Low diatribe

I remember hundreds of hours spent playing Monopoly growing up, and nearly as many hours fighting about it. The game was supposed to end when one player accumulated everything and everyone else lost everything. It usually ended when the first player to lose it all took revenge against the system by flipping the board. Even as a kid, something about this felt wrong. Not the board flipping — that seemed like the only rational response to a rigged system — but the underlying premise that fun required systematic elimination of everyone else.

I'll admit to owning several collector's editions now — Dr. Who and Nintendo, to be specific — but I don't play them. There's something fundamentally troubling about a system where winning requires making everyone else lose. Victory through eradication never sat right with me.

What I learned later makes the game even more insidious. Monopoly was based on The Landlord's Game, created by Elizabeth Magie in 1904 as an educational tool. She designed it to demonstrate the destructive effects of land monopolies and promote economic theories that valued productive work over rent extraction.

Magie's original game had two rule sets. The first showed how monopolistic thinking creates artificial scarcity and eliminates players. The second demonstrated a cooperative alternative where shared prosperity replaced zero-sum competition. Players could see both outcomes and choose which system they preferred.

When Charles Darrow adapted the game and sold it to Parker Brothers in 1935, they kept only the monopolistic version. Magie's cooperative rules disappeared entirely.

The irony is perfect: a game designed to show why monopolies are destructive became the most popular celebration of monopolistic thinking in American culture. We stripped away the lesson and kept only the competition.

Regular readers will know how much of a fan of Simon Sinek I am. Start With Why put words to my intuitive understanding of how the world works best, and The Infinite Game both expanded and coalesced the concepts I'd been struggling with and gave them voice. The market system should reward long-term value creation, sustainable growth, and stakeholder benefit. But the structures we've built discourage infinite thinking and reward end-game moves.

Quarterly earnings calls become the Monopoly board. The goal shifts from building lasting value to extracting maximum short-term profit. Leaders who think in decades get punished by markets that think in quarters. Companies that invest in people, infrastructure, or community building get penalized by analysts who see only costs, not investments.

We've created Elizabeth Magie's nightmare: a system that rewards monopolistic thinking while forgetting why that's destructive.

The finite game trap

I've watched this play out in organizations where I've worked. The pressure to hit quarterly numbers creates a cascade of finite thinking. Cut training budgets, delay infrastructure investments, optimize for metrics that increase shareholder value but weaken the foundation for long-term success.

The most damaging part isn't the individual decisions but how finite thinking becomes the default mode. Teams start optimizing for what gets measured in the next review cycle rather than what creates lasting value. Innovation gets deprioritized because it's risky and takes time to pay off. Relationships become transactions because trust-building doesn't show up on this quarter's P&L.

I've been that leader who understood infinite game principles but felt trapped by finite game constraints. I knew that investing in people, building trust, and creating sustainable systems would pay dividends over years. But I was evaluated on what happened in the next 90 days. The system punished exactly the thinking it needed most.

Playing infinite games within finite constraints

The challenge isn't choosing between infinite and finite thinking but learning to play infinite games within finite systems. This requires a different kind of strategic thinking.

I think about James T. Kirk, famous for being the first Starfleet cadet to "beat" the Kobayashi Maru. The scenario was designed to be unwinnable — a test of character under impossible circumstances. Kirk's solution was elegant in its audacity: he reprogrammed the simulation. When the game is rigged, the only way to win is to change the rules.

My favorite leaders do exactly this. They don't accept the premise that short-term and long-term thinking are mutually exclusive. They find ways to rewrite the rules of engagement.

I've found that these leaders develop what I call "nested game awareness." They understand they're playing multiple games simultaneously: the quarterly performance game, the annual growth game, the multi-year market position game, and the decades-long reputation and relationship game. They make moves that serve multiple time horizons.

This might mean hitting quarterly targets while also investing in capabilities that won't pay off for years. It means building relationships that create options for future collaboration, even when there's no immediate business case. It means making decisions that preserve trust and reputation, even when shortcuts are available.

What this looks like in practice

As a kid, skating was simple. Go fast. Don't fall. Win the race around the rink. Every lap had a finish line and every tumble felt like failure. I skated to prove something — speed, balance, control.

Decades later, standing in a pair of rental skates that felt foreign and heavy, I realized the race was long over. Nobody was timing me. Nobody cared how clean my turns were. The only opponent left was my own expectation that I should still "have it."

The first few laps were humbling. My body remembered the rhythm, but not the reflexes. I kept trying to muscle through the wobbles — finite thinking in motion. Every slip felt like losing. Every fall made me want to correct faster, master sooner, prove I could still dominate a game no one else was playing.

It took a few bruises before I caught the deeper lesson: skating wasn't about winning at all. It was about continuity. You don't "win" at skating. You stay upright long enough to find the flow again. You keep moving, adjust your weight, rediscover balance with each glide. You fall, you laugh, you get back up. The only way to lose is to stop.

That's infinite thinking: learning to value the movement itself more than the metrics that measure it. This is what it looks like in finite systems — making choices that serve multiple time horizons simultaneously. Not compromising on values while still delivering results. Building trust and capability even while navigating short-term pressures.

The compound effect

I've learned that infinite game thinking creates compound advantages that eventually show up in finite game metrics. Teams with high trust move faster when speed matters. Organizations with strong cultures attract better talent. Companies with sustainable practices become more resilient when markets shift.

The leaders who consistently outperform aren't the ones who optimize purely for short-term results. They're the ones who build systems and relationships that create sustainable competitive advantages. They understand that the best way to win finite games is to play infinite games.

This requires patience, discipline, and the courage to make decisions that might not pay off immediately. It means resisting the Monopoly mindset that says winning requires making others lose. It means building systems where everyone can succeed.

Elizabeth Magie's original game was designed to show that cooperation creates more value than competition. Her lesson got lost when we stripped away the cooperative rules and kept only the competitive ones. I keep thinking about what would happen if we dusted off those old Monopoly boards and played by Magie's original rules — starting with the monopolistic version to see how quickly it creates inequality, then voting to implement the Single Tax rules and watching the game transform into something entirely different.

We don't need a board game to make this choice. Every day, leaders face the same decision Magie built into her design: do we play by rules that require others to lose for us to win, or do we choose systems that create shared prosperity? The winning-ist leaders don't just play infinite games in finite systems — they gradually transform those systems to reward infinite thinking. After all, the goal shouldn't be to bankrupt everyone else. It's to build something that lasts.