class and feeling low status. Sometimes I feel insecure pacing by students as a 28-year-old man with a mustache.

But it was a lovely day. The air was crisper as fall approaches.

When it got closer to 10:30 I headed back to the hotel to see the first pairings. My first of five opponents was a teenager with a lisp.

Shit.

In the first game in my last tournament, I played against a four-year-old and nearly lost. I’m not proud of it, but losing to a kid has a particular sting to it.

But this teen was good. He slowly squeezed me until I blundered a piece and resigned. After losing, my mind flooded with excuses.

I’m tired. It’s not as fun without my friend here. I might leave early and enjoy my Sunday.

Fear of failure leads our minds to hilarious places. I texted my buddy, “Never again will I do a tournament by myself.” I was so salty!

If you’ve ever climbed a mountain or worked on a difficult project, you know this feeling.

Starting or launching a pursuit is exciting and novel. We have these shiny images of what it’s going to be like. Then we get going.

Nine times out of ten, it gets hard or boring or both. We have to push through resistance. We need to improvise and solve problems we didn’t account for.

At some point, we even question why we wanted to do this thing in the first place. That’s where I was at. All I could think about was losing my remaining four games.

But I stayed.

In game two, I demolished the poor guy and he resigned after 13 moves. Chess was fun again.

I texted that same friend, “Nvm just beat a guy in 13 moves my spirits have lifted.”

It’s wild how easily our states can change. It makes me question reality. How much of our perceptions of what is going on are painted or tainted by how we feel at that moment? I went from genuinely hating chess to being eternally grateful for spending a day playing my favorite game.

With my newly-found momentum, I won the rest of my games—tying for second place and winning $100.

The winner and I played in my first-ever tournament last winter. We drew. I saw him and congratulated his performance.

These events always pump me up to improve my game and play more. If you’d like to see my actual games, here’s a link to a study I made. I even annotated some of them so you can see my thought process.

Having hobbies and activities that have nothing to do with work or money is rewarding and therapeutic.

What are your favorite things to do outside of work? Let me know.

(PS—Here’s my favorite final position from round 5. It’s rare to have the enemy king so deep in your own territory.)

Today, my buddy and I are competing in a chess tournament.

It’s organized by Charm City, the chess club that put on the first one we did in December. That went well. I got third place.

Then, a few months ago, I had a chess-existential crisis. I wanted to quit. I played another tournament and hated every second of it.

Now, with my new and improved mindset, I’m going to spend the day with my friend and try to have as much fun as I can.

I’ll shoot for open, tactical, and dynamic play. I’ll try to meet people. I’m excited.

I’ll tell you how it went on Monday.

January was a rough month for my chess career.

It was the first time since getting into the game in 2020 where I just didn’t feel like playing. It wasn’t fun. That scared me.

Was this all just a phase? Was my fling with chess over?

I trudged through my chess workbooks and daily puzzles. But I wasn’t enjoying it.

Then I got my ass beat in a classical tournament. I lost three out of three games. Coming off of a tournament in December where I got third place…it was crushing.

I went from thinking I was hot shit to wondering if I should ever play again.

But it wasn’t the awful tournament that made me unmotivated. I felt that way before the event. Why then? I spent over a year consistently amped to log on to chess.com and play every single day. And now I didn’t even want to look at my board.

What changed?

Then it hit me.

In chess, each player has an ELO rating. It’s a number that basically tells you how good you are.

When I started playing over quarantine, I was around a 900. Now, I’m around 1650. Grandmasters, the best players in the world, are close to 2800.

From December 2020 to November 2021, my ELO steadily increased. Every few months, I’d be another 100 rating points higher.

Now, I’ve hit a ceiling.

My rating hasn’t increased at all in three months. It’s the heaviest plateau I’ve experienced.

My insight was: Most of my fulfillment in chess has come from my increasing rating. That’s not sustainable.

It’s well-known in the chess world that once you hit 1600, you’re considered an advanced player. At that stage, it takes much more serious studying and practice to improve.

I felt silly. If I expected my rating to continue climbing the way it had been, I’d be a grandmaster in the next five years. That’s actually impossible.

So if my unsustainable, ego-driven path landed me in a rut, what can I do now?

Well, I decided to change what I wanted out of the game. It sounds corny, but I made the decision to just have as much fun as I can when I play.

I changed my style entirely. I began playing a different opening. Before, I focused on slower positional play. Now, I go for more open and exciting tactical play.

It has led to more losses. But it’s also led to more dynamic and flashy wins.

My passion for chess feels immediately revitalized. In the coaching world, we say: What got me to this level is what will keep me from getting to the next level.

What got me to this level: Caring deeply about how good I was.

What will get me to the next level: Having as much fun as I possibly can whenever I play. (And studying and analyzing and blah blah blah.)

My buddy and I have another tournament coming up next weekend. I’m pumped. 😎

I played in my second chess tournament this weekend. It didn’t go well.

My first competition was in December. That one went much better.

In typical fashion, I showed up an hour early. I was the first one there. I met the head of the Waldorf Chess Club and we chatted about chess and sandwiches.

The other players piled in and we got sectioned into quads: groups of four. We would play each person in our quad once for a total of three rounds. I took math in college so I put this together quickly.

To spoil the whole thing, I lost all three of my games.

Here’s how each of them went:

1. Neck and neck until he ruined my pawn structure (weakened my position). Beat me in the endgame because of my bad position.
2. I tried to be crazy flashy and sacrificed two pieces for a fancy checkmate. I miscalculated and was then just down two pieces.
3. A super even game that went down to the last few minutes. He was up a pawn and used that to beat me in a King and pawn endgame.

Here’s what I took from all this.

Losing sucks…

But it is valuable. For many reasons.

After a strong performance in my first tournament, I thought I was hot shit. I needed to be humbled to snap back to reality. Mom’s spaghetti.

As I learned in Brazilian Jiujitsu, being humbled, getting your ass kicked…It makes us kinder and more patient people. It gets us out of our heads. It destroys our egos. Our wellbeing stems not from our success, but our willingness to grow.

Only when our armor is damaged can we begin to make repairs to it. Otherwise we just walk around thinking we’re invincible.

I barely remember the winning moves I made during my first tournament. But the losing moves in this last one are engrained in my psyche. I can envision them right now as I’m typing this.

It’s an unfortunate truth, but losing is the best (only) way to get better at chess. That’s probably true in any endeavor: business, relationships, instruments.

When I meet with my chess coach next, we’ll have plenty to analyze.

The people I played this weekend were much stronger than those I played in December. It was a reminder that I must consistently go against better players.

The first competition pumped me up to improve at chess. It was a Winning is fun! I want to do more of it kind of motivation. This one energized me even more. But this time it’s a Losing is awful! I want to do less of it sort of thing.

The losing will never stop. It’s part of leveling up. It’s out of my control.

The only thing I can control is what these losses mean for me.

Back to the drawing (chess) board.

I’m about to leave for the Waldorf Chess Club’s Quads #45 Classical tournament.

If you’re wondering what some of those words mean…me too. But it sounds quite impressive.

In December, I played in my first competition and did well. This one will be much more challenging.

You’ll notice I’m in the lower tier of players. That’s just my provisional rating, but it’s still hard not to let it affect emotions and expectations.

Today we play three games (rounds). They will be the longest games I’ve ever played—70 minutes for each player, 10-second delay. That means each game could take two to three hours.

The first round starts at 10am, the second at 1:30pm, and the last at 4:30pm. Long day.

I feel I got spoiled in December by not losing a game, which means I’m undefeated in my chess career. I’m not planning to lose today, but I’m emotionally prepared for it.

Playing better players is the only way to improve. So I’m excited to make some blunders and analyze my games with my coach.

Wish me luck.

On Monday, I’ll tell you how I did.

My friend and I played in our first chess tournament this Saturday.

It was one of my favorite days ever. Not because of any result, which I’ll get into. But because of how fun the experience was. Let me explain.

1) I got to spend the day doing something I love with one of my best friends.

We got there an hour early. That’s my style. For any event, I’d rather be an hour early than a minute late.

We settled in, validated my parking in the Hilton garage, and prepared.

My buddy brought a couple books and his laptop to do some last-minute studying. I took a different approach.

Since the hotel was right across the street from the Johns Hopkins campus, I took a 30-minute stroll. It was gorgeous.

I walked past their cafeteria, quad, sporting facility, as well as the largest gym I think I’ve ever seen.

I wasn’t thinking about chess at all. I was meditating over how cool it was to finally be competing in this thing I fell in love with over the past year.

It was refreshing to clear my head. I didn’t think twice about not doing any last-minute studying.

Before a big fight, a reporter went into the locker room to find Floyd Mayweather playing Xbox. He said, “Aren’t you going to warm up for the bout?”

Floyd glanced over and smiled. “If I’m not ready by now, I’m not ready.”

Yes, I compare my chess playing to the greatest boxer ever. But that’s how it felt. I was as ready as I could be. And that made me feel totally present as I floated by those Hopkins students.

2) We got to nerd-out with other chess peeps.

This tournament broke the Baltimore record for the largest private chess competition. There were 96 registered players. 51 were competing in my section.

Everyone was so kind. Between rounds, we could see almost every table in the lobby with a chessboard on it and people analyzing their last game or playing blitz.

It was cool to know that everyone in the room enjoyed chess so much that they too signed up to play in a tournament.

There were four rounds (games). We had a 30 to 60-minute break between rounds to eat, chat, and chill. Then the next pairings would post and we’d make our way to our tables.

For more than half of the players, it was also their first tournament.

Each round, you got paired up against someone with the same record as you. That way one would hopefully play people closer to their skill level. It also meant that each round got harder…and more fun.

3) I played well.

My first game was against a 13-year-old kid. I felt bad.

He was clearly newer to chess and I obliterated him. Starting out with a win boosted my confidence but I didn’t want to get complacent and expect each round to be that easy.

My friend lost his first game, unfortunately. He got paired against a pretty good player.

In Round 2, I got placed with another player who was 1-0. He was a super nice 20-year-old who drove down with his two buddies from Harrisburg, PA.

He was much better than my first opponent. But over time, I was able to chip away at his kingside, win his Queen, and be up so much material that he eventually resigned.

I could see him get visibly frustrated with himself during our game. We shook hands and wished each other well for the remaining two rounds. My buddy also won his game.

I was most nervous for Round 3 since I assumed my opponents would only be getting better. I was correct.

My third opponent was a calm and quiet guy with long hair. It was also my first game with the black pieces, which meant I moved second.

That was one of the most intense games I’ve ever played. I pressed him, then he pressed me, then I broke through. Then he blundered a piece. I was winning. My heart was pounding. Then…I blundered a piece! We got back to an even game and he got me in a perpetual check. We agreed to a draw.

I was kicking myself a little for not converting a won game. But I was mostly just happy I didn’t lose. A draw is .5 points. I was 2.5/3. My buddy, who lost his third game, was 1/3.

Last Round.

For whatever reason, this was the first game where I wasn’t nervous. Maybe it was because I was exhausted. We got there at 10am and it was now 4:30pm.

The guy was talkative and kind. I thought he would be my toughest opponent. But I won his Queen in 11 moves.

After that, I started trading pieces and chipping away at his defenses. I had checkmate in two so he resigned. He was pissed.

I felt bad because we were the first ones done out of 26 games. I was relieved to be finished and thrilled I didn’t lose a game.

I finished 3.5/4. My friend won his last game to go 2/4.

What this means.

To my surprise, I got third place out of 51 players. That obviously felt good.

It also means I now have a professional record in chess. I have a provisional rating of about 1400. That’s like a rating with an asterisk.

Once I play 25 games (21 to go), I’ll have my actual rating.

Last night, I signed up for my next tournament—The 59th Annual Baltimore Open. It’s next month and the players should be quite good.

But for now, I’m celebrating a phenomenal start to my chess career. I played well, got some hardware, and had a blast with my good friend.

What more could I ask for?

Last summer over quarantine, one of my best friends and I started playing chess together online.

It was just something competitive we could do while trapped in our homes.

I knew how to play from years prior, but had never taken the time to learn the game’s basic principles, strategies, or tactics. Now, I had a mission—a purpose.

To beat my buddy.

He was better than I was so the bitter taste of defeat was a powerful motivator to improve. My ELO (rating) was around 900.

We got super into it for a few months until I fell out of love with the game entirely. I looked at a board and couldn’t care less what happened on it.

Then I, along with 62 million other folks, watched Queen’s Gambit.

The show single-handedly increased awareness and interest in chess tenfold around the world. Chessboard sales skyrocketed. Chess streamers and commentator channels had enormous boosts in their following. I was a part of all these statistics.

Then something strange happened which improved my chess skills tremendously.

I got Covid.

For the first time since starting my own business, I took a week off and did nothing but order DoorDash and play chess. Five to ten hours a day.

My rating went up 100 points in four days.

Since then, I’ve played consistently online, read books, analyzed games, hired chess tutors, and spent hours watching my favorite YouTubers go over games and teach. Here’s my rating in 2021:

Today, that same friend and I are playing in our first over-the-board tournament in Baltimore.

I’m excited and proud of how far we’ve come in a year. I’m nervous to lose to an 11-year old kid. And I’m grateful to share one of my passions with one of my closest friends.

We play five games in six hours. It’ll probably be exhausting…but I’m so pumped.

On Monday, I’ll post about how it went and what I learned from the experience.

Wish us luck. 😊