The lost art of losing

Jan 25, 2017 /

We’re all scrambling for practical solutions for the uncertain future of work. But there’s a mental shift we need to make, too.

We live in a winner-take-all world. As kids, we grow up competing for attention in our families, for grades and friends at school and for triumph in sports and debates. Later, as we enter the world of work, we learn how to win others over. But we must always play to win. Management literature is full of instructions for “how to win a customer,” “how to win a pitch” or “how to win in the stock market.” In business, politics and most other fields, victory is never bittersweet, and losing is always sour.

Sure, there are things like Fuckup Nights, a global spoken-word series of public confessions from startup founders and business leaders who failed, often miserably. But failing is not the same as losing. You may be able to “fail fast,” as Silicon Valley’s folklore has it, before a quick pivot — but failing is a far cry from losing, which can be agonizingly slow, with no possibility of full recovery. What has failed can be fixed; what is lost is lost. And it’s a problem. Here’s why losing is actually a lost art.

For decades, we’ve been narrowing the space in which we can lose without social stigma. Our obsession with winning has enabled a tyranny of efficiency that views what composer Claude Debussy called the “space between the notes” not as music, but as waste. A society where the only remaining art is the “art of the deal,” where the winners are the best dealmakers, and where everybody gets only what they pay for, is a failed society. In a climate that knows the price of everything but the value of nothing, we are starved of the material and spiritual resources we need to thrive.  Economic principles now invade all aspects of our lives. From a market economy, we have morphed into a market society in which business logic consumes the heart of politics and our civic fabric. We have normalized a transactional, zero-sum view of the world.

In tomorrow’s workplace, losing will become a more critical trait. Not just as a way to show and form character, but as the character of our times. Work will become a far less reliable vehicle for distributing wealth, assuring economic stability and affirming our identities. With software and robots predicted to replace up to 50 percent of the human workforce in the next two decades, we will see many jobs disappear, employment cycles shorten and the gig economy soar. In this new super-flexible workplace, we will have less status, less authority and less control over our work.

Many of us will find ourselves at an unfair disadvantage competing for maximum efficiency with ever smarter machines. Confronted with machines’ relentless mechanisms of winning, forced into becoming smart machines ourselves, the ultimate bastion of humanity may be our ability to lose. Machines simply stop functioning; they can fail, but they can never lose. Unlike the machines, we can choose to act morally, even and especially if it’s not worth it, if it’s an argument that can’t be won. Winners don’t fight for a lost cause. The rest of us should.

We need to create systems, rituals and supports that allow us to find ourselves even when we lose. These might include peer-to-peer mental health services, career transition counseling, communities like Burning Man, OuiShare or DO Lectures that sporadically assemble and offer us shelter from the paths of linear logic, and of course — more acutely than ever — the arts and humanities as access points to other lives, to hidden, foreign or lost worlds. And we will require leaders who have the humility to acknowledge that their wins are never more than Pyrrhic victories at best unless they address profound human desires or create real social equity and not just fleeting customer satisfaction or one-sided wealth.

The task for all of us will be to lose with class and dignity in order to remind us of something more worthwhile than winning. And the great opportunity ahead will be to understand losing as essential to the human condition: “I lose therefore I am.” In the Tour de France, the famous yellow jersey is awarded to the biker who is leading the race. The worst-placed rider is granted no such visible honor: people simply refer to him as carrying the “Lanterne Rouge,” a term that recalls the red lantern hanging from the rear of a train’s caboose. The writer Max Leonard wrote an entire book about the “guy at the end of the pack,” because, says Leonard, “he sees a lot more of the race and there’s a lot of rich stories there to tell.” This is a refreshing perspective — and one that more of us need to adopt.

As we concede ground to the regime of machine thinking, let’s try to look at our lives as one long, evolving concession speech. We ought not to view the professional defeat or the personal loss as just a bump on the road, but embrace the fact that losing is the very basis of our shared humanity. Every day, it becomes more obvious what we’re losing when winning is the only option: everything.