Be Fearless in Victory & Defeat


February 25, 2026


Every week, I sit down to reflect on the events of the week before, extract their lessons, and gameplan how to apply those lessons toward greatness and growth. It’s a system that has always worked for me, it can work for you too. Welcome to The 199!

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Be Fearless in Victory & Defeat

I’ve been fortunate to see a lot of high level championship sports up close these last few weeks. First it was Super Bowl LX back home in the Bay Area, then it was the Winter Olympics in Milan. Watching elite athletes compete at the highest level is a joy. It’s also a learning experience, because the whole process is an exercise in managing highs and lows, triumphs and tragedies. Everyone has worked incredibly hard in pursuit of the same goal, and while someone is going to win gold, or a ring, someone else–a lot of someones–are not.

The margin between the ecstasy of victory and the agony of defeat can be as thin as the edge of a skate blade, and if there’s one thing I learned over the course of my career, it’s that there is a big lesson to be taken from whichever side of that edge you fall on in the biggest games or moments in your life. One that can set you up for future success if you allow yourself to see it and then apply it.

The only thing you have to manage is fear, in its various forms, getting in your way. Fear is always the biggest enemy of learning and growth, whether you’re the victor or the defeated.

Now, with a little bit of distance from these games, it feels like the perfect opportunity to talk about what you can learn.

REFLECTION

There aren’t many things in this world that can produce both the best day of your life and the worst day of your life, but the Super Bowl is one of them.

You’ve done all this work, you’ve survived a grueling five-month gauntlet of practices and games, scorching heat and freezing cold, you’ve bounced back from losses and played through injuries, all for a shot at immortality and the right to call yourselves champions…

…or not.

Each of the seven Super Bowls wins I was a part of produced an incredible swirl of positive emotions. The bus rides back to the hotel after these wins were rolling vibes machines. The positive energy was unmatched. We’d done what we set out to do. We’d reached the mountaintop.

My three losses were also uniquely powerful, but the range of emotion was narrower: somewhere between wanting to puke and wanting to cry. Sitting on the bus after each loss, we were crushed and stunned. It was like Andy Dufresne in The Shawshank Redemption, sitting in the back of that bus after being wrongly convicted, staring into the void, thinking to himself: What just happened? We did everything that was asked of us. How could this be?

But once the victory parties were done or the pity parties were over, what we were left with as a team was the reality of our circumstances going into the next season.

When we won, it was the understanding that this is what it’s going to take to get back here next year. This is the level. This is where we need to get to, at minimum. This is the championship standard.

When we lost, it was the understanding that this is who we were…and it wasn’t good enough. There was no hiding from it, because it said so right there on the scoreboard. That’s what you learn from failure. The losses, especially in championship games like the Super Bowl, always reveal where you must begin to improve when the preparations for next season start. This is the litmus test.

Both of these lessons can be incredibly daunting, and sometimes a little deflating, because they mean the same thing: you have a lot of work ahead of you.


LESSON

There’s a famous Haitian proverb about the enduring nature of struggle against the inevitable obstacles that show up in life. Beyond mountains, more mountains.

Now think about the Seahawks, or the figure skater Alysa Liu, or the US men’s hockey team. They just scratched and clawed their way to the mountaintop, and what do they see in front of them? For the Seakhaws, it’s next season. For Liu, it’s the World Championships in Prague next month. Another mountain. This one steeper than the one they just climbed because they’ve got a huge bullseye on their backs now. They’re going to get everyone’s best. Everyone’s elite focus. Everyone’s ultimate competitive drive. Whatever it took them to reach the mountaintop this year in terms of focus, execution, toughness and good fortune—that is their new starting point.

Then there’s the myth of Sisyphus. He pushes the boulder up the hill, inch by inch, and just as he gets to the top of the hill, it rolls back down and he has to start all over again with nothing to show for his effort.

Now think about the Patriots, or figure skater Ilia Malinin, or Canada hockey. They almost got to the mountaintop, but they slipped (literally, in Malinin’s case) and the metaphorical rock they’d been pushing up the hill got away from them. Now they’re back at the bottom and have to do it all over again next season, or for the next four years. But not before they take a hard look in the mirror and figure out what changes and improvements they need to make (however big or small) in order to get all the way to the top next time.

It’s not hard to imagine being in either position—at the very top or the very bottom—looking at the task in front of you, and saying “again!?” It’s a natural reaction, especially considering how depleted you are right at the end of the season or a major competition. And the reality is, everyone has something to work on. The winners, just as much as the losers in many cases. Because while you’re never as bad as you think you are when you lose, you’re never as good as you think you are when you win.

See, when we lose, we often go through our failures with a fine-tooth comb. We’re hard on ourselves, unforgiving. And yet, when we win, we can forgive a lot. It’s easy to gloss over the details when you have a ring on your finger or a medal around your neck. The great ones never do this, of course. They tell themselves the truth about their performance at all times, at all costs. Still, in victory, human nature convinces us that we must have done many more things right than we did wrong, so there’s no need to sweat the small stuff.

In truth, victory and defeat is often a 51-49 proposition. That was certainly the case for most of my Super Bowls–they came down to the final drive, to overtime, to a kick with time expiring. A couple of plays go the other way in any one of those games, and history reads completely differently. But because it went our way 7 out of 10 times, does that suddenly mean we had way less to improve than whoever we were playing? Of course not!

The same goes for the US hockey team. An incredible, one-in-a-million stick save by Hellebuyck was the difference between winning and losing. Canada was faster all night and had fourteen more shots on goal; but the US had the killer save and the golden goal when it counted most. So who really has more to work on? The answer is, both teams have a lot they can improve. The only difference is the focus of their work.

How do you think you would respond to the mountain of work ahead for the Seahawks or the Patriots, for the US team or the Canadian team? Is it ‘hell no’ or ‘fuck yes’? Are you throwing in the towel or buttoning your chinstrap?

The people who say ‘no’ in a situation like this—with an opportunity to accomplish their goals or achieve their dreams—have let fear win. Fear of failure. Fear of struggle. Fear of pain. Fear of judgment. Fear of the unknown. In my experience, the majority of people are afraid of identifying their failures and self-identifying with the things they can’t live up to. This produces immense insecurity that a lot of people will do almost anything to avoid confronting or allowing to come to light. Exposing their vulnerabilities feels like a fate worse than death. The irony is, vulnerability is precisely what endears you to people and to teammates and makes you more receptive to learning; which in turn reduces fear and creates more opportunities for you to cut it loose, play free and succeed.

The Seahawks and the Patriots, the US and Canadian hockey teams, will not be afraid to tackle their next mountains. The guys who lead those teams are not afraid to do the work, to make the tough decisions, to take the big risks. The same is true for Alysa Liu and Ilia Malinin. Liu has been competing since she was 13. She bounced back from a sixth place finish at the 2022 Games to win Worlds last year and Olympic gold this year. Malinin has been a terminator his whole career, winning anything and everything. He’ll be back.

And now, they each have their own advantage over other teams and competitors if they take the time to learn the big lessons the Super Bowl and the Olympics can teach them. They either know exactly what it takes, or exactly what they’re missing. And they each have one less variable to manage than everybody else next month, next season, next Olympics cycle, which means we’re definitely not done hearing from them.


APPLICATION

“On the other side of your maximum fear are all the best things in life,” Will Smith said a few years back, after conquering his fear of heights and going skydiving.

Nothing truly great has ever been accomplished by people acting from a place of fear. Almost without exception, greatness is a product of acting in the face of fear. Of seeing possibilities where others see problems. Of picturing success instead of failure. Of not just rejecting the fear of failure, but rejecting failure itself as something permanent. Because failure is never the end. Only quitting is. Failure is just another opportunity to succeed at figuring something out and to build the self-confidence to try anything.

I know that’s very grandiose language. I can see how it might make you think that what I’m talking about here is only related to taking big, crazy swings on big, crazy things like skydiving or playing professional football or investing all your money into something. The reality is, conquering fear, getting comfortable with risk, and embracing your capacity to figure things out is the key to unlocking the full potential of anything you care about.

Winning with your team. Making money with your business. Learning from your education. Building camaraderie with your neighborhood. Finding deeper connection in pretty much any kind of relationship.

The depth and strength of your connection with your kids, for example, is defined in no small part by your willingness to be vulnerable and to not be afraid of honesty with them. You want them to practice what you preach. In some cases, you want them to do as you say but not as you did. You also want them to feel comfortable coming to you with anything, while deep down you pray it’s not for any of the uncomfortable stuff that’s better for their mom, or a guidance counselor, or the priest. What I can tell you is that the rewards you reap from holding space for their hard truths while being prepared to share your own with them, regardless of how uncomfortable or upsetting they might be, can literally last a lifetime.

And here’s the thing: if you’ve ever successfully faced down your fear of something–and it can be literally anything–then like Alysa Liu and the Seahawks, you know what it takes to do it again! Fearlessness is a transferable skill. You already know the level you need to get to and the work it’s going to take to get where you want to go.

Similarly, if you’ve tried and failed, and taken the time to look in the mirror, then like Ilia Malinin and the Patriots or the Canadian hockey team, you know who you are—warts and all. You already know what’s missing. You know the work you need to do on yourself to get to a place where the next time you see that mountain in front of you, and your first thought is ‘again!?’, your second thought is an immediate ‘fuck yes.’

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