The Lost Art of Losing 




I find it difficult to pass up the occasional viewing of Major League when its on TV. Bob Uecker on the calls, Jack Daniels infused candor. Classic. On this note, I just checked the box scores from the NHL and the NFL. Both my teams in their respective leagues are dead last in the standings. In a strange way I’m ok with it. Makes me love ‘em more. Especially when they’re in the tank. There’s something to be said for having nothing to lose. Freedom to swing for the cheap seats without a rational care in the world.

Any sports fan would love to see their team in first place all the time but obviously this isn’t realistic, even for franchises with payrolls large enough to fund a small government. I’m not here to criticize billionaire owners or endorse any kind of Moneyball concept to offset the advantage of deep pockets. This is a deeper dive into the societal norms taking root in the way we act as people on any playing field, not just athletes or competitors. With the heightened focus placed upon “winning” and “losing” as the sole benchmark of success, we live in an expanding culture of “everybody should get a prize” in attempts to level the playing field for all. Everybody should win!! Everybody should own a bigger house, a new car, and a million-dollar image, to compare notes with others, keeping up with the Jones’. All without the trappings of responsibility that accompany foolish and unsustainable needs we place upon ourselves and those around us. Bullshit!! We need some tough love.


Do you remember your last tough loss?

Did you document it?  

What did you learn from it?

What do you do differently as a result?

Who have you shared it with?

Do you still view it as a "loss" now? 


Many of us don’t often get to these questions. We’re usually stuck in our own world of judgement and comparison. This is where all learning typically ceases. We simply don’t grow the awareness to identify our blind spots and broaden our focus when needed. We live in a world of “What do you do?”, “How much do you make?” and “How good are you?”, forfeiting the examination of game changing evidence that fuels larger growth and development.

 It’s nice to be able to claim victory, rewards, and praise but we all know these are only the by-products of success, not the source. We’ve all encountered and been “sore losers”, less than gracious in defeat. This is understandable in certain circumstances. We’re human. Obviously, it’s not uncommon to see this at times but what has changed is a growing shortage of gracious winners. Some don’t even seem happy in victory. Their actions or lack thereof, cross the line of cockiness or overconfidence into an overwhelming fear of failure that grows within them once they’ve lost their center. Is this success?

 Examples of this are in every direction and hit much closer to home in the form of human behavior. Many of us are willing participants in pop culture. We glamorize it. It’s become part of our accepted ecosystem. Kids look up to professional athletes who are paid ridiculous sums to perpetuate an outdated mode of thinking that leads franchises away from the seeds of a real, meaningful, and lasting definition of success. Some politicians claim moral high ground on issues they themselves have never experienced and then bawl like an evangelist once they’re caught leveraging their privileged position for personal gain. But it’s standard procedure and likely to continue, in the name of winning, and doing so at all costs. If a top paid athlete chooses to take performance enhancing drugs to “play the game” and multiply their next contract, that’s on them. They will be exposed and shamed eventually. AFTER they take their guaranteed $100 million dollars and retire to a tropical location in the sun. Wall Street bankers have run institutions into the ground and exited with massive compensation packages while taxpayers pick up the tab. We’ve all seen this movie before. But over time, it seeps into other parts of societal areas, occupations, and mindsets. Like it or not, we’re all drinking the kool aid in one way, shape or form. We fall victim to the images of success, winning, and the rewards it provides us on our own front. Hollow though it may feel at times, it pays us what we are led to pursue. What’s more, it’s become almost taboo to lose, even if we’ve given our finest effort. It’s as though we could have and should have done “whatever it takes” to win the game, close the deal, and cash the check. No matter what. Nothing personal, it’s just business.

 To be fair, success can mean wildly different things to different people, as it should. THIS is the point I wish to impart here. What if you were willing to lose, in search of a true vocation that best suits you rather than compromising your identity to simply chase a bigger payday? As someone who tends toward indifference in difficult situations, I now recognize my character flaw for what it is: an opportunity to leverage this version of apathy productively. Staying in the moment, detached from results, allowing me to let that which does not matter, truly slide. I refer to this as, “playing for free”. Staying true to my initial intentions, free of unnecessary noise and distraction, getting paid on multiple fronts, beyond just money.

I’m convinced the most abrasive personalities wrapped up in what they call success, are not confidently bold, but fearfully recognizing how the system has manipulated them into someone they no longer recognize when they look in the mirror. This is perfectly illustrated by much of the macho, alpha bullshit we see in movies. In reality, a loss or two is good for any individual, team, or movement in its ability to temper ego-based motivations. It’s meaningful perspective that allows us to return to more of who we really are, rather than who we think we should be. What if you ran your own race and just enjoyed the hell out of it first? An experimental side hustle completely divorced from results, pure love of any game you choose. Then focused on finding the intersection between self-fulfillment and the secondary benefits it could provide others. A bit idealistic I’m aware, but I’m not after a “reasonable” theme here.

 At what point are we compelled to reject this notion of always winning and realize there is a time for everything? Maybe a loss is in the cards on the latest venture. So what? Lighten up Francis. It’ll wake us all up to the freedom of larger pursuits that transcend money, image, and material reward. All it could take is a loss or two to provide a little perspective. Perhaps we’ll find greater avenues of fulfillment and success BEING who we truly are rather than DOING what gets us paid the most, free of the superficial approval we crave from the outside world. If you already love who you are and what you do, more power to you. You are an example to the rest of us. I would venture to say you likely pursued what you love to do based upon who you are FIRST, and the paychecks followed. In more ways than you can count….      


-Buddy Kane





Posted by Buddy Kane on


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Wow, this is a powerful post. Time to read it again.

Posted by Tim Bray on Friday, December 10th, 2021 at 2:16pm

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