Leverage Maps #4: Play the Right Game, Win on Your Terms

I'm not that good at chess. I can hold my own for a while given a game with clear rules, equal information, and win conditions. But I'll eventually get outpaced by someone who lives for structure, memorization, or optimization. But I'll thrive given a game with fuzzy rules, incomplete information, and layers of social, technical, and strategic complexity.

That realization changed how I work, what I build, and how I choose where to invest my energy.



It's easy to think that comparative advantage is about skill. But it’s not just about being better. It’s about being better in the right environment.

The twist? Most people never stop to ask what kind of environment brings out their best.

There are people who shine in structured, rule-based settings where the rules are fixed and the winner is whoever plays most efficiently. Think accounting or operations roles. That’s not my environment. I do fine, but I don’t come alive there.

Instead, I hit my stride in systems where the rules are flexible and success requires you to navigate ambiguity. I do best when I choose to compete in the types of games where pattern recognition, synthesis, and strategic timing matter more than perfect play.



Here’s how I started mapping that out for myself:

  • I feel boxed in while in roles that required rigid precision and step-by-step execution
  • I find clarity that others couldn't in the type of ambiguous situations that are common at early-stage projects, cross-functional messes, and shifting requirements
  • I finish creative projects that most don't complete but do not always move fast

This reflection helped me realize that my advantage isn’t visible in traditional comparisons. It emerges when the system itself is evolving.



If you feel stuck or behind, ask yourself: Am I losing because I’m bad or because I picked the wrong arena?

Try this to map your own edge:

  1. Think of 3 moments where you felt unusually effective and where things just clicked.
  2. Now recall three moments where success felt like dragging a boulder uphill.
  3. Ask yourself about the environment for each:
  • Was the goal fixed or fuzzy?
  • Was the path linear or adaptive?
  • Was your value immediately visible, or did it emerge later?

Patterns will start to show. And with them, a deeper understanding of where you belong.



We’re taught to improve our tactics, but sometimes the real move is to switch the game entirely by choosing the right game, terrain, and leverage. When you do so, effort compounds faster, friction drops, and the path forward sharpens. Choose wisely.

I hope you are having a lovely time today. What environment and game do you do best in?