What I learned being frustrated as an amateur chess player

During the covid-19 pandemic, I played my first online chess game. I created an account on chess.com, and within minutes I was playing a match with some other random player. I got crushed. My journey with reacquainting myself with chess provided insight into dealing with mistakes even with perfect information.

Coming back to Chess

I had played while I was in elementary school, and occasionally I play with my coworker before covid. We had a chessboard between our desks, and oftentimes these games would last days as one of us would make a move between meetings or after wrapping up a task and had a minute or two when we needed a break from our day-to-day. We both won about 50% of the time, which made this so fun. Neither of us had the edge over the other, and we got better slowly over time. However, this did not prepare me for the onslaught that was online chess.

When you create an account on chess.com, you will start at an Elo of 1200 if you choose beginner as I did. Elo is a way to determine your ranking compared to others. If you win against Elo higher than you, your Elo goes up; if you lose, you go down. How much it moves is determined by several factors. If you lose against someone with higher Elo or win against someone with lower Elo, your Elo will be less affected. 1200 on chess.com is different from Elo of 1200 with FIDE, the most popular chess rating. 1200 is quite high and would mean you are already better than most people on chess.com. I think chess.com’s initial ranking is definitely optimistic. Putting yourself as a beginner will immediately catapult you to around the 80th percentile. This means that you are now higher rated than 80% of the accounts on chess.com. Although many of these other accounts may be people creating new accounts to learn or play casually with friends, the 80th percentile still seems too ambitious for someone who has labelled themselves as a beginner.

After a few days after creating the account, I had dropped from 1200 to around 700. I was playing blitz because it was fun to spam out a bunch of moves in 5 mins and see where it took me. In addition, I developed my ability to see tactics in chess. After I dropped to around 700, my rating was starting to stabilize. I have reached my “real” Elo and won about half my games. I stayed here for a few days and then started to go back up. I practiced daily, and after a few months, I picked up some books and got a paid subscription on chess.com to analyze as many of my games as I wanted in detail. I switched to rapid (longer clocks per player) instead of blitz as it gives me a bit more time to think about how to prepare my strategy. I was able to climb to around 1400 in rapid, which is around the 94th percentile. While that may sound impressive, my global ranking is still more than half a million, meaning that there are still more than half a million chess.com accounts with a higher rating. From this perspective, I still have a lot of room to grow.

Lessons Learned

From this experience, I learned two main lessons. The first lesson and the more obvious one, practice daily if you want to improve in something. Make sure that practice time is spent learning to improve your understanding of chess and not just mindless moving of pieces. The books and paid subscription extended my ability to learn on my own aside from only playing games.

The second lesson is about facing unintended mistakes. This lesson was the more insightful and difficult lesson and came in three main parts.

  1. Keeping my composure when making a mistake or blunder within a game
  2. Keeping my composure when giving up a lead within a game
  3. Collecting myself after losing a game while holding the winning position

Losing to a superior player is common, and few of us would get upset about losing to a player that had the advantage from beginning to the end. “They were just better,” we would convince ourselves. The frustration surfaces when we seem to control the situation between a silly mistake and losing the advantage. These kept me up at night at the beginning of my chess journey. I was too invested in this hobby to be throwing away advantages at least once every few games. I looked back at the analysis board and found that I usually had a sizable advantage in most games as I focused on a few openings and got quite familiar with them. However, during many games, I would make a move that seemed fine while playing the game but would lead to disaster. As soon as I go through the analysis and the computer would tell me where the mistake was and what I should have done instead, it instantly becomes obvious why my move was terrible. Sometimes, I would see the mistake as soon as I made it, even before my opponent had the chance to respond. This led me to lose control over my emotion, and I would play even more poorly.

The second lesson is about facing unintended mistakes. This lesson was the more insightful and difficult lesson.

After several months, I started following some major chess tournaments. Watching chess Grandmasters comment on games in real time allowed me to peek into how chess experts look at the board. This gave me insight into what to focus on and what to look out for. For example, I remembered watching one of the games featuring Magnus Carlsen, the world champion, and during this game, he missed a mate in 2 that was obvious enough for me to spot it during the game. He was not under too much time pressure (almost 2 mins is ample time for a player of his calibre), and from his reaction, you can see that he found the mate in 2 almost right away. After he missed his winning opportunity, the computer and the commentators said it was likely a drawn position (meaning that the game should lead to a draw). However, Carlsen was able to come back and win the game. This ability to collect himself and take back control was incredible. He brushed off his frustration and continued to press forward, even with a clock disadvantage.

We put too much pressure on ourselves for deterministic games. We think that the better player always wins and make a big deal of it when it doesn’t happen. However, there is more consistency in men’s tennis than chess. The top tournaments generally feature the same three winners in the past two decades. Although different cultures will have different past times, in North America, chess is generally much less popular than board games that have some aspect of luck and less on deterministic outcomes. This includes other deterministic board games such as connect 4, checkers, and Chinese checkers (the one with the marbles). The opportunity to have random dice rolls decide the outcome of such games is thrilling and beginner-friendly. But how much should we really put “luck” at the centre of our daily decisions?

Embrace “Luck”

While it can be frustrating to lose a game that we are completely dominating, the lessons we can learn are far better than the ones from winning that game. When you lose in chess, you will have the opportunity to find the most room for improvement. You can replay the moves that caused you to lose your advantage or the moves that the opponent was able to gain the most ground. You will not only lose games to better players, especially at the amateur chess level. Even weaker opponents will often capitalize on your mistakes and will not loosen their grip on the game. As a result, you may find that you have bad luck in chess. But by definition, luck is something that is brought by chance. And for games with perfect information, that definition of luck does not apply. On the contrary, people put too much emphasis on randomness in highly skilled card games such as poker or Magic the Gathering. However, you will find that the top echelon of poker and MTG players are quite consistent. These players have incorporated luck as a form of statistical analysis and play a part in every decision they make. They minimize the effects of randomness to dictate the outcome of the game.

Even when you have all the information in front of you, you will make mistakes that seem obvious in hindsight. These mistakes can be soul-crushing, as some have been for me in my professional career. Working in software, releases are often riddled with bugs. Many of these are in new features, and customers are usually more forgiving. However, bugs not in a previous software that surfaces (commonly known as regressions) are more frustrating. Those are the ones that the support team will get calls about. For example, two months after I finished my undergrad, I was working on banking software. One day, support received calls that some of our customers were not able to log in. After some investigation, we found a bug with the implementation of some new password rules. I used the wrong method of finding the maximum allowable password length set in the configurations, causing users with long passwords to be locked out of their bank accounts. It was not bad luck, but rather a combination of failing to follow the proper process and poor execution. As any software engineer who ships products to production, I continued to write my share of bugs. Over time, I realized that due diligence and experience had decreased my own production-breaking bugs and not pure luck.

I now look at luck differently and as a measurement of preparation. When approaching a new game or even a new job, look to differentiate some areas in which you can make a difference and what is difficult to control. This piece of advice is usually one of the first when learning any card-based game. Find a way to incorporate chance into your decision; calculate the odds of your moves being successful. You cannot blame bad luck for all your mistakes, just as you have to give some credit to luck for favourable outcomes.



My passion is building cool software products by leading software teams. I write mainly on growing within software organizations and a bit on personal finance.

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Nicholas Kwan

Nicholas Kwan


My passion is building cool software products by leading software teams. I write mainly on growing within software organizations and a bit on personal finance.