12 min read

Mastering the Art of Not Winning

Mastering the Art of Not Winning

Trophies aren’t why we do things, but gosh, they feel great to win. 

Who doesn’t relish the spotlight for a moment? Feeling all eyes look on with admiration, that sense of achievement, those compliments from friends and strangers—it’s the ultimate dopamine hit. 

Those trophies validate a job well done, a great idea brought to fruition, or just sheer outworking of your competition. As much as that trophy can feel like Thor’s Hammer in our grip, its absence might be even more powerful.

All I do is win, win, win? 🎶

Let me tell you, for every award I won, there’s significantly more I have not won—likely even more than I can count. If there were an award gala that gave out trophies for not winning, I’d have a lobby that looks like Miles Brand.

Not winning is not fun. Just like eating your vegetables and doing exercise isn’t fun, not winning improves you. It forces you to evaluate your work ethic, quality of output, and attitude. When it happens, it’s up to us to turn not winning into something meaningful by finding a lesson buried in the pain and growing from it. 

I have a powerful and vivid memory of each and every non-win seared into my brain. Each left a stronger, more profound impression than most of my wins. I’ve tried to use the pain, anguish, and disappointment as fuel to win at the next opportunity. Fuel to power the next move. Voters or judges somewhere decided I wasn’t the champion. My drive to win is surpassed only by my desire to prove others wrong—fuel to show them. Fuel to be victorious.

“Losing feels worse than winning feels good.”
Vin Scully

Arguably worse than not winning, for myself, is watching someone else not win. I’ve sat across the table from colleagues who haven’t won, tears streaming down their faces. I’ve consoled friends who came in last place. I’ve seen strangers crumble when their name isn’t called. Like a gut punch with no ability to swing back, I despise this feeling.

On all these occasions, I’ve realized most words offered are utterly pointless during the moment. People say a lot of things, “You should have won,” “You’ll get them next time,” and “It’s not fair.” 

This list of trite pleasantries goes on and on. Yet none of those words really ease the sting or make sense of not winning. Often, the bystander is spouting these quips to comfort themselves in an otherwise uncomfortable moment. These thoughts and ideas I am writing about today are for everyone who hasn’t won, including myself. And for our inevitable future selves who don’t win at something.

So, I Had a Bad Day? 🎶

My earliest memory of not winning was when I was thirteen or fourteen years old as a Boy Scout. A particular award was given annually to the Scout who had the greatest impact by helping other Scouts. All the youth in the troop voted on it—all of my adolescent peers. I thought winning was a sure thing for me because I had let encouraging words fuel my ego leading up to this night. I nearly fell out of my chair when someone else’s name was called, and I did not win. 

I was mad.

I disagreed.

I cried. 

I alternated between jealousy and depression.

I thought I should give up since my hard work wasn’t acknowledged. Worse, I became consumed with reasons why the other kid shouldn’t have won. I spent far too long sulking. As T-Pain would later postulate, “Did you have a bad day, or did you have a bad five minutes that you talked about all day?”

Eventually, at my parents’ urging, I did some soul-searching. By the way, soul-searching in that phase of life is far less stoic and profound than it sounds. I think my parents were fed up with the angst-ridden teen eating all the food in the fridge out of depression. I had to step outside my self-absorbed bubble to examine the situation objectively. 

Only then, through eyes not mine, I could acknowledge and appreciate the qualities of the person who did win. The most challenging moment wasn’t just swallowing my pride and congratulating him a week later. It was accepting that he had been better and deserved to win—because he did. In the omniscient third-person version of this story, I did not want to be the enemy. Instead, in my life’s story, he gave me the gift of learning how to not win.

The Winner Takes All 🎶

I’ve shaken hands and congratulated winners, even when my opinion differed. Since that teenage lesson, I’ve made it a point to be sincere in my congratulations, even when I felt they shouldn’t have won. While my personal views may not align with the judges’, I’ve learned to keep them to myself. The old adage holds true: “If you can’t say something nice, it’s better to say nothing at all.”

Sportsmanship means being fair, ethical, and respectful to everyone you’re playing with. The greatest trick the devil ever played was convincing the world that life is a zero-sum game and that to win, someone else must suffer defeat.

“Avoid status games in your life, they make you into an angry, combative person. Politics, academia, and social status are all zero-sum games. Positive-sum games create positive people.”
Naval Ravikant, The Almanack of Naval.

In “Unreasonable Hospitality,” Will Guidara retells the evening he and his chef-partner Daniel Humm attended the World’s 50 Best Restaurants, hoping Eleven Park Madison would be ranked as one of the World’s 50 Best Restaurants. He and his business partner optimistically and egotistically guessed they’d rank at 40 or maybe 35.

"The lights went down, and the music played. The emcee for the night was a handsome, debonair Brit. There was a little preamble before the man said, “To kick it off, coming in at number 50, a new entry from New York City: Eleven Madison Park!” 

“That knocked the wind right out of us. We slumped over and stared at our feet. The night was over for us before it had even begun.”

Later in his book, he chronicles the stages of grief in painstaking detail. A forced smile and wave. A bottle of bourbon. Bargaining and depression. Self-depreciation by referring to their honor as last place, rather than celebrating 50th. Anger slipped in as they considered the ridiculousness of anything possibly being “the best in the world.” Quicker than most, their night ended with acceptance as they compared their work to the likes of five-time winner El Bulli and four-time winner Noma. They finally decided they had got what they deserved. That final epiphany would set the stage for their next era.

“We’d worked our butts off to earn a spot on that list, but what, really, had we done that was groundbreaking? The more we talked, the more it became clear: nothing."
Will Guidara, Unreasonable Hospitality.

What most people fail to understand when their name isn’t called is that they have a front-row seat to watch the winner and learn. The rhetorical questions of “Had we been groundbreaking?” “Did I deserve this award?” or “Am I worthy?” can only be answered by comparing to the declared winner. Realizing they’ve walked this path ahead of you means you have a path to follow. Follow your competitor, congratulate the champion, and befriend the winner; they have the treasure map.

Eleven Madison Park goes on to increase their rank on the “World’s Best” list seven more times, earning the #1 spot in 2017 and in seven short years, traveling from a perceived defeat to winning so hard that they are no longer eligible for the award!

For Guidara, much more came from not winning than winning. The best-selling book creating America’s preeminent hospitality symposium, The Welcome Conference, recognized by Wall Street Journal as an Innovator, being featured on an episode of Netflix’s 7 Days Out. None of which would exist had he won that night in 2010.

Pour Your Misery Down on Me 🎶

One of the greatest displays of not winning happens every year during February. Two football teams meet in the Super Bowl, American sports’ biggest and most important game. Besides Gatorade and Disneyland, a staple of the climatic end is a blanket of the winning team’s colored confetti raining down on a packed stadium. It’s a beautiful and incredible sight, at least for the victor. The winner gets everything: t-shirts, interviews, diamond rings, and ticker tape parades, except confetti. Everyone gets that. Confetti doesn’t discriminate; it falls on both teams equally.

I always look for the few dawdlers who stay on the field after the rest of the team has retreated to the locker room. Why do they subject themselves to the fanfare of their defeat? Are they replaying moments that could have changed the game in their head? Is this modern-day self-flagellation? Or are they fueling up for next year? 

I can learn from those basking in the misery of not winning. Running back to the locker room will only dull the pain. That’s where all the empty words of sympathy are being tossed around. Staying on the field, you learn to face the reality of not winning. You need to sit in your competitor’s confetti.

After my years as an adolescent Boy Scout, I returned to serve as Camp Director for the next generation of Scouts. For two years, I had the honor and privilege of managing nearly 100 camp staffers, overseeing the instruction of tens of thousands of merit badges, and keeping a watchful eye over the 1,000-acre camp. The culmination of each camper’s week was earning a coveted camp honor award by showing various ecology, swimming, leadership, and Scout Spirit attributes. 

Every Friday night, I stood on the parade ground overlooking the Ohio wilderness and spoke to the entire camp. As Camp Director, I gave a speech that had been repeated verbatim by every Camp Director since 1926. 

“To those of you who have earned your award tonight, I congratulate you. To those of you who have fallen short of your goal, I encourage you to return next and try that much harder.”

Looking out at the sea of Scouts every week, from 12 to 17 years old, I knew I was breaking someone’s heart. In that crowd was someone like me. Someone who did not win when they thought it was a guarantee.

Programs like summer camp exist to prepare young men and women for the difficulties of life. Learning resilience, humility, and courage are among the most meaningful and challenging virtues to attain in life.

I believed then, as I do now, that to reward someone not deserving can do a greater disservice than trying again. By rewarding undeserving behavior, we risk sending the wrong message and discouraging others from trying again. Recognizing and rewarding effort and merit is important, as it encourages growth and perseverance.

Gimme Three Options 🎶

As a songwriter, Taylor Swift has a record-setting seven Song of the Year Grammy nominations, tied only with Lionel Richie and Paul McCartney. However, one key difference from Lionel and Paul is that Taylor has never won. Headlines across the internet seemed to relish her inability to win, her accrual of “the most losses,” and her unfortunate “losing streak.

With that kind of not winning credit, when she recounts her journey of not winning Album of the Year for Red in 2014, I listened. It ended up that she needed that moment. And all her other un-winning moments. Watch as she so perfectly describes the three options every person can have when they don’t win:

That’s right; you have the power to decide how to react! And her three options when you don’t win an award are simple:

  1. Decide the judges voted wrong
  2. Decide the winner didn’t deserve to win
  3. Accept you might not have done award-winning work

Said out loud; options #1 and #2 sound wildly juvenile. Those are the words of a moody teenager lashing out. They are valid feelings, of course, but Swift moves past them quickly to arrive at her epiphany: “I’m the problem; it’s me.” Look at her now, her recent Eras Tour surpassed $1 billion in revenue, becoming the highest-grossing music tour in history. She was fueled by not-winning.

The Ancient Greek philosophers Epictetus and Marcus Aurelius wrote extensively about the Latin phrase “amor fati” or “love your fate.” Accept your fate rather than suffer imaginary problems in advance or pine for life’s situations to have concluded differently. If you can’t change, embrace. 

Lorraine, my density has brought me to you...

A situation might not be pleasant; it might cause deep pain or discomfort. Extreme acceptance because it is fate, taken to the point of love, removes all power from circumstances. This feeling frees us to act progressively in the future and not react defensively in the moment.

“Do not seek for things to happen the way you want them to; rather, wish that what happens happen the way it happens: then you will be happy.”

More than Words 🎶

I hope you’ve noticed I have focused on calling it not winning instead of losing. Generally, we aim to avoid losing as much as possible.

There is a distinct difference between a situation ending with less versus not gaining. Exiting a set of circumstances with a net gain of more is a win. Compared to an actual, subtracted, negative loss. Less money, less time, physical change, a demerit, or punishment. Only exiting with less is losing. It’s hard to comprehend why most people feel the absence of recognition is somehow less, but we do. We immediately verbalize it when it happens, “I lost.” It’s as if the award was a set of keys misplaced around the house. 

Maybe this is nuanced grammar; at most, I’ll call the act of “not winning” a “failure to win.” Walking out of the ballroom without a win doesn’t subtract from who you are. Maybe you did win in a way, if you consider that moment a better character-building moment than winning.

You Gotta Fail to Succeed 🎶

Often, not winning is exactly what we need. To work hard and not win is validation that it wasn’t enough. Yet, not winning has the potential to propel you into your next act. Abe Lincoln lost a lot. Defeated for Illinois state legislature and later for Speak of the Illinois House. A run for Congress in 1843 and 1848. An attempt for the US Senate in 1855. A bid as Vice President in 1856. Another try at the Senate in 1859. 

You’d think big, bold, high-profile attempts at public service would be enough to deter Lincoln. Each miss forged his tenacity and deepened his resolve that would come to define his presidency. His comfort with misfortune and defeat removed the sting of adversity from his life, allowing him to navigate challenges with resilience and grace.

“I have been too familiar with disappointments to be very much chagrined.
Abraham Lincoln, Communication to the People of Sangamo County.

Similarly, tales of not winning are common among those who eventually achieve great success. Who could forget Susan Lucci? So famously not winning a Daytime Emmy a record breaking 18 times, that her eventual win was announced by the presenter with an exuberant proclamation: “The streak is over!

Some might know what happened to Oprah at 23. After being the first black female news anchor in Nashville, she moved to Baltimore for the coveted six o’clock news anchor position. And then she was fired. Yikes! But only in hindsight does it seem appalling that someone would fire Oprah…

In her own words, nearly 40 years later, she’s the first to say, “I wasn’t a very good reporter.” And it was likely the best thing to happen to her. As Leslie Jones describes the situation, “She was just some 23-year-old punk who needed to get fired to become Oprah.”

Like a superhero or villain who needs an origin story and conflict before they can rise to the occasion, we should all be required not to win—at least once. Because sometimes, as many people like Lincoln and Oprah demonstrate, you gotta fail to succeed.

I Tried So Hard, and Got So Far. It Doesn’t Even Matter 🎶

In early 1987, Rick Rubin produced the Beastie Boys’ album “Licensed to Ill,” which topped the music charts. A first for a rap album or artist. When asked how it felt, Rubin replied, “I’ve never felt worse in my whole life.”

“All I ever want to do is make good music. I’m making something that I love that the world loves, and it did nothing for whatever was going on inside.”
Rick Rubin, The Creative Act: A Way of Being.

All that matters to Rubin is the work itself. He’s made a career fostering, supporting, and believing in artists to help them find their authentic voice and create their best work. He eschews awards, accolades, and praise. He expects nothing and often says in a zen-like tone, “The reward is in the doing.”

In 1997, Matt Damon won his first Oscar for Good Will Hunting at just 27 years old. It was an undeniably pinnacle moment for any actor, and he achieved it after less than a decade in the craft. Sitting on the sofa and looking at the award that night, he was overwhelmed with an unlikely emotion. 

“Imagine chasing that, and not getting it, and getting it finally in your 80s or your 90s with all of life behind you and realizing what an unbelievable waste of your life.”
Matt Damon, The Graham Norton Show.

Providing wisdom on the emptiness of winning from those who have won might seem ironic. It’s exactly who I want to take advice from. Celebrating is easy and quite fun. Sometimes, winning doesn’t feel that great anyway. There’s little left to learn once you’ve won.

And in the End 🎶

I’m quite proud of fifteen-year-old me. When that particular Boy Scout award came around the following year, I appreciated the traits of my competitors. They had each done tremendous work, and I was ready to congratulate any one of them. I had become apathetic to the outcome. I had found self-confidence in my work. And I was enthusiastic to be a cheerleader in someone else’s story. It was the ultimate “journey is the reward” moment.

I won that year. Or at least I think I did. It might have been the year after. It became a footnote in my life. It’s the year I didn’t win that became a chapter.

“Winning isn’t everything, but wanting to win is.”
Vince Lombardi

So I hope you win all of the things you reach for. 

But then again, it’s OK if you don’t. 

It might be the best thing for you.