Work Less, Obsess More

Published on 2018-07-02


I started playing chess competitively when I was 12 years old. Despite winning the Wisconsin Middle School State Championships only a year later, I did not progress much as a player for several years afterwards. This bugged me. When I was 20, I started my own company, the International Academy of Chess, and started teaching full time. Chess was my life 60+ hours a week. Half the time I taught, half the time I trained.

In chess, there is one number that represents your strength, your rating. A beginning chess player is rated at 100 or 200 points. A person is considered a National Master if their rating breaks the 2200 barrier.

Over the course of the next 3 years, I only gained a measly 51 rating points taking my rating from 1604 to 1655. At that rate it would take me at least another 20 years to even be considered an Expert player (over 2000 in rating).

Something needed to change.

Doing too much

What was I doing wrong?

My daily training plan included at least one hour in each of the following:

Openings Tactical Play (Short Forced Combinations) Strategic Play (Long Term Advantages) Endgame Classic Games (Games played by professionals in the past) Online Play

Despite the fact that the hour distribution is terrible if you want to improve, I made it worse by focusing on several different concepts under each topic during each of those hours. Concepts were diluted and was mostly me going “Uh huh. I understand that”, when I did not understand each concept well enough to apply it in unique situations that were not the exact position in front of me.

I realized that something was wrong. Instead of focusing on several things, I started to focus on only one thing every day. One day I would only train Openings, or maybe Classic Games. Nothing else.

This would give me more time and I could focus more in depth on those openings and learn them more intimately, right?


Instead of having more time, Parkinson’s Law reared its ugly head.

“Work expands so as to fill the time available for its completion.”

I did not use that extra time to learn those openings deeply, I continued shallow learning. My habits did not change.

My Fundamental Mistake

I had made a fundamental error in my thought process, one that I have now seen with many of my students. I had reduced my scope of learning, but had not obsessed about it. I knew I needed to optimize my learning, but was doing a terrible job of it.

“Learning compounds like interest. The more you learn, the easier it is to apply prior insights and lessons to new things.” - Edmond Lau, The Effective Engineer

When I studied my openings, I was not truly trying to learn everything I could about them. I was enamored with them and wanted the results of famous games, but I could not explain simple concepts that defined them.

I realized I needed to make a major change. After consulting with several other instructors and researching how people learn, I decided to do two things:

Spend less time training Obsess about getting things 100% right

Spending Less Time

The first step was bringing my hours studying and training down from 6-7 hours a day to a max of 3 hours. How did I do this?

I cut out what had the least impact on my game and focused on what created the most value to me.

Openings were fun to train. It gave me something to play with, but ultimately, most of the lines that I would study I would rarely see in over the board play.

Additionally, studying Classic Games were fun, but they did not provide much value outside of key positions and ideas in those games. Most of those ideas would be covered in my Strategic or Tactical training.

And Online Play was fun, but I was not spending time reviewing those games with someone of greater strength. The value being returned was minimal.

So I was left with Tactical Play, Strategic Play and Endgame Theory. These provided much greater value, why?

Each of these provided tools, ideas, plans and value no matter what stage of the game I was in. Training in these areas gave me value in any position or against any opponent.

Obsess More

To make sure that I truly understood what I was learning, I needed to ensure that I had learned it deep. How did I measure that?

If I could not teach it to a class with no notes, I did not properly understand it. If I could not explain the concept without staring at several note cards, there was no way I could actually use that idea in tournament play. I would mess it up.

And so I obsessed. I had to learn it, and I had to learn it quick. I could not just learn it well. I had to learn it perfectly. I would try to learn everything I could about a particular idea before moving on. When I studied pawn play I became obsessed with learning everything about it. Doubled Pawns, Isolated Pawns, Hanging Pawns, Backward Pawns, Pawn Chains, and more. Each of these are unique concepts just about Pawns, The most basic unit in the game!

I did not stop unless I could explain the fundamentals, the most basic concepts to anybody who would ask. I did not need to have a note card with positions that would allow me to teach it. I could create the positions to demonstrate the concept and idea.

This greatly reduced the amount of time I had to spend preparing lessons. Previously, for any given lesson, I was spending roughly 30 minutes per lesson creating unique lesson plans. This lead to 15 hours a week of preparation time. By obsessing, when I would sit down to create my lesson plans, I could either skip preparation as I knew the content so well that I did not need to prep, or it would take me less than 15 minutes to create the plan and organize materials. This brought my preparation time down to roughly 6 hours a week with the combination of beginner and advanced students (more time to prep for advanced students). This freed up almost 10 hours of time a week.


It did not take long after I switched gears before I started to improve dramatically. After fully making and implementing the changes, it took me 3 months to jump ~150 points to 1808, making me a Class A player.

Additionally, my students started to do much better. My players and teams won 5 of the 6 available chess championships. Two of my students became National Masters. A couple of my students went to the World Youth Chess Championships to represent the United States of America.


I spent less time, roughly 25 hours a week less between studying and preparing lessons, but improved dramatically. Why did this work?

In his book, Great At Work, Morten T. Hansen writes extensively about the concept of working less and obsessing more. He emphasizes that focusing or narrowing down your priorities by itself is a flawed strategy.

“The term “focus” consists of two activities: choosing a few priorities, and then dedicating your efforts toward excelling at them. Many people prioritize a few items at work, but they don’t obsess - they simply do less. That’s a mistake.”

I have seen time and time again, someone reads Tim Ferris’s near cult classic work, The 4-Hour Workweek, and they try to optimize and reduce their work. They say no more, they do not work on the things that they view as low value.

But they also do not work harder on the things that matter. They do not obsess over them.

Learning how to focus on and obsess over my work has allowed me to excel in many more areas than the chess community.

In the Software Engineering program at the Milwaukee School of Engineering, there is a year long project that Juniors must complete to prepare themselves for their Senior Year and subsequently, their Senior Design Project. My project was developed using a set of technologies known as the MEAN stack.

Several of my team members struggled during the course of the year. Why was this?

They never obsessed over any part of the project. They tried to learn about everything and in turn learned only a little bit about everything. They were extremely broad scoped and not “T-Shaped” individuals that Scrum, an Agile work process, benefits from. This lead to poor results and overworked team members. Some team members logged 30-40% more hours than was required in order to reach basic goals.

To make matters worse, most of the team members had spent their first two years as developers working in Java. Despite appearing to have many similarities, Java and JavaScript/TypeScript are very different languages. Almost nobody on my team obsessed over how the language that we were developing in worked.

Nearly six months into the project, and one of my team members admitted that they did not understand how Promises, a fundamental idea to handle asynchronous operations, worked in JavaScript and had only been copying and modifying code that other team members had written in order to make their function calls work. This lead to hours of debugging problems as they were writing their code with relatively little results. When asked, they could explain what a Promise was, but not how to use them.

They had failed to obsess over the tools and fundamentals they needed in order to accomplish more complex tasks. This caused them to have to work longer to accomplish what they were working on.

Not learning Promises in JavaScript is an extreme example of where we failed. When we obsessed, we did succeed.

When attempting to handle complex parent and child communication with several components in that same application, we had a team member who obsessed about the best way to handle that communication. They researched every possible way they could find to make it the easiest implementation for the team.

The team settled on using services to handle the communication. Why? It allowed communication within the family of components rather than just bidirectional communication between parent and child. This way updates were seen across multiple components. Without that team member’s obsession, we would have had to work harder to implement more logic in the parent component to handle the communication from child to sibling children components.

How do I know we worked less due to that team member’s obsession?

Because we had failed to build that application the first time around using other methods. Our product owner and tech lead required us to do a full rewrite after our first 6 sprints worth of work on the project. That particular section of the project had taken 3 sprints with full focus from the 5 person team the first time around. It took only a single sprint and three team members the second time with the superior architecture.

At your job, what should you prioritize to obsess over?

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