Playing the Game vs. Winning the Game

Hey everyone, and welcome back to The Long Run. Crazy to believe, but today is the last day of Q1 — they weren’t kidding, time really flies as you get older. This week’s post is a bit of a personal story, tied to a larger theme I’ve been thinking a lot about lately: how life is similar to a game.

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When asked to define success, Warren Buffett has said,

“Success is when the people who you want to love you, do love you.”

Whether or not we agree with Buffett, it’s worth examining how a man known for being one of the richest, yet humblest, in the world views his life’s purpose. Notice that he makes no mention of making a certain amount of money or attaining some prestigious career, but he focuses on relationships. The key variable in his success equation is the group of people you want to love you.

Whose love do we actually care about?

If we really pause to think, that group is probably much smaller than we might have originally assumed. For me, it’s probably my family, parents and grandparents, and maybe a few friends. Sure, there are a lot of people I care about beyond that small circle, but I’m not gaining much by trying to impress them.

When we splurge on things like fancy cars or luxury goods, or we aspire for prestigious jobs, are those things bringing us closer to the goal of making the people we want to love us actually do so? Or have we expanded our scope of people we want to impress to a larger group — classmates, social media followers, and others we want to show how great we are?

The smaller we keep our group of people we want to impress, the more likely our decisions are to align with actual happiness and fulfillment. We then make decisions for ourselves and the people we actually care about.

A personal backstory

For as long as I can remember, I’ve always been a competitive person. From playing cards with family to pickup basketball with friends, I took winning games seriously. At around 12 years old, I started learning about the stock market and was enamored by the idea of making money. Naturally, I decided that I wanted to work in finance and be an investor when I was older. “What better way to make money than playing a game where money is the scorecard?”

I took a lot of math and accounting classes in high school, chose a college with a strong business program, and set a goal to “work on Wall Street,” whatever that meant, and whatever it would take to get there.

In my freshman year of college, as I met older business students, I saw that the smartest, most successful ones were interning and getting job offers at investment banks. This is what I assumed the best and brightest did — and it’s what the school was designed to optimize for.

In my sophomore year, I traveled to New York City for the first time with a group of friends over spring break. We were all on the same investment banking track, and we toured the offices, networked with banker alumni, and did what we called “recruiting.”

After several days of coffee chats and hustling all over a frigid New York City, I was infatuated with the idea of the lifestyle of a New York investment banker. And as there appeared to be a hierarchy, it had to be at one of the best banks — the so-called “bulge bracket” ones, where if you work there, people will really respect you.

Working on billion dollar deals, wearing fancy suits, earning hefty bonuses, and the high-flying lifestyles they lived — it seemed like a dream life. If I could only get there, I told myself, I would have finally made it. From a small town to the top of the world — this is what I thought success looked like. If we’re being honest, I wanted to be an investment banker and rise up the ladder because I assumed other people would think more highly of me.

But the reality is no one is thinking about you. They’re thinking about themselves.

As college students looking up to these bankers, we weren’t impressed with the actual people, but we were imagining ourselves being in their shoes and other people being impressed with us.

This is similar to what Morgan Housel calls the “Man in the Car Paradox” in The Psychology of Money. The Man in the Car Paradox says that you think having a fancy car would make people like you more, but when you think about that fancy car, even you don’t think about the person in the car. Instead, you think about how having the car would make other people view you.

I did achieve the goal of getting that dream summer internship. But I learned during the internship that the job was not what it seemed from the outside — it paid well, but it was far less exciting than the vision I was sold.

Meanwhile, in my free time during college, I was spending time with startups on the side, not because I had to, but because I was genuinely interested. It didn’t feel like work. It felt like play, and I was learning stuff I actually found interesting.

At the investment bank, I was only concerned with winning the game. But working with startups, I found fulfillment through simply playing the game. Don’t get me wrong, I still wanted to win, but winning wasn’t the end in itself.

So, as you can probably predict by now, instead of returning to the bank job after graduating, I took a chance and moved to the West Coast to work at the startup. This decision was probably the hardest but most important one I’ve made in my life so far — the choice between deciding for myself versus deciding to impress others.

Before continuing, I want to emphasize that I’m not encouraging people to quit their job tomorrow and just do what they love. Dependent on a number of factors, this can often be incredibly risky and stupid. I was lucky to have a promising opportunity, and if it didn’t work out, I had a safety net of a traditional corporate job that would always be there to fall back on.

But I give this story as an example of a larger theme — internal versus external benchmarks of success.

Most of us aspire to live a life where we do things with our time and money that actually make us happy.

But in reality, many of us actually live lives where we make decisions to impress other people. We find ourselves climbing ladders we don’t actually want to be on.

Instead of optimizing for admiration of others, using our time and money to achieve independence, autonomy, freedom, and meaningful relationships with those we actually care about is far more valuable.

Everyone is living in their own world. They’re all playing their own game.

The rules of the game

The reason many people love video games is that the games establish a clear goal with rankable achievements. In Tetris, we rearrange shapes to score as many points as possible. In Fortnite, we collect resources and defeat opponents to be the last one surviving. In Mariokart, we try to win races. Get points, defeat enemies, win the game.

Video games have clearly defined boundaries, where the most skilled players typically win.

Careers are different. The metrics for success are less defined, and we have an endless number of variables interacting with each other to control the outcome. There’s also a lot of luck involved.

It’s easier to just play by the values of the game than to determine your own.

A clear example of this phenomenon is the college admissions process. Every year, the U.S. News & World Report releases its ranking of the best undergraduate colleges. This commonly accepted standard of excellence removes the idea that “best” could actually be a highly subjective measure. Every student values different things — what they want to study, geographic location, size of the school, extracurricular activities, and any number of other factors.

When someone else determines for you what it means to be successful, there is no longer a need to define it yourself.

As we navigate through our careers and decide what we should spend our time and money on, we should ask ourselves,

“Am I more interested in playing the game or just winning the game? Would I still play this game if I could win and not tell anyone about it?”

Our lives are far too short to play games we don’t actually want to win. But they’re far too long to get stuck in the wrong games.

-Owen

Fresh Finds

New Yorkers (WGGTB)

Article | 5 minutes

Really enjoyed this short piece about a New Yorker’s firsthand account of growing up and spending most of his life in the city, before moving to South Carolina. He mentions some of the pros and cons of cramming the smartest people in the world into a 17-mile island, and the stark contrast between New York and his new life.

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