What winning at the highest levels taught me, and what I had to lose before I questioned the game.

I spent the first half of my life trying to win. James Carse’s Finite and Infinite Games eventually gave me a way to understand what I had been doing. In a finite game, players compete to win within agreed rules and boundaries. An infinite game is played to keep the play going. Its rules can evolve; new players can join. Once I grasped that difference, I started seeing it everywhere, including in the parts of my own life I had been least willing to examine.

Carse put the difference in a single line I return to often: “Finite players play within boundaries; infinite players play with boundaries.” 

I came to Carse after decades as a committed finite player. I was good at the game, and I loved parts of it. This is not a story about how achievement is bad. It’s about what happens when the scoreboard becomes the purpose and you forget to ask whether the game itself is worth playing.

The game I was good at

My first career was in finance. I built firms, worked with extraordinary teams and helped take businesses public. I learned how institutions work, how incentives drive behavior, and how hard it is to keep good judgment under pressure. I am grateful for the opportunities. But I was also running a private game alongside the public one: trying to earn belonging by being indispensable.

There was always a next quarter, a next raise, a next transaction, a next number to beat. You could win on Friday and be behind again on Monday. The scoreboard never stopped. Worse, it could tell you how you were performing without ever telling you whether the life you were building was yours.

That chapter ended badly in ways I couldn’t have imagined when I began. My marriage ended, my business eventually failed, and years of legal battles accompanied that tough period. For a long time I brought the same drive to defending what remained that I had brought to building it. It took me years to understand that even winning those fights would not answer the bigger question.

How the scoreboard bends behavior

I know the pressure of the scoreboard from the inside. It does not require bad people to produce bad decisions. Most of us are responding to the rules and trying to do what we are rewarded for doing.

Research on financial executives has found that many will trade away long-term value rather than miss a near-term earnings target. I wasn’t surprised. If your compensation, status and credibility all rise or fall on this quarter’s number, the temptation to optimize the number becomes enormous. The behavior can be rational within the rules and destructive to the larger enterprise.

This is the territory of Goodhart’s law: once a measure becomes a target, it stops being a clean measure of the thing you cared about. Earnings can become more important than the long-term health of a company. Test scores can become more important than learning. And in my own life, achievement became more important than asking what I actually wanted.

The same logic runs everywhere: test scores in schools, engagement metrics in social media, citation counts in science. Each starts as a window onto something real. Each, once optimized, becomes a game of its own.

The rules we inherited

For fifty years the dominant script for business was simple. In September 1970 Milton Friedman published an essay in The New York Times Magazine arguing that the social responsibility of business is to increase its profits.  That doctrine shaped boardrooms, business schools and law for half a century.

In 2019 the Business Roundtable adopted a broader statement of corporate purpose, naming customers, employees, suppliers and communities alongside shareholders. I welcome the shift, but changing the statement isn’t the same as changing the incentives. A company can advertise an infinite purpose and still run every decision through a very finite scoreboard.

What infinite play looks like in practice

Carse wasn’t writing a management handbook, and I don’t want to turn him into one. But his distinction has changed how I lead and how I try to live. I still care about results. I just want the results to serve a game that is worth continuing.

Play to keep the game going. A finite player asks how to win this round. An infinite player asks how to make sure there is a next round worth playing: a customer who returns, a team that grows, a market that is healthier for your having been in it.

Hold the scoreboard lightly. Measures are indispensable. Targets are sometimes necessary. But the moment a number becomes the purpose, it starts to lie. The discipline is to keep asking what the number was supposed to tell you.

Treat people as players, not positions. Carse observes that finite games assign roles, and that players can forget they chose to play.  In a company, this is the difference between an org chart and a team. In a community, it is the difference between members and participants.

Welcome new players. The most interesting things I am building now include a Burning Man camp, gatherings of makers and artists, and With., a company devoted to human creativity. All of them become more valuable when more people can genuinely participate. Their purpose is not to close the circle around a winner. It is to expand what people can make together.

The game I am playing now

I still play finite games. With. needs customers and revenue. Bisous needs a budget and people who do what they say they will do. A deadline is real. A loss hurts. The difference is that I now want those smaller games held inside something larger: connection, creation and contribution.

I used to believe I could get to the  meaningful life once I had won the next round. I know how seductive that thought can be. Today I am trying to reverse it. First decide what kind of life is worth living. Then choose the games that serve it.

I still catch myself reaching for the scoreboard. The difference is that now I notice. And I can ask whether this particular win is worth what it costs.

Notes

1. James P. Carse’s Finite and Infinite Games (1986) distinguishes playing to win from playing so that play may continue. It is the philosophical foundation of this essay, though not a ready-made business playbook.
2. Carse’s distinction between playing within boundaries and playing with them is also discussed in Derek Sivers’ reading notes.
3. John Graham, Campbell Harvey and Shiva Rajgopal studied how executives manage financial reporting, including choices that can sacrifice long-term value to meet short-term targets.
4. Their related NBER working paper gives more detail on executive incentives and earnings management.
5. Charles Goodhart’s work and Marilyn Strathern’s later writing on performance measurement help explain why metrics become distorted when turned into targets.
6. Milton Friedman’s 1970 essay made a forceful case for shareholder profit as the social responsibility of business. It is an important reference point for the shareholder-purpose debate.
7. The Business Roundtable’s 2019 statement expanded its stated corporate purpose to include several stakeholder groups; whether those commitments changed actual behavior remains contested.