Is it time to quit the Great Online Game?

That’s a key mental shift. The cost of failure is as close to zero as it’s ever been, and it will continue to fall. That’s true for entrepreneurship, and it’s even more true for the Great Online Game. Because entrepreneurs are trying to build a business; when you start to play the Great Online Game, you’re just building optionality.

Even though the game only cost a quarter (back then), we may have lost sight of the fact that we were playing a game. Today, while we may no longer be scrounging around in sofa cushions looking for quarters to play an arcade game, many of us are approaching our lives with this same mentality. We really believe so much in our lives is final. This pr

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One of the biggest challenges people have when embarking on an unconventional path is disconnecting from extrinsic markers of success and listening to internal motivational cues. On the default path, you can spend an entire career playing other people’s games. At first, people on a pathless path try to fill the lack of extrinsic goals with new ones... See more

To find happiness in your career and life, embrace the philosophy of playing infinite games, where the goal is to keep playing rather than reach an end goal.

Early on in my journey, I realized that my entire goal was to stay on the pathless path indefinitely. This is what author James Carse calls the “infinite game”: “A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.”⁠2 By working backward, I realized that the biggest risks for me are spending m

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