What Chess Can Teach You About Making Decisions

A couple of topics I frequently come back to are decision-making and iteration. Decision-making is central to the design of anything. An iterative process provides a roadmap to improving and shaping something over time. You might think I formed these opinions while studying design, but the truth is they came to me while learning to play chess. Sometimes you learn things in unexpected places.

The moves on the board available to a knight in the center and one in the corner
A knight in the center of the board has eight potential moves, while one next to a corner has three

I recalled my unexpected learning after reading the article Good Design is About Process, not Product, by Jared Sinclair. The article argues that process differentiates the quality of your work and that you develop a better process through good habits. It’s a good read.

Jared offers several habits of successful designers. One is to delay decisions until they need to be made. The delay allows for more exploration and keeps you from being locked into your first thoughts. While I agree with the idea, I didn’t like that the advice was listed as be indecisive.

The word indecisive carries a negative connotation about not being able to decide. It suggests more than delaying a decision so can remain open to new possibilities.

Improving your position increases the probability of your success

I started thinking about decision-making, which led me back to my chess learning days. I thought I’d share what little I learned about positional and tactical play in chess and how I apply it to the decisions I make now.

Note: Please know I’m not a great chess player. There’s a good chance I’ll get some things wrong discussing positional and tactical play. It’s ok. The reason for sharing isn’t to teach you about chess, but to show you something I learned and apply from my understanding or perhaps misunderstanding of chess.

Positional and Tactical Chess

When I first moved to Colorado I didn’t have a lot of money. I wasn’t entirely sure I was going to stay here for any length of time either. For both reasons I found myself living in the hostel here in Boulder within a few days of arriving.

People from all over the world passed through. Few of them stayed beyond a few days. The overall character of the place would change with the change of people. For a few days chess was the thing. A young man from Switzerland was taking on all challengers, defeating each and every one.

I thought I’d give it a try and see how I could do against him. It had been years since I played chess and I knew I wasn’t good so I picked up a beginner’s book in the hopes of learning something.

Among the earliest lessons was the value of different squares on the board. The ability of a given pieces increases when it can attack and defend more squares on the board. It’s a simple concept and it means the center of the board provides a stronger position than the sides, because the center offers the most possible moves to pieces that occupy it.

When you control the center of the board you hold a stronger position. You have more and better ways to attack your opponent’s pieces or position and defend your own. Consequently a poor position ties your hands and restricts what you can do with your turn without making a bad move.

With my newfound, albeit limited, knowledge about chess, I sat down for a game against Stephan (I think that was his name). I lost, though I played better than most people had against him. After the game I was even sure I had the advantage at one point, but didn’t have the tactical skills to press my advantage into victory.

The experience made me want to learn more about chess, which I did until something else came along and grabbed my attention. I’m still not a good player, but I did learn a few things such as the concepts of positional and tactical play.

Positional play is focused on longer term movements that aim to improve your position on the board. Tactical play seeks shorter term advantage, usually the capture of an opponent’s piece. Tactical chess seizes an opportunity for short-term gain. Positional chess improves your position, knowing it’ll provide more tactical opportunities at some point.

Again, I’m quite possibly getting the above wrong when it comes to playing chess, but what’s important is where my understanding led me in regards to making better decisions.

Chess as a Guide to Decision-Making

In chess and in life you’re faced with a lot of difficult choices. Sometimes there isn’t enough quality information to decide and you have to lean on your values, principles, and process to guide your decision-making.

I think the central idea that should guide you is to improve your position. For example I never worry about where I’d show up on a list of talented designers. All I care about is getting better so that tomorrow I’ll be a more skilled designer than I was yesterday. I’m concerned with improving my position.

Whatever your situation when faced with a decision, choose the path that improves your situation. Your choice doesn’t have to solve your problem or take you to the promised land. Just improve your position and you’ll find yourself a little closer to where you ultimately want to be.

If the idea sounds like iteration, that’s because it is. You iterate your position in life because a better position will provide more opportunities for success. You position yourself to be in the right place and right time to act on the opportunities that are always in front of you.

Have you ever known someone who’s luckier than everyone else? It’s not luck. That person has simply put themselves in a better position. Luck is probability. When the odds of something happening (winning the lottery for example) are very low we say someone who’s successful against those odds is lucky.

Improving your position increases the probability of your success. It’s what’s meant by making your own luck. In the case of a lottery the initial odds are stacked against you to the point where it won’t make a difference, but it will make a difference in many other things.

For example your odds of finding a job increase the larger your social network. Increasing the size and quality of your network improves your position. Luck doesn’t get you the job. A better position does.

Positional and Tactical Design Decisions

I’ve hardly talked about design and yet I feel as though I’ve been talking about design this whole time, given how important decision-making is to design.

When you gather information from clients and define the problem to solve you’re establishing a position on the board. You improve that position by developing a concept, adding constraints, and working toward unified goals.

Your concept, your solution to the problem, provide the guidelines for what is a better position. Make a decision in unity with these guidelines and you improve your position. Veer from them and you weaken your position.

The stronger your design position, the more tactical opportunities you’ll discover and the more confident you’ll be in exploring them from the solid foundation your position gives you.

Closing Thoughts

Perhaps it’s a strange place for a lesson about decision-making, but my limited understanding of chess has been influential in helping me make difficult decisions.

I no longer try to go from start to finish in a single bound. Instead I think of my current position and the choices in front of me. Most of the time I choose the option that put me in a better position. I don’t care if the increase was 100% or 0.1%. As long as the decision improves my overall situation in some small way, I have no worry in making it.

I keep an eye out from my current position to identify potential opportunities. These opportunities may temporarily distract for some gain within reach. I’m confident in my position to know I can defend it and continue improving it after exploring the opportunity.

The idea to make decisions that improve my position has served me well. I hope something in my story, experience, and observations will serve you well too.

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