Work as a Game: Play as Both Finite and Infinite

“A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.” — James Carse, Finite and Infinite Games

The Experimental Hire

My first job was a corporate experiment. My company was hiring fresh college graduates to inject “new blood” into their support staff—a department traditionally filled with industry veterans, many doing their best to avoid whatever responsibility they could until retirement. I was part of a cohort, bright-eyed and eager to prove myself.

In many ways, the experiment succeeded. We brought energy, fresh perspectives, and a willingness to question established practices. But in other critical ways, it failed spectacularly. What the leadership hadn’t considered was the psychological impact of placing enthusiastic newcomers into a team where many viewed their roles as dead-end jobs. The veterans, many burned out or disillusioned, had created an ecosystem of cynicism that threatened to swallow our youthful optimism whole.

I found myself at a crossroads early in my career. I could:

1. Maintain my enthusiasm despite the surrounding pessimism
2. Try to “save” my fellow young colleagues from the creeping cynicism
3. Focus solely on saving myself
4. Surrender and join the ranks of the disenchanted

I cycled through all these options—enthusiasm that gradually eroded, failed rescue missions for colleagues, self-preservation tactics, and brief but brutal periods where I succumbed to the collective pessimism.

Deciding to Change Games

What ultimately saved me was a stark realization framed as a choice: I could either continue hating my work while suppressing my authentic self, or I could risk being fired by bringing my full self to work. This trade-off, this mental calculation of risk versus reward, activated something deeply familiar—the thousands of hours I’d spent immersed in games throughout my life.

Little by little, I created personal goals and started “discovering the rules” of my workplace, as I put it then. I began approaching my job with the same strategic thinking I applied to complex strategy games. I tested boundaries, identified patterns, and looked for “power-ups” and “achievement unlocks” in the form of new skills or relationships.

Years later, when I learned about my neurodivergence, this approach made perfect sense. Gamification has a well-documented positive impact on attention for many neurodivergent people. That gravitational pull toward game-like structures wasn’t just a coping mechanism—it was my brain finding an optimal way to engage with my environment.

What Makes Work a Game?

There’s a thoughtful exploration of gaming philosophy by C. Thi Nguyen that resonates deeply with my approach: gaming as an act of agency. In games, we voluntarily adopt artificial limitations and goals, creating a space where our agency can be expressed through strategic choices within defined parameters.

My first work-game was simply to learn the game itself:

• Discover the unwritten rules
• Test their boundaries systematically
• Define “progress” markers

My early metrics for progress were predictable: first money, then title, and eventually, experiences. But these were all finite games—played with the purpose of “winning” through defined achievements.

From Finite to Infinite

Later in my career, I encountered James Carse’s work on finite and infinite games. While I wasn’t particularly captivated by the entire book, the core concept profoundly shifted my thinking. I had been playing relatively small games with concrete endpoints, but what if my career could be an infinite game—played not to win, but to ensure continuing play?

This perspective transformed my career philosophy. I maintained my game theory but expanded its scope:

• I’m playing an infinite game across my entire career
• Each company I work for has a discoverable set of (often unwritten) rules
• These companies also have changing landscapes that can be mapped
• When the unwritten rules don’t align with the evolving landscape, I can thrive by finding ways to rewrite the rules
• If an organization values rigid rules over adapting to the landscape, I’ll likely struggle, as I’m naturally drawn to solve challenges even when they require breaking conventions

Moments of finite play will remain throughout the workday. Giving a great talk, landing a new concept, influencing a particular stakeholder. These moments are finite and I feel like I either win or lose in some part of my mind. But these are means, not ends. The game I care most about is the infinite one linking all these moments together.

My Career Game Chronicles

Looking back, each professional chapter has been its own game with unique parameters:

First Job Game: Understand why people buy obviously flawed technology

• Achievement unlocked: Learning to see beyond technical limitations to business value

Engineering Game: How does this technology actually get built?

• Achievement unlocked: Technical comprehension and credibility

Marketing Game: Who’s buying our products and why?

• Achievement unlocked: Customer empathy and market insights

Startup Game: Can I help build something better from scratch?

• Achievement unlocked: Innovation mindset and comfort with ambiguity

Social Impact Game: Can software creation align with social good?

• Achievement unlocked: Purpose-driven work in open source

Enterprise Open Source Game: Learning why and how open source works at scale

• Achievement unlocked: Understanding collaborative innovation ecosystems

Humane Leadership Game: Can I lead a startup the way I believe it should be done?

• Achievement unlocked: Building a remote-first, humane team culture

Recovery Game: Can I work while healing from burnout?

• Achievement unlocked: Self-awareness and sustainable work practices

Leadership Renewal Game: Can my healed self find joy in leading again?

• Achievement unlocked: Resilience and renewed purpose

Current Game: Can I effectively apply the unique knowledge I’ve accumulated?

• In progress: Synthesizing diverse experiences into meaningful impact

The Infinite Career Game

What I’ve come to understand is that viewing work as a game—particularly an infinite one—isn’t about trivializing it. It’s about reclaiming agency in environments that often feel designed to strip it away. It’s about finding the space between rigid compliance and reckless rebellion where meaningful contribution and personal growth can coexist.

The beauty of the infinite game perspective is that there’s no final “win state”—only continued play, continued learning, and continued evolution. Bad managers, toxic cultures, and dead-end jobs become merely challenging levels rather than career-ending obstacles.

When I face a new work situation now, I don’t immediately ask “What do they want from me?” Instead, I ask:

• What are the written and unwritten rules here?
• How is the landscape changing around us?
• Where is the misalignment between rules and reality?
• What game am I uniquely equipped to play in this context?

This approach has transformed my relationship with work from one of compliance to one of creative engagement. It’s allowed me to navigate difficult environments with curiosity rather than frustration, and to find fulfillment in unexpected places.

Perhaps most importantly, it’s given me permission to play—to bring the same strategic thinking, creativity, and joy to my professional life that I bring to other areas I value. The greatest surprise for me is the serious impact I can make when I’m not taking myself too seriously.

It’s all a game I am choosing to play.

What game are you playing at work? And is it finite or infinite?