Each summer, Catholic Memorial reads a common book, grades 7 thru 12. This year, it was The Boys in the Boat — Daniel Brown’s stirring account of nine young men from the University of Washington who rowed their way to Olympic gold in 1936. It’s a story that reads like myth: the poor kids beating the privileged, the overlooked outworking the favorites, the underdogs triumphing in perfection on the world’s stage.
And yet, as powerful as that story is, I’ve begun to wonder whether we, as educators, do students a disservice by sharing only tales that end in this way. The Boys in the Boat is about adversity and grit, yes, but it is also a rare example of everything falling miraculously into place. For every story like it, there are hundreds that don’t end in glory.
The truth is that most of life looks nothing like a storybook ending. And if our classrooms, assemblies, and lessons only highlight the winners, the medals, the school acceptances, and the highlight reels, we leave our students unprepared for the moments that actually define them: the disappointments, the losses, the quiet rebuilds.
I know, because I’ve lived them.
In the fall of 1992, I arrived at Dartmouth as a freshman goalkeeper on the soccer team. It was the culmination of years of work. It was my childhood dream realized. But midway through that first year, something shifted, I found myself a few rungs down on the depth chart and a couple of invitations to join the rowing team highlighted the idea that “we have choices” and maybe there were different challenges for me to consider. I didn’t know much about the sport, but I was curious.
Within months, I was hooked. By sophomore year I’d earned a seat in the varsity boat winning silver at Eastern Sprints, the sports’ championship for the best collegiate crews in the East. A solid junior year led to my election as CoCaptain for my Senior year, Everything I had worked for in grueling training was lining up for that storybook ending.
And then it fell apart.
Our boat struggled. We couldn’t find our rhythm. The coach made changes, searching for elusive speed. After some seat racing, he called me into his office and told me I was being moved to the junior varsity lineup just weeks before the final, regattas of the season. In our final races, I stood on the dock watching my teammates — my boat — leave the docks. It was an empty feeling, working hard, committing fully, and… coming up short. At 22, it certainly felt like failure.
In the four years following graduation, I had built a life that I loved as a teacher and coach. I taught science, coached soccer, basketball, and a rowing team that earned two National Championships. Still, the unfinished business of rowing lingered. I didn’t want my last chapter in the sport to be one of disappointment.
So, I applied to Oxford University, where graduate students can compete for spots on the famed “Blue Boat,” the varsity eight that races Cambridge each spring in the oldest intercollegiate competition in the world.
It’s hard to describe the magnitude of that race to an American audience. The Oxford-Cambridge Boat Race is broadcast live to millions. It’s four and a quarter mile long, with 250,000 spectators lining the banks of the Thames. Crews train forty hours for every minute of that race. Short of the Olympics, it is hallowed ground in the sport of rowing.
When I arrived in England, I had no idea what I was in for. Training was relentless: two practices a day, six days a week. The coaches stripped down my rowing stroke and rebuilt it from scratch. Sports scientists drew blood samples to measure lactate thresholds. We became machines.
Of the 32 men who started training, half were cut within the first month. By February, the final lineup was announced: my name was called for seven seat; the technical seat that sets rhythm for the starboard side. It was one of the proudest days of my life.
Then came March 24, 2001: Race Day.
Poised on the starting line, I had expected to feel anxious — but instead, I felt calm. When you’ve prepared as fully as possible, there’s a peace in knowing you’ve done everything you can.
“Attention… Go!”
A few hundred meters into the race, the unthinkable happened. The umpire stopped the race, something that hadn’t occurred in its 147-year history. A Cambridge rower had lost his oar in a clash of blades. When the race restarted, we had lost the inside bend. We fought back but never recovered. Cambridge crossed the line first. The British have a word for it: gutted. It captures that hollow, sickening feeling of loss when you’ve given everything and still come up short.
I don’t tell that story often. Even now, it hurts. But I share it because it taught me more than any victory ever did.
At Dartmouth, I thought I knew what hard work meant. At Oxford, I learned what total commitment meant. This is the kind that asks everything of you, even when there’s no guarantee of reward, and when the stakes seem so much higher because the stage is public.
Those experiences taught me that commitment isn’t something you get because you win. It’s what carries you forward in every other moment. My disappointments, my failures taught me that we are not defined by these moments, but instead by the moments that follow. They taught me that when everything falls apart, what holds you together are the people beside you.
The men I rowed with remain some of my closest friends. They stood next to me at my wedding. They’re the ones I call when life gets hard. That’s brotherhood. It isn’t some motto on the bottom of a shield or a shiny word on a school banner, but instead, it is the lived truth of showing up for one another when things go sideways.
In education, we celebrate the 4.0s, the championship trophies, the perfect college admissions letters. And yes, students should see examples of excellence. But they also deserve to see what happens when excellence doesn’t translate to victory.
We need to normalize stories of effort without reward and the reality that sometimes you do everything right and still lose. Not because of lack of talent or drive, but because life is unpredictable.
When we hide those stories, we rob our students of resilience. We make them believe that success is linear, that good effort guarantees good outcomes. And then, when life inevitably delivers its blows, they think something is wrong with them.
But if we share the full truth, that growth is forged in the uncomfortable, unseen, often painful moments, we prepare them for the world they’ll more realistically live in.
So yes, I was gutted... twice. But those two losses built the foundation of who I am today: an educator who believes that the most important stories we can tell our students are the ones that end not in gold, but in grit. The world loves the storybook ending. But the better story, the one that shapes and forms us, is often the one that hurts.
Because sometimes, success doesn’t look like crossing the line first. Sometimes, it looks like the quiet act of finishing a race you didn’t win — and showing up again the next day.