Playing to win won't make you happier. This mindset shift will.
True success doesn't come from playing to win. It comes from finding out how to keep playing.
Phil Rosen
Issue #13
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April 25, 2022
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Reading time:
5 mins
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Welcome back to Tip Jar. There’s a misconception that playing to win is the only way to compete in life. But for the most successful people, life isn’t about winning.
Let’s get started.
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The most important game of your life
It’s tempting to get caught up in big milestones like an award or promotion. They feel good, and usually means someone else is recognizing a job well done.
But over-emphasizing these events can threaten to distract you from what writer Simon Sinek calls the Infinite Game.
In his book by the same name, Sinek provides a simple framework for why the most successful people can do so much.
He describes life as a combination of smaller games mixed into a larger, ongoing game.
There are two kinds of people, he writes. There are those who play to win short-term rewards, and there are those who play the long game to notch incremental gains.
“It is important to celebrate our victories, but we cannot linger on them,” Sinek writes. “For the Infinite Game is still going and there is still much work to be done.”
The game, for successful people, is never ending. But that allows them to leverage a long-term vision to dictate daily goals and habits.
These people prioritize how to amplify progress, rather than one-time breakthroughs.
People who play finite games look for shortcuts, he explains. They’re more likely to undermine other players because any consequences will be as short-lived as the game itself.
That doesn’t mean they can’t be ambitious, smart, or wealthy. But they operate with a mindset that’s harder to sustain over time.
Simply put, a finite game is played for the purpose of winning, while an infinite game is played for the purpose of continuing the game for as long as possible.
Shifting into the Infinite Game
There’s no choice but to be all-in in life — we can’t take anything with us once we leave. So it’s natural for people to want to play the infinite game, but it’s easier said than done.
Bad habits and short-term goals can pull us off the path of the Infinite Game, which leaves many people feeling unfulfilled. Temporary goals result in perpetual unhappiness.
Embracing life as an infinite game, however, can ease the gravity of our short-term goals. Progress, instead, becomes what we latch onto.
As I’ve written before, progress — not achievements or milestones — is our best bet for lasting fulfillment and happiness.
To pivot into the Infinite Game, ask yourself about your vision, and remind yourself that there is no finish line.
Establish the reason behind what you want to accomplish in life, and then tailor your daily habits so they are geared toward your ‘why.’
Learn skills and lock down habits that will take care of you down the line, so you can do what you want to do, for as long as possible.
Remember, the Infinite Game isn’t something you can win. It’s about maintaining an upward trajectory, without getting too caught up in snags or springboards along the way.
And it’s the tiny, daily successes — not your banner achievements — that will allow you to keep playing the game for as long as possible.
— Phil
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Tip Jar Recs
Something foreign: The greatest traveler and most prolific hiker you've never heard of. (AFAR)
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Something encouraging: This book sunk to the bottom of the ocean with the Titanic, and its replacement was bombed in a war. Now someone's could attempt a third print. (BBC)
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