How to Lose Like a Winner

How to Lose Like a Winner

By Sean Braswell


Because losing is an art, and one that we could all stand to master.

By Sean Braswell

Vince Lombardi has been dead for almost half a century, but the oversize mark he left on American sports remains, and not just on the Super Bowl championship trophy that bears his name. In many ways, the former head coach of the Green Bay Packers championship football teams of the 1960s is, as Sally Jenkins of The Washington Post once noted, “still alive, haunting NFL locker rooms in photographs and sayings on the walls, a fedora covering his square-cut bristles, blunt teeth bared in a grin-grimace, shouting epigrams.”

Lombardi’s best-known rousing one-liner, “Winning isn’t everything; it’s the only thing,” is also where the iconic motivator punches through the wall of the locker room and grabs at the collar of American culture more broadly. Before Charlie Sheen, before Donald Trump, Americans had anointed Lombardi as the high priest of the nation’s true national religion: not football, not Christianity, but winning. To be sure, Lombardi was not the first to invoke the sentiment (UCLA coaching legend Red Sanders used a version in the 1950s), and indeed he regretted doing so. “I wish I’d never said the thing,” he would later lament.

Still, a powerful meme was born, one that was not just catchy and compelling but that, as new research and thinking across a range of disciplines suggests, was also largely wrong and (rather ironically) self-defeating, even in the dog-eat-dog world of professional football. And, contra Lombardi and the #Winning world that has succeeded him, it’s becoming clear, as another generation of psychologists, management thinkers, entrepreneurs, athletes and trainers are discovering, that what we should be focusing on, paying homage to — even plastering to the insides of our boardrooms and locker rooms — is the power of losing.

If you want to succeed in life, business or sports, then you first have to learn how to fail, fail a lot and fail well.

The Downside of Winning

“America will start winning again like never before,” President Trump promised in his inaugural address, a recurring theme of his campaign and a bumper-sticker slogan that resonated with a good portion of the country. As Lombardi himself observed, “It is and always has been an American zeal to be first in anything we do, and to win, and to win and to win.” And while America is not alone in its obsession with winning, it has certainly made an effort to be first, even if, as my colleague Eugene Robinson points out, we don’t tend to valorize the actual winners — whether it’s the despised dynasties of the New York Yankees or the New England Patriots or undefeated individuals like Floyd Mayweather Jr. — as much as the concept of winning itself.  

Trump winning

During his inaugural address, President Trump promised, “America will start winning again like never before.”

Source John Moore/Getty

Aside from our feelings toward some winners, winning itself tends to feel pretty good. But it is not always a good thing for you. For one thing, success can be quite misleading as an indicator of an individual, team or company’s underlying merit. Bill Gross, a serial entrepreneur and the founder of the business incubator Idealab, recently conducted a study of hundreds of startup companies that found, somewhat contrary to his own company’s name, that what really drove success more than the originality of an idea, a good team or a quality business plan was timing — which accounted for 42 percent of the difference between success and failure. 

If we had won the World Series … I could have been a complete jackass.

Former Boston Red Sox pitcher Calvin Schiraldi

Winning can also make you complacent, either by giving you a false sense of your abilities and blinding you to your shortcomings, and, once you become content, even arrogant, you stop learning as much or working as hard. Business history, among other things, is littered with the corpses of complacent companies who grew too comfortable and were ultimately beaten by scrappy upstarts. Case in point: Research in Motion (RIM), whose ubiquitous, even iconic, Blackberry dominated the market for mobile communications until it was blindsided by the iPhone and the Android operating system. The same complacency hazard lurks in sports. We don’t all win four national championships in seven years, but what Alabama’s head football coach, Nick Saban, told USA Today last year about how he battles that condition should be a daily affirmation for us all to repeat: “Complacency creates a blatant disregard for doing the right things or continuing to do the things that you’ve always done to help you be successful.”


And you don’t have to be successful to be complacent or blind; sometimes just having an unrealistically positive attitude is enough. You shouldn’t forget what you’ve read about “the power of positive thinking,” but you should view it with a healthy skepticism, just like so much else in life. According to some psychological research, being happy and having an optimistic outlook may have some benefits, but if you are relying on them to bring you attainment and success, then you may be visualizing up the wrong tree. One study found that moderately happy people were more successful in terms of income, education and political participation than very happy people.

Losing Isn’t Everything, But It’s Everywhere

The good news is that failure, unlike precious metals, is common and valuable. Failure often doesn’t tend to make the headlines unless it’s a Bill Buckner–esque choke or a Google Glass flop or a Cleveland-long championship drought, but it’s everywhere, including behind the success stories of so-called winners. A tap-dancing act once defeated Bob Dylan’s high school band in a talent competition. “I missed more than 9,000 shots in my career, and 26 times I was trusted to take the game-winning shot and missed,” no less than basketball legend Michael Jordan once pointed out. “I’ve failed over and over and over again in my life. And that is why I succeed.”

Failure should be viewed as an event, not an identity, points out Jimmy Page, the mid-Atlantic vice president of field ministry for the Fellowship of Christian Athletes and the author of best-selling motivational books like True Competitor. And it’s an event that can be used to improve. “Those with a winner’s mindset use a loss to get better. Defeats don’t crush them,” says Page. “A loss just leads to another opportunity to win.”

Michael Jordan crying

While not a complete failure, Michael Jordan once noted, “I’ve failed over and over and over again in my life. And that is why I succeed.”

Source Andrew D. Bernstein/Getty

We’ve all heard the truism that losing builds character, but more importantly, it builds knowledge and motivation. There is no trial and error without error — and lots of it. And mistakes, it turns out, are really a form of a wake-up call, even at the molecular level. When we make a mistake, our brain homes in quickly on the source of the problem and raises our attention level when it comes to the next decision so that we do not repeat it. Neuroscientists have discovered that this wake-up call can happen extremely fast in the brain, sometimes even before we are consciously aware of the error. This is one powerful mechanism hard-wired into us (but not utilized) that explains why mistakes can be so conducive to learning.

It also explains in part why choosing to embrace your failures and learn from them can be such a constructive route to winning. This sort of acceptance applies not just to garden-variety mistakes but to devastating losses as well. Former Boston Red Sox pitcher Calvin Schiraldi is probably best remembered for being the losing pitcher in the famous Game 6 of the 1986 World Series, where he was one strike away from giving the Red Sox their first World Series title since 1918. After retiring, as Curt Menefee and Michael Arkush chronicle in their new book, Losing Isn’t Everything, Schiraldi returned to his hometown of Austin, Texas, and had a rewarding career as a coach at St. Michael’s Catholic Academy, something he wouldn’t change for the world, including victory in Game 6 and a World Series ring. “I think I’ve affected a lot more people this way,” Schiraldi reflects, “than if we had won the World Series. I could have been a complete jackass.”

Learning to Fail Better

Just because failure is everywhere and it’s valuable doesn’t mean it has to be rewarded in its own right. One of the more bizarre contradictions of American culture is that even as we valorize winning, we tend to reward losing as well, most notably in the form of the now ubiquitous participation trophies (a $3 billion-a-year industry!) handed out like candy in junior sports leagues. That sends the rather unmotivating message that success is really about just showing up. While mistakes can send a wake-up call to your brain, if we are not careful about acknowledging failure, negative feedback can also lead the brain to shut down, to ignore the mistake to avoid feeling bad. Research by a psychology professor at Stanford, Carol Dweck, has shown that an excess of praise and recognition in children can lead to underachievement and an inability to cope with challenges and adversity, which can cause problems in college, the workplace and later life. “A win today might be to just ‘show up’ for your training session, even though you absolutely don’t want to work,” as Page puts it.

Big trophy small trophy

Even if you aren’t the winner (right), finalist (left) and participation trophies have become part of a healthy business.

Source Jean Catuffe/Getty

Page’s point is backed up by neuroscience, including research into the neurotransmitter dopamine, the so-called “reward molecule.” Dopamine receptors play a key role in forming both good and bad habits, but through your own attitude and behavior, you have the power to boost your own performance, perseverance and outlook by learning to associate task completion with feeling good — essentially administering a hit of dopamine to yourself that will boost your confidence further and lead to behavioral reinforcement. Kind of like a neurochemical participation trophy that rewards actual achievement and only costs the effort involved.

Despite our abundant experience of failure, there is still so much we do not know about it. Hence, learning more about failure is a big opportunity, Leticia Gasca, the executive director of the Failure Institute, which researches cases of startup failure, tells OZY. “There’s next to no open data about [failure], and most of what there is is not reliable.” Gasca’s LinkedIn bio lists some of her career failures, and she considers thinking about failure as just being realistic. If you look at the data, she says, when it comes to entrepreneurs’ first or second attempts at starting a business, they’re more likely to fail than succeed. “If you know that it is a possibility, you’re going to face it in a better way.”

The topic of failure, however, remains rather taboo among entrepreneurs, athletes and people in general, but the good news, according to Gasca, is that many millennials, raised in the wake of financial crisis, are more open to confronting their fears and failures. Still, studying failure and learning its many lessons remains, as Gasca puts it, “a blue ocean of knowledge” awaiting a new generation of intrepid explorers. 

So, time to fire up those dopamine receptors, ignore the motivational Lombardi quotes along the walls and march out boldly today. And don’t come back until you’ve tasted — and appreciated — the sweet fruits of defeat.