Beyond the Finish Line

You can follow every rule and earn every reward.

And still feel like something's missing.

Because most of us were trained to play finite games.

Finite games have set goals, rules, and obvious winners.

→ Get the degree

→ Land the job

→ Climb the ladder

→ Secure the title

It feels productive. It feels safe. But eventually, it feels empty.

Because the goal of a finite game is to win.

But the moment you "win" the game ends. And you're left wondering…what now?

When I sold a company earlier in my career, it felt exactly like this, completing a finite game.

My immediate reaction was to jump straight back in, to chase another win, hoping the next would feel different.

But soon enough, I felt empty again.

I've learned that momentum, meaning, and mastery come from playing infinite games.

Infinite players don't play to win. They play so the game keeps going.

→ They seek progress, not perfection

→ They build for tomorrow, not just today

→ They let go of control to invite surprise

→ They build lives around causes, not careers

The key insight is you can only keep playing by being willing to change.

Choosing the infinite game isn't easy. It requires courage to walk away from common markers of success.

But the infinite mindset isn't reserved for those with abundant choices; it's what helps us create new ones.

It gives us the courage to step away from chasing degrees, fancy job titles, or society's approval.

The shift begins with a simple question:

Not "How do I succeed at work?" but "What game am I choosing to play?"

This one shift reframes everything:

→ Tasks become moves

→ Problems become puzzles

→ Careers become adventures

→ Setbacks become storylines

And suddenly, you're not just competing, you're compounding.

Today at High Output Ventures, it feels entirely different.

I partner with people who deliberately choose infinite games, people who care deeply about what they're building, not just what they're achieving.

You can quickly tell who's playing a finite game versus who sees their work as an infinite endeavor.

The conversations, relationships, and energy are fundamentally different.

This distinction matters more in the AI era.

AI can already outperform most finite players. It optimizes faster, scales effort, perfects execution.

But it can't choose a cause. It can't embrace surprise. It can't reinvent the game itself.

That's still our move, if we choose to make it.

So I'll leave you with this:

Finite players strive for control. Infinite players seek growth, even if it means losing what they control.

If your path never surprises you, it's not an infinite game, it's a script.

Winning ends the game. Playing with purpose keeps it alive.

And when you play with purpose, you don't just shape your career, you shape your mind, your relationships, and your freedom.

In the end, the only game worth playing is the one you've chosen yourself.

Are you playing someone else's game, or your own?