How Game Theory, Poker, and Catan Rewired the Way I Think About Business and Relationships

How Game Theory, Poker, and Catan Rewired the Way I Think About Business and Relationships

Built From the Field by Chris Momongan

🗓️ Posted: May 3, 2025

✍️ Category: Strategy & Mindset

I didn’t study game theory in a classroom. I absorbed it around card tables and late-night Catan sessions. Somewhere in between bluffing in poker and trading sheep for brick, I realized: these games were teaching me how to think, how to lead, and how to move through business and life with intention.

♠️ Poker: Pressure Reveals Priorities

Poker introduced me to the idea of Game Theory Optimal—a way of playing that can’t be exploited, no matter what your opponent does.

But what stuck with me even more was the concept of polarized betting—when you bet big with either a monster hand or a total bluff. The goal? Force the other player to make a tough decision under pressure.

I’ve used that same principle outside of poker—whether it’s in deal negotiations, setting rental rates, or making a counteroffer that pushes the other side to move. The pressure forces clarity. It surfaces what people really value.

You don’t always win the hand. But you learn the table.

🎲 Catan: Playing the People, Not the Game

Catan taught me that strategy isn’t just about resources—it’s about relationships. The board doesn’t win or lose the game. People do.

Sometimes the most influential player isn’t the one with the most points, but the one who understands the emotional landscape—who knows when to make someone feel seen, when to yield, and when to strike.

Business works the same way. Deals don’t always go to the highest bidder. They go to the person who understands the real motivation on the other side of the table.

💵 Monopoly: Control, Even Back Then

Even as a kid, I didn’t like leaving outcomes to chance. I was brokering trades and forming silent alliances in Monopoly before I knew the word “strategy.”

That hunger for control—finding a way to bend the game in my favor—was my first lesson in game theory. And it came with a shadow.

🧠 When Strategy Gets Too Calculated

I remember reading The 48 Laws of Power in college. One line stayed with me:

“Never outshine the master.”

I understood the wisdom in it. I even used it instinctively at times—around bosses, mentors, even friends. But it left me feeling... hollow. Like I was performing all the time. Calculating. Managing how I was perceived instead of just being me.

Could I still play smart without playing small? Could I be strategic and still be real?

💬 What Changed When I Met Myredith

Everything shifted when I met Myredith. At 27, I had just walked away from a job I hated, ended a long-term relationship, and was sitting in the wreckage of what felt like an identity crisis. But with her, I didn’t feel like I had to win anything.

For the first time, I didn’t need a persona. I could be vulnerable. Messy. Honest.

And that honesty—her acceptance—became the most stabilizing force in my life. It taught me something strategy never could:

Sometimes the most powerful move isn’t a bluff. It’s showing your hand.

🎯 Playing the Long Game

I still believe in strategy. In reading the room. In making intentional moves.

But now, I pair that with self-awareness and clarity of motive. Before I make a move, I ask:

  • Is this rooted in confidence or insecurity?
  • Am I trying to connect—or control?
  • Would I be proud of this play 10 years from now?

🔁 Final Takeaway

Strategy might get you ahead. But integrity is what keeps you there.

Game theory sharpened my thinking. But life—and love—taught me when to drop the act.

In the long game, the real win is showing up fully and still making powerful moves—no bluff required.

🔗 Keep Following the Journey

More real-time reflections like this, straight from the field.

Instagram @chrismomongan

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