May 2025

Cooperation is the evolutionary force behind families, friendships, communities, and most of civilization. Humans can work together, even with strangers, “before we can walk or talk.”

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But sometimes, it fails us.

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We’re not great at discerning when to compete instead of cooperate. And when we get it wrong—when we bring a cooperative mindset to a zero-sum game—we lose. Or worse, we get average results in a game where average is equivalent to losing.

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I think about this as a simple rule: Cooperate in positive-sum games. Compete in zero-sum games.
 

The difference is obvious in sports: one winner, one loser. Clearly when it's zero-sum (i.e. winner-take-all scenarios), you compete. But in life, the rules aren’t posted at the start of the game. We often default to cooperative behavior even when only one person can win.

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Take job hunting. It’s a high-stakes, zero-sum game—only one person gets hired. Yet most people converge on the socially-approved approach: follow the directions, polish your resume, write a heartfelt cover letter, submit your application. In doing so, they converge toward the same strategy as everyone else. And in a sea of sameness, most people sink.

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In these situations, conformity kills your odds. What works is divergence.

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When I was a broke, 22 year-old, living in a hotel in San Francisco’s Tenderloin, I didn’t apply for jobs. I started working for the job. I sent handwritten letters to my target list of companies. Every time I met someone from one of those companies, I sent them a project in advance: strategy pitches, customer analyses, memos, market deep dives. Not just once—at every step.

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I did the work that they would ask me to do on the job before they gave me the job. Eventually, the VC firm that hired me said that I was introducing a potential HR violation. I had to stop or they had to hire me. So they hired me.

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I call this the “work for the job” strategy. I outcompeted hundreds of “more qualified” candidates by refusing to play the game the socially standard way.

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This instinct to diverge—to compete where others cooperate—applies in any high-stakes, zero-sum scenario. You have to ask: is there only one (or very few) prizes? And if so, what would it look like to break the mold instead of fit it?

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Of course, most of life isn’t zero-sum. Most of the time, cooperating works, especially in relationships, family, and parenting—domains where effort compounds through collaboration. Competing here destroys trust and erodes what you’re trying to build.

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The trick is knowing which game you’re in.

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Most of us lean heavily toward cooperation. That’s usually right. But when the stakes are high and the prize is scarce, your biology might be steering you wrong.

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And in those moments, divergence is your advantage.