Having played a total of 100 hours of live chess games online over the past six months, I reflect on some general lessons learned by drawing parallels between playing chess and running a business.
This writing is intended for a general audience, not just chess players. For context, I started at a 400 Elo rating (23rd percentile) on Chess.com six months ago and recently reached a 1000 Elo rating (80th percentile), marking the transition from beginner to intermediate. Some exceptional learners achieve this in just a few weeks, while others might take years or never reach 1000. From what I’ve gathered, active players who are consistently learning and improving typically reach this rating within 3 to 8 months.
Intro
Before we continue, let’s rewind to when my new hobby started. “Daddy, I want to play this!” exclaimed my 5-year-old daughter after receiving a travel chess set from a friend for Christmas last year. So, I looked up the rules, and we began to play. It had been probably three decades since I last played chess as a 4th or 5th grader, and almost all my chess knowledge had escaped me, except for the names of the pieces. While my initial motivation was to provide some extra daddy coaching to my daughter, who had joined her school club, it turned out to be an addictive, dopamine-inducing pastime for me in the months that followed. With the major chess apps, you can start a live game within seconds at any time of day and be matched with a random stranger across the globe at a similar playing level. Soon, I became one of over 10 million daily active users on chess.com.
Lesson #1: You Can Win by Not Blundering
Blundering is the chess term for making silly mistakes, like leaving a piece undefended or unnecessarily free for your opponent to capture. These are unforced errors. Beginners often blunder by simply being negligent and not thoroughly checking their moves before making them. Unless they are unfamiliar with the rules, in almost all cases, if you asked the player, “Are you sure about that?” they would be able to spot the blunder before making it. My daughter can spot my blunders when she watches me play.
Now an often overlooked truth is that even without fancy moves or tactics, you can often win beginner games by simply not blundering or blundering less than your opponent. Slow and steady can win you races.
The business analogy here is simple: don’t make blunders, and you’ll already be ahead. Blunders such as poor financial management, ignoring market signals, PR disasters, or simply not keeping regular operations in order.
Lesson #2: Take Your Time to Get It Right
Online chess games can be played in rapid, blitz, or bullet formats, with the difference being the total time you get for thinking about your moves. The default timing for rapid games is 10 minutes, which is what I initially played. In my earlier games, I lost many of these due to timeouts, even though I often had winning positions. This time pressure also probably led to many blunders. Later, I switched to playing 30-minute games, where both sides had plenty of time to thoroughly consider their moves. The extra time not only relieved the time pressure but also provided a buffer for unexpected interruptions, such as calls and when I needed to attend to my crying younger baby.
To be clear, I’m not saying you should avoid time pressures completely, but rather to take time as necessary early on if you need it and when you can afford it. In building IT systems, conventional wisdom holds that it’s exponentially more costly to fix bugs and errors in the live production stage than during the development stage. This underscores the importance of taking time to test systems (i.e., akin to checking your chess moves) before moving on.
A related life/parenting lesson here is that you should play at your own pace whenever possible and choose a path or setting that gives you (or your children) the time needed to build a solid foundation. When this is not the default timeframe that society prescribes, consider making adjustments and be open to being flexible. For instance, while Kobe Bryant and LeBron James were top high school players who were drafted directly into the NBA, Michael Jordan, widely regarded as the GOAT in basketball, was famously cut from his high school varsity team and had to develop his skills on the junior varsity team.
Lesson #3: Learn Guiding Principles
In the game of chess, there are openings, which are standard sequences of moves that provide a positional advantage. There are hundreds of openings, each with several lines or variations. Without any knowledge of these and just playing casually in my first 70 games (over the first 2 months), my rating only managed to reach a steady 550 Elo (38th percentile). As I began learning the openings during the 3rd month, I played another 80 games and reached a 750 Elo (59th percentile). While learning, a beginner will inevitably come across various gambits, which are moves that sacrifice a piece to set up a tricky trap for your opponent, often promising to “crush your opponent” 😂. I watched dozens of YouTube videos on gambits, and the extra knowledge gave me enough of an advantage to improve by another 100 Elo, reaching 850 Elo (69th percentile) in just half a month over another 50 games.
All seemed well until my progress started stalling. While openings are an important part of the game, pure memorization without understanding the underlying principles will leave you wondering what to do next after the opening phase. More commonly, a beginner will simply not be able to accurately recall these standard “book moves” after several moves, especially if the opponent plays something non-standard. Stronger opponents also had better responses to my shallow understanding of gambits. Over the next two months, I only played 70 games, and my Elo rating did not improve. I was stuck at 850 Elo, and deep down, I knew that my foundational understanding of the game was not strong enough to progress further. I re-examined my original motivations for playing the game from four and a half months ago and realized that I had gone astray in chasing a vanity online Elo rating rather than learning something meaningful that I could teach my daughter.
So, I went back to the drawing board with my learning approach. This time, I sought out resources to understand chess principles and applied them in practice. I stopped caring so much about the rating. With a new mindset and approach, I was much more confident and felt better about my games. Over the next 1.5 months, I played another 70 games and finally hit an Elo rating of 1000 (80th percentile). In the final month leading up to this mini-milestone, my win rate was 64%, despite playing stronger opponents, compared to 52% over the previous 3 months. Most importantly, I was able to distill what I learned into simple principles that I taught my daughter to help guide her chess thinking.
The business lesson here is to let solid principles guide your decisions. Ray Dalio provides a valuable set of principles to follow in his book, and this post offers a good summary.
Lesson #4: Truly Understand Your Mistakes
My high school teacher, Mr. Rowark, once said, “Practice does not make perfect. Perfect practice makes perfect.” You would benefit more from playing 10 games and improving from a different type of mistake each time than from playing 100 games where you repeat the same mistake. With Chess.com’s Review Game feature, you can analyze your games move by move, compare the quality of your moves to what the best move should have been, and even simulate continued play starting from any position at any bot difficulty you set. However, even with such an advanced tool, it’s often not immediately clear to me why the computer considers a certain move to be best, especially when there is no immediate threat and the implications of a move aren’t apparent until several moves later.
Most people know that they should learn from their mistakes in whatever they’re doing. But you can’t learn from a mistake if you don’t fully understand it in the first place. Worse yet, sometimes you don’t even realize that you don’t fully understand it until you’re lucky enough to have someone point it out to you.
Many years ago, I attended a customer meeting to pitch my products. At one point, the customer seemed perplexed by the prices I quoted and began grilling me on my entire model. A seasoned distributor himself, he proceeded to lecture me on pricing segmentation, sharing several real-life cases he had dealt with involving household names in our market. I re-examined and changed my pricing approach afterward.
On another occasion, a customer asked me about our paid search ads. I proudly told him that we already ranked high organically and didn’t need paid ads. “Are you serious?” he responded, then educated me on why ranking high organically alone was insufficient.
Try to find coaches or mentors for different aspects of your life, or at least seek honest feedback from more experienced people.
Lesson #5: Secure a Relative Advantage
“You missed the opportunity to win a pawn.” This frequently appearing Game Review feedback initially puzzled me a lot. I didn’t understand the big deal about a pawn, the lowest-valued piece in chess. In fact, sometimes I wasn’t even dealing with a pawn in a particular exchange. Furthermore, the best move often involved trading queens with the opponent, and I would wonder why losing your most powerful piece was the best move. Then, after playing enough games, I understood why, and I think this is best explained with a sports analogy.
Imagine a soccer game between two equally strong teams of 11 players. If a player gets fouled out and they have to play with one person less (10 vs 11), it’s, of course, less favorable but not an immediate game-losing predicament. Now imagine a crazy game where each side continues to lose players until one team only has one player left and the other has two! Surely, the team with two players would have a significant advantage, even though the absolute advantage is still only one player. In chess, when a game reaches the endgame phase, it’s quite common for a player with only a single pawn advantage to win the game. This is why in chess a common strategy is to “trade down,” or make even trades when you are leading in material, to gradually turn a small absolute advantage into a significant relative advantage.
In business, if you can establish and sustain a relative advantage over your competitor, however marginal it may be, the effects of that advantage can compound over time, potentially leading to a decisive win in an absolute scenario.
As for trading queens? By removing the most powerful piece from both sides, you simplify the game and reduce your chances of blundering. Let’s look at a fun example. Imagine playing a full-court basketball game where your team has a one-player advantage, so you have 5 players while the other team has 4. Your team’s chances of winning are quite high. Now, imagine that both rec teams each get an NBA superstar—your team gets Kobe and the other team gets LeBron! Suddenly, even though they’re one player short, the winning chances isn’t so clear-cut. If your primary goal is to win the game (rather than just enjoy playing with the superstars), removing both superstar players would eliminate any surprises and solidify your one-player advantage.
Lesson #6: Prioritize Execution Early On
Chess tactics are short-term move combinations (within a few moves) that help you gain an advantage, while strategies require a deeper understanding and a more holistic view. Honestly though, being a beginner player myself, I can’t say much at this point about any advanced chess strategy. This is also a commonly held notion about beginner’s chess—that games are mostly won through good tactical play and avoiding blunders.
In business, I would relate tactics to day-to-day execution. Having an overarching business strategy is important, but irrelevant if you can’t execute it well. This is especially true for startups and smaller businesses, where execution and hustling (drive, determination, resourcefulness) are what determine whether your business lives and grows. Once you are able to build a solid foundation through tactical execution, you can then focus on refining and expanding your strategy to ensure long-term success and scalability.
Conclusion
Over the past six months, my chess journey has revealed and reinforced some valuable lessons applicable to both business and life. If you’ve read this far, I hope these reflections provide some inspiration and practical wisdom.