Chapter 5

Infinite Game

In his quirky philosophical treatise, Finite and Infinite Games: A Vision of Life as Play and Possibility, New York University professor James Carse describes life as a game with two types of people: finite and infinite players. Finite players accept the roles life gives them (e.g., college student, manager, lawyer, parent, spouse) and play by the received rules in an effort to win. Infinite players play with the roles and bend the rules, not to win the game but for the joy of playing.

For example, rather than buy art for a collection, New York City–based art collective MSCHF purchased Damien Hirst’s painting L-Isoleucine T-Butyl Ester for $30,485, cut out its eighty-eight colored dots “so everyone can have a spot” (priced at $480 each), and then auctioned the “spotless painting with 88 holes in it” for over $250,000. This stunt is just one of many MSCHF has pulled off that break rules and challenge the game.

For finite players, uncertainty is the enemy because it creates unknowns about the ability to win. For infinite players, uncertainty is the realm of opportunity, and they play with the “expectation of being surprised!”1 As Carse argues, “To be prepared against surprise is to be trained. To be prepared for surprise is to be educated.” There are many ways to live as an infinite player.

Infinite players challenge their roles. Carse writes that we tend to identify ourselves by the roles we play in life, such as our job, relationships, or status (student, consultant, parent, etc.). But when we identify with a role, we are less likely to experiment with it because failure to “do it right” implies failure as a person. By contrast, if we view roles as temporary, changing, and separate from who we really are, then we are more free to experiment, reinvent, and transform them. For example, when a finite player loses their job or gets divorced, it crushes their identity, whereas an infinite player, after taking time to absorb the loss, views it as an invitation to reinvent their role.

Eleanor Roosevelt illustrates the reinvention of roles in the face of difficult challenges. Raised by an alcoholic father who died by suicide, then a stern grandmother who suddenly passed away from diphtheria, Eleanor recalls feeling like a displaced ugly duckling that didn’t belong. Imagine her elation when she married the jovial, charismatic star of the Harvard social scene, Franklin D. Roosevelt, and settled into her new family as wife and mother. It was only after bearing six children and while unpacking Franklin’s suitcase from his trip to Europe, she discovered love letters between him and her secretary, Lucy Mercer. Eleanor offered Franklin a divorce, but his controlling mother, whose house adjoined theirs via sliding doors, threatened to cut Franklin off from the family fortune if he did.

After a period of deep grief in which Eleanor “faced myself, my surroundings, my world, honestly for the first time,” she decided to reinvent her role.2 She started business school, learned to drive, and took cooking lessons. She fired the servants, or “spies,” hired by her mother-in-law and surrounded herself with friends, including African Americans and others deemed inappropriate in her social circle. She started working for the League of Women Voters to fight for unemployment insurance, the abolition of child labor, and wages-and-hours legislation.

Eleanor’s own political career was just taking off when Franklin came down with polio, and she put everything on hold to massage his legs, roll him in bed, and administer catheters and enemas. Despite her mother-in-law’s demand that Franklin retire from political life, Eleanor insisted he continue and traveled the country speaking on his behalf, writing a nationally syndicated newspaper column, and hosting a weekly radio show. After Franklin’s death, she both advocated for the United Nations and became America’s first delegate, helping to frame the Universal Declaration of Human Rights. When she died, the New York Times noted she was “the object of almost universal respect.”3 She could have stuck to the roles of obedient wife, rejected lover, submissive daughter-in-law, but she did not. If she had, Eleanor knew she would have become “a completely colorless echo of my husband and mother-in-law, and torn between them, I might have stayed a weak character forever.”4

Infinite players challenge the rules. Too many of us take the rules for granted without realizing they are made up. As filmmaker David Lynch describes it, “We think we understand the rules when we become adults, but what we really experience is a narrowing of the imagination.”

The most distinctive characteristic of Tesla CEO Elon Musk is his willingness to challenge the rules. “The one thing you can never do is tell Elon, ‘That’s the way things are done,’” said Sterling Anderson, former head of the Model X.5 Musk’s approach is to “boil things down to the most fundamental truths in a particular area, the things you’re really sure of are base truths, or highly sure of, and then you reason up from there.”6 For example, batteries have long been a bottleneck to affordable electric vehicles. Musk challenged the industry standard of $600 per kilowatt hour by breaking batteries down into raw components and demonstrating that the materials could be purchased on the London Metal Exchange for $80 per kilowatt hour. “Clearly, you just need to think of clever ways to take those materials and combine them into the shape of a battery cell, and you can have batteries that are much cheaper than anyone realizes.”7

Likewise, George Yancopoulos and Len Schleifer, founders of Regeneron Pharmaceuticals, observed that one reason for the exorbitant cost of developing new treatments is that so many therapies fail in the transition from animal to human testing. They challenged this bottleneck by splicing the human genome to develop a mouse that bridged the animal-human divide. This new mouse allowed them to radically improve their testing accuracy, lowering development costs by 80 percent, as compared with competitors.8 Reflecting on the origin of their remarkable breakthrough, Yancopoulos told us, “We challenge everything. Every concept. Every scientific principle. Nothing is unchallengeable and you don’t take anything for granted. Most of what we believe are facts are not.”9

Another way to challenge the rules is to rethink the way you interact with other players, even the competition. While at Cisco, Kate O’Keeffe observed that some of the most interesting and valuable opportunities happen at the boundaries between industries. She created the Cisco Hyperinnovation Living Lab, an outside-the-box forum to bring together uncommon partners like Visa, Nike, Costco, and Lowe’s to find opportunities at their intersections, including reimagining retail and supply chain.10 O’Keeffe reenvisioned the boundaries of the game, intuiting that competitors could work together to create new opportunities beyond the grasp of any individual company: “We are all each other’s customers and face common problems, so why not work together to create something more?”11

Infinite players also challenge the game itself. Zach Klein, cofounder of Vimeo, recalls learning this lesson the hard way. “In the current cult of startup, it is a perfectly reasonable idea of success to start a company just to sell it very soon after for gobs of money.”12 After Vimeo took off, Klein and his cofounders did exactly that, making a fortune. But today Klein laments, “As soon as I sold my company and I was standing safely on the ground, I wanted nothing more than to have those wings again. I just wanted to keep flying.”

Klein set out to look for others playing the game differently and came across Yvon Chouinard, founder of billion-dollar retail brand Patagonia. Chouinard, a self-described “dirtbag” climber who got his start selling rock-climbing equipment out of the back of his car, challenged the rules of business by treating his employees well, telling customers to repair their products rather than buy more, and donating 10 percent of profits or 1 percent of sales, whichever is greater, to grassroots change and sustainability efforts. As Chouinard summarized his approach in his inspiring manifesto, Let My People Go Surfing, “I learned at a young age that it’s better to invent your own game, then you can always be the winner.”13

All of us, due to living within a cultural setting, are handed a set of metrics by which we are told we should live—a game and a set of rules. One of the things that expats often come to realize when living between two cultures is that these rules are largely made up. Recognizing that you can choose the rules you live by can be incredibly liberating. As legendary innovator Steve Jobs famously said, “Everything around you that you call life was made up by people that were no smarter than you, and you can change it, you can influence it…. Once you learn that, you’ll never be the same again.”14

What makes a startup disruptive is its willingness to challenge the rules. Airbnb challenged the idea that people would only rent rooms from a hotel, Wise (formerly TransferWise) challenged the assumption that currency could only be exchanged by big banks, and Uber challenged the idea that only taxi drivers can give rides. Imagine for a moment how amazing it would be if companies, more generally, could be even more inventive in challenging the game, and thereby create better outcomes regarding sustainability, employee well-being, and humanity as a whole.

Infinite players play for the sake of continuing the game and for discovering new surprises. One of the things that characterizes a Kaospilot student is their more holistic view of the game. “None of them would work eighty hours a week and do what they are told to earn $5 million a year…. They look for something different,” says head of school Christer Windeløv-Lidzélius. “They believe they can create something better than that. It’s OK to have more than one goal, more than one dimension of success. Our students learn to work with moving objectives and multiple objectives, and they are rarely happy if they achieve just one!”15

Most importantly, infinite players are ready for uncertainty. David Hornik, a leading Silicon Valley venture capitalist who ranks on the Midas List of the world’s top investors, struggles with dyslexia. “Because I’m dyslexic, I always have uncertainty,” he says. “The world doesn’t make sense the way it does for everyone else.”16 Hornik learned to play the game differently while attending Harvard Law School. “Going to law school as a dyslexic was a dramatically stupid thing to do,” he told us, laughing. “If I had to read everything, I was dead.”

Instead, he says, “my goal in year one was to understand the game so I could play it my own way.” For example, rather than cram for an exam by forcing himself to read, he prewrote an essay based on the professor’s interest in philosopher John Rawls. His roommate chided him, “You are insane. You have just wasted so much time. You should be studying and instead you’ve written a useless essay.” But when the professor handed out the exam—a paper on Rawls—Hornik simply handed in his prewritten essay. “I have to understand the system, because if I have to play by your rules I lose, but if I can play by my rules, I can do anything.” Hornik went on to earn high marks and become editor of the Harvard Law Review.

Infinite games might seem risky or counterintuitive to many, but Karen Arnold’s fourteen-year study of valedictorians reminds us that “college grades aren’t any more predictive of subsequent life success than rolling dice.” Why? “School has very clear rules … but life doesn’t. Life is messy.”17 So challenge your roles, the rules, even the games you are playing, and create a life of continued play and new possibilities.

Reflection and Practice

To start applying the infinite player reframe, pick one professional or personal “game” you currently are playing and ask yourself:

  1. What have I assumed is essential about this role that is actually made up or nonessential? When CEO adviser Saj-nicole Joni helps top leaders develop breakthrough thinking, she starts by asking them questions about why they see the world the way they do. But she also encourages freewriting to reframe what things could look like. To help Nathan imagine what he really wanted from his career that balances academic and practitioner research, Joni advised him to be playful in his freewrites: “What if you made this easier and more fun? What if you broke all the ‘rules’—[be] concise, precise, [use] vision, [be] forward-thinking, [focus on] challenges, etc.—and made it fun for yourself, like jamming, then stepped back and asked if there were critical things you left out—noticing, not judging?”18 The nature of finding a more infinite way to play requires a playful stance—a not-taking-yourself-too-seriously lens—which can be hard but increases with practice.
  2. How can I play with the game? Infinite players play for love of the game, more than for external rewards or outcomes. Donald Winnicott, one of the most influential psychologists of this century, talked about play being essential to healthy development and creative living. He argued that play should be something that continues into adult life, and as an old man he used to ride his bicycle to work downhill with both hands and feet on the handlebars.

    Winnicott also spoke about “transitional objects,” such as a beloved teddy bear, that help kids make the shift from earlier to later phases of childhood. Upon learning of Winnicott’s fun-loving nature, Nathan wondered if we could find a “reverse” transitional object to introduce more fun and creativity back into our overserious lives. He bought a whimsical bicycle with old-school handlebars and pedals that brake when you push backward, like the bikes he learned to ride on; now Nathan can’t help smiling every time he walks toward his bike. We also bought matching wool jackets to sew old national park patches and other cool felt patches onto, both to bring out a playful element in our relationship and to add to our curious collection of matching clothing items for when we want to go “twin,” the word we give to wearing the matching pajamas, shoes, shirts—and now coats—we own.

  3. What are the rules for this game? What ways could I challenge them? Tim Ferriss is a controversial figure because he challenges rules and boundaries. Sometimes what he does is contentious, like how he won the national kickboxing title by leveraging a rule that disqualifies participants who step outside the ring, but sometimes he identifies rules worth breaking. For example, he challenges the idea that everyone must work eight hours per day to be effective. He also asks if there are ways you could compress your work, or work in different ways or locations, to allow yourself to develop other things you want to pursue. You can ask similar questions in your life.
  4. What are the boundaries of the games I am playing? Like Kate O’Keeffe challenging the idea that big corporations can’t work together, can you challenge limiting beliefs in how or with whom you play? For example, can you find ways to make your work pay twice? Consider that SXSW, the world-famous creativity festival, emerged from an effort by musicians and creatives in Austin, Texas, to get global exposure for their work, which turned into a craft-supporting source of income.
  5. What is the purpose of the game I am playing? If you interrogate the things you believe about your life, could you come up with a more infinite game view? What would it look like to play instead of work? What would it look like to play the game just to play, versus trying foremost to win? What would it look like to see work as a chance to help others? What would it look like to add a new game? After Zach Klein sold Vimeo, he and friends went and built wood cabins, just because they wanted to. Their first cabins were poorly made, but they got better, and their efforts led to the “cabin porn” movement. That led to another effort, DIY.org, where people can upload videos to teach and share their projects, like building a tree house.
  6. How can I find and play an infinite role in difficult games? There is no doubt that life forces us into games that take us by surprise or that we wouldn’t choose to play. We aren’t trying to discount how hard these things are, but it is helpful if you can envision the infinite path. When our oldest child came out as transgender, we had a hard time navigating our complex emotions, all the conflicting advice, and our own conservative upbringing. When we asked, “What is the infinite game role for parents?” we immediately knew that “unconditional love” was the guiding star to base our decisions on. This more infinite role created immediate calm and new possibilities for healing and trust.
  7. How much effort will be required to challenge the game? In one of the most influential models of change, sociologist Kurt Lewin describes the process in terms of unfreezing, making the change, and then refreezing. Unfreezing takes immense effort because you have to convince yourself it needs to change and then get others on board before you can even start the often uncomfortable and time-consuming unfreezing phase. The change phase can feel awkward until it becomes more familiar. And finally, freezing the new changes takes time. Challenging any finite role, rule, or game is hard and requires sustaining yourself while you wait for the change to refreeze.
  8. How do I tap into the joy of playing even when I don’t win? Watch Gabe Polsky’s documentary In Search of Greatness for a motivational tour de force in the arena of athletic genius. While celebrating sports legends, the film continually reminds us that the beauty and entertainment of sport is so much more enduring than who won. “If the outcome is always to be number 1 no matter the sacrifice … what’s the point? We aren’t robots. We are people driven by feelings and inspiration and a sense of possibility. Creativity is the essence, not an inconsequential aspect of humanity.”19
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