The Power of Playing Your Own Game

Telluride, Colorado

When I was a kid, our family spent most of our free time playing games, and especially board games—Risk, Monopoly, you name it, we played all the classics. As newer games like Settlers of Catan came along, we adopted those, too.

Buried in the bottom of our game cabinet was a board game called "LIFE," which apparently was created way back in 1860. It quickly became the "US's first popular parlour game," which launched the Milton Bradly Company—still one of the most famous game makers in the world. In our game cabinet, we had a newer version of the game created in 1960 by Hasbro.

The board game depicted a stereotypical 1950s family trying to navigate the game of "life" in modern America. As you played the game, you would do things like try to get promotions at work so you could buy a car. Once you bought a car, you'd move it around the game board until you could find a wife to put in the passenger seat of the car. As you continued around the track on the board, you'd try to earn more money and get more promotions to buy a house (and then a better house), and you'd slowly fill the car's back seat with three kids. Or, you'd go broke, and apparently, in the 1950s, if that happened, your wife would just leave and go find someone else who wasn't such a fucking deadbeat. (Or so my recollection of the game goes. When I remember playing with my siblings, we were a bit too young to get all the rules down correctly.)

For those of us who grew up playing this game, it seemed to inculcate the idea that life is one big game, and in it, there are winners and losers. The winners are the ones who acquired the most money, the best car, the biggest house, and the prettiest wife, children, and dog. The losers couldn't buy a car, couldn't get a wife, couldn't buy a house (or lived in a small house), couldn't have kids, couldn't earn promotions, and then went broke.

The irony is that even though this was a board game, it was a very accurate depiction of 1950s values, which for some reason are still the classic values that the so-called "American Dream" is built upon today. Even though the younger generations question and break these social norms more and more with every passing decade, capitalism still dictates the financial success or failure of every person within the system, whether or not they think capitalism is a good or ethical system. The population at large still drinks the cool aid from the cult of home ownership even though the price gap between renting and buying is the largest it's been since the year 2000. (Source)

As it turns out, the idea that there's only one road through the game of life is FALSE.

As I've written about before, even straight out of high school, I was disillusioned with the standard American Dream and the typical road through the game of life. I was fixated on carving my own path in a countercultural way to serve my own agenda. Thus my young adult years began with an astutely brilliant observation and goal before I ended up succumbing to many of the typical stops on the standard American Dream: a college education, getting married way too young, buying a house—you name it. 

It took me an embarrassingly long time to figure out in more detail what my own path through this maze of American life would be, or at least what the first steps would be (I'm still figuring it all out).

It also took me an embarrassingly long time to realize that while yes, I could carve my own path, that many other people had already carved their own unique paths through life. In fact, the truth is:

Everyone Is Playing Their Own Game

Durango, Colorado

Instead of thinking about all the people milling around on this planet as competitors in the same game of life, all trying to achieve the same thing and beat out the other person for financial and sexual success, it's more accurate to think of each person as playing their own individual game, with their own unique set of rules.

Instead of assuming that you know what game someone is playing or ought to be playing, it's a good idea to take a step back and consider: what game is this person actually playing? What does "success" mean to them—what does winning the game look like? Maybe they're trying to achieve something that you have no clue about, and their apparent "failure," in whatever context you might be analyzing, is actually "winning" in the game that they're playing... but you aren't.

This framework is instantly useful in helping shed much of the condemnation or criticism that people often level against each other. Much criticism arises from one person condemning another's choices, even though the person being criticized is playing a different game entirely. (If this all seems too theoretical, stick with me—we'll get to some concrete examples soon.)

The Power of Knowing What Game YOU Are Playing

Durango, Colorado

Even though each person could be playing their own game and there are infinite variations of games to be played in life, the reality is that a few major games tend to dominate the lives of the majority of people, with the most obvious example being the American game of life detailed in the introduction. The more people that are playing the same game, the more frequently the values connected to that game are repeated and exalted, and the more frequently other people decide to join and play the same game, too.

The danger is that if you aren't extremely clear on what game you're trying to play, you can quickly get sucked into playing someone else's game—which doesn't fit you or serve you at all. In many ways, this is the struggle that I was fighting through in my early adult life, even though I didn't have the right words to explain it then. I forayed into adulthood with a determination to play my own game, yet I got sucked into many years of playing other games like religion, home ownership, college education, and more.

It's easy to get waylayed and taken off course by the popular games because so many people share those same values and parrot the same ideas. Distraction and confusion are the dangers here. If you're not ultra clear on what game you're trying to play and what your priorities are, it's so easy to begin thinking that a different game is the RIGHT game, even though it doesn't serve you at all.

Common Examples (and Counterexamples) of Popular Games

Durango, Colorado

So what is a game that you can play in life? Up until now, this has all been quite theoretical, but once you start identifying the game(s) that you're playing, it gets concrete in a hurry.

First and foremost, note that you can be playing multiple games themself, and for an introspective person who's honest with themself, many games can exist in harmony.

Outside 365 is a classic example of one type of game. The rules of the Outside 365 game are to go outside and cover one human-powered mile every single day, without fail. In order to achieve this goal, you often have to make difficult choices that preclude other games. If you value adventuring every single day, that might mean NOT pushing your body hard in the kind of massive one-day challenges that are en vogue in the outdoor adventure world today. If you try to push yourself to run the Badwater 135 as your ultimate challenge, you put yourself at serious risk of injury that could quickly derail your ability to go outside and adventure on a daily basis. So you need to ask yourself what game you're playing: are you playing the "135-mile-ultra" game, or are you playing the "run 10-20 miles every day" game? Perhaps with the right training, these two games can coexist, but maybe they can't.

In the rest of life, we see all kinds of classic games and then their countercultural examples. The businessman slaving away day in and day out to climb the corporate ladder is the 1950s example of a classic game, while the starving artist pursuing their art is the countercultural example. (However, I'd argue that being an artist and pursuing your "passion" is so hip these days that the true countercultural example might be somebody working an entry-level or mid-range job who doesn't give a shit about their career and is just trying to make enough money to enjoy the rest of what they're doing in life.)

So many people are still playing the "buy a house, have 2.5 kids, and live in the same town for the next 20 years" game. But as more Millenials and Gen Z question that status quo, you'll encounter many people playing an entirely different game, which could include renting a comfortable place (but at a much lower cost than buying a house), not having kids, and using the money and time freedom they've gained to travel the world. Even if they're only taking 1-3 big international trips per year, it's still a radically different game to play with your one and only life.

Other games include consumerism versus minimalism. Acquisition and debt versus financial independence. Consuming junk food versus clean eating. Instant gratification versus delayed gratification. Virtual reality versus the grit of the real world. Religion versus agnosticism. Groupthink versus individualism. The list goes on and on. 

The list is endless.

Endless Opportunity

Aspen, Colorado

The endlessness of the list of possible games is precisely what makes this mental framework fascinating. While the limitlessness could induce a sense of overwhelm, leading some people to default to the standard game of LIFE, for others, it creates a sense of endless opportunity.

If we slowly become self-aware enough to identify a game that we're playing that no longer serves us (or maybe never did), the infinite possibility means that even though we might not yet know what other game we want to play, we can still have confidence that a better game is undoubtedly out there, just waiting to be discovered. The thrill of discovery, the actualization that comes from self-reflection and working to live every more in alignment with your values—these things open up a world of opportunity and beauty.

Perhaps self-reflection, discovery of the unknown, and trying new things are themselves games that I choose to play that other people don't play. Realizing that many people aren't playing a game that values self-reflection is enlightening.But at the risk of stating the obvious: while there's an infinite number of games to be played, not all games are created equal.

There are plenty shitty games out there. Living well comes down to identifying what games are worth spending your finite existence playing, and then playing those to the exclusion of all others.

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How to Win Multiple Games on Different Time Horizons (and Why 5-Year Goals Are Bullshit)

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"What about when you get sick?" Responding to the Most Common Objection to Outside 365