Play Chess Here: Finding Your Own Path

7 min readAug 11, 2020

Last year on vacation I was driving in New Mexico on my way to the Bisti Badlands. Bisti, if you’re unfamiliar, is one of the most surreal natural landscapes I’ve ever seen. At times it felt like I was on an alien planet. The colors of the earth, the rock formations, and the lack of trails and people made it feel like a magical place. As I pulled up to the parking lot after many miles of gravel roads, I noticed a camper parked nearby with a cardboard sign in front that said: “Play chess here”. I thought that was interesting and as I got out of my car I walked over to the camper. As I approached the other side of the camper, I found a man eating a donut and sitting by a table with a chessboard set up. I told him I was going to hike and wasn’t sure what time I’d be back, but when I came back I wanted to play a game. He smiled and said, “Take your time.” When I came back from hiking about two hours later, sure enough, he was still there with the board. He told me his name was Chuck and from then on we played in silence. I noticed that he had a stack of books on the table representing three different languages — the most conspicuous one being a Louis L’amour novel. That’s interesting, I thought. The game progressed and Chuck beat me with relative ease. He shook my hand as I got up to leave and then I drove away.

As I was traversing the gravel road back to civilization, I began to think about what had just occurred. Who sits in the middle of nowhere with a sign that says “Play chess here”? That thought led me down a wormhole. If someone really wanted to play chess, there were many smarter ways to do it. For one, the internet solves this problem instantly. Even if you wanted to play in person, a city could solve this pretty well too. Chuck was using a very interesting filter. Who drives to this remote alien landscape, knows how to play chess, and then decides to play chess? That’s a lot of conditionals against the odds being favorable. I wondered whether Chuck had played anyone else the day that I challenged him to a game, or when the last time someone actually played against him. There was no timescale for my guesses. It could’ve been days, or weeks, or god knows how long. As I contemplated deeper into who this mysterious man was, I came to the conclusion that Chuck was playing his own game on his own terms. Regardless of the amount of time between games, he was content to play it. Chuck telling me to take my time while I was hiking was probably the only time in my life someone had said that to me and actually meant it. As I was making my way back home and still thinking about that day, I realized that the level of patience and calm that Chuck had, as well as his intention to play the game on his own terms, are probably two of the most underrated superpowers in our modern world.


“Most people overestimate what they can do in one year and underestimate what they can do in ten years.” — Bill Gates

We live in an era of short-termism, fear of missing out, and impatience. As more companies compete for our attention and to be the gatekeeper for our dopamine release, it becomes increasingly easy to fall into a trap of mindless action. The moments of creativity, deep thought, or reflection fade increasingly far apart — punctuated more and more by the sound, vibration, or visual notification that someone or something is pulling us away from what we were trying to do. We fight this battle constantly — desperately trying to stay conscious in choosing how our days get spent. If we’re not careful, weeks, months, or years can go by as we get trapped in these loops. Many of these stimuli serve only to make us more impatient. Long term goals fall to the wayside as our nervous system arousal has us in a frantic “putting out fires” mode for longer portions of the day. Studies are now showing that many become frustrated within 30 seconds of waiting for their tv or computer to stream a video. Don’t get me wrong, technology is great, as is the convenience it has brought to our lives. The expectation of convenience, however, is not so great. This expectation permeates more and more of our waking life. It’s why so much of the self help section isn’t just about making changes, it’s about making changes fast. Get rich quick. Lose thirty pounds in thirty days. Long games are for suckers. If only that were the case.

It’s no better at the organizational level either. Corporations focus obsessively on the next quarter. They pull out all the bells and whistles to juice the short term metrics, even at the expense of the more distant future. Government, especially recently, has also mimicked this corporate behavior when it comes to fiscal responsibility. High time preferences have become the law of the land. For some, mortgaging the future feels like the only way to compete.

In stark contrast to this trend, there is the classic example of patience: Warren Buffett. As Buffett’s mentor Benjamin Graham instilled in him, “In the short-run, the market is a voting machine, but in the long-run, the market is a weighing machine.” More generally, patience is the ability to parse between signal and noise. The short term produces a lot of noise that, taken in the aggregate, can produce a clear signal. But on its own this noise can lead to a path of randomness. Patience is succeeding at finding the signal, having a vision, and the conviction to deal with an uncertain future. Now more than ever, there is an asymmetry for those focused on the long game. Your time horizon dictates your fate.

Playing Your Own Game

“If you do not change direction, you may end up where you are heading”― Siddhārtha Gautama

We each have our own timeline that is uniquely ours. At instances in our lives, it may converge with a company that we work for or a university that we’re attending, but the aggregate of that timeline is yours, and yours alone. It’s all too easy to forget this. Alas, there’s a paradox here, for even though it’s yours, you don’t get to pick the end point (unless you commit suicide). So how do we spend it? What are our terms for this time? If you don’t have terms, then your terms will default to the forces around you. We often look at history and come across people who did stupid or terrible things and think, “I would never do that.” But as the study of humans and systems progress, we see that most of us are capable of a much broader spectrum of ethical decisions than we could imagine. Being in the wrong environment can foster undesirable results. Through time, we may look back to the beginning of our journey only to realize with horror how far off the path we’ve strayed once we are violently ripped off of it. But that’s just it, you can’t know you are straying from the path if you don’t even have a rough idea which path is yours. Therein lies the danger.

Coming up with your own path so that you can play your own game isn’t easy. We can rationalize not doing it our whole life by justifying how busy we are on the present task — the irony being that the task cannot be that important if the bigger picture is rudderless. Finding our own path can be painful, too. It may mean making changes to our lives in the present that may feel uncomfortable at first. But the struggle to find our own game means that once we identify it, we can actually start playing it. Your game has your own rules, including boundaries of ethics, discipline, balance, etc. If people don’t fit in your game, you don’t have to play with them. This becomes an even more virtuous loop when you combine it with patience.

As I think about these principles now, I flash back to Chuck. Am I playing my own game? Do I have the patience to wait for the right opportunities to play that game? Only time will tell. The rules of each person’s game may change over the course of one’s life. Refinement will be necessary as we evolve. Patience may shift as well. As we age, our affinity for patience may increase for some aspects of our lives, but for other things an immediacy will grow that we never valued before. It’s not about perfection or having it all mapped out with certainty. The game just has to be your own and needs to be reflected upon from time to time. And if you ever see a guy in the middle of nowhere with a sign that says “Play Chess Here,” make sure you play a game!