It was a practice, not a game. Practice.
I looked up from around third base and saw my players hauling themselves up the steep hillside toward the soccer field. Heads down, huffing and puffing. That hill was no joke—more than a 45-degree incline, slick with mid-April drizzle. You had to descend it sideways like a goat or risk eating mud.
One of our players, who carried a little more weight, struggled more than the others. I acted like I didn’t notice, but I did. I wanted them all to feel the burn—to equate this climb with the suicide sprints in the gym.
“Carter, I got my eye on you!” I bellowed. “Just like in the game when you take innings off. Let’s do it again. GO!”
And off they went again after a 30-second break. I clicked the stopwatch, perched on a golf cart I used to haul gear down to the field.
I wasn’t a good coach. Not technically. That season we lost almost every game. At our school, baseball players weren’t always “baseball players.” Most hadn’t picked up a glove since Little League. My job—somehow—was to turn them into athletes. Or at least into a team.
But coaching, like teaching, is never just about skills or wins. It’s about transforming—not just others, but yourself. It’s about building trust, forging a shared identity, and occasionally doing something completely absurd, like making teenagers run up a mud-soaked hill to prove a point.
What those kids wanted more than anything was to get away—take the bus to some far-off Oregon coast town, like Astoria or Warrenton. Two hours each way from the West Slope of Portland. Far enough to feel like an adventure. They didn’t sign up for wind sprints. They signed up for something they couldn’t name—freedom, maybe. Camaraderie. Something that might resemble meaning.
I loved coaching. I really did. But I also wanted them to take it seriously. On those drizzly days, I’d push harder than I should. Because deep down, I wanted the game to mean something—not just to them, but to me. I wanted to belong to something worth building.
We had a few real ballplayers, but most were just trying to fulfill a sports requirement or avoid chemistry lab. Some days, we barely had nine players. I once had to call an athletic director to forfeit because we came up short. And when we did have a full roster? Substitutions were theoretical. Injuries? We played through them. Games could stretch into long, painful ordeals with scores that looked like football blowouts.
Still, I showed up. And so did they.
Looking back, I realize that so much of coaching is shaped by how we were coached—or weren’t—as kids. That’s why training matters. Why listening matters. A great coach, like a great teacher, doesn’t just transmit information or demand discipline. They ignite something. They help others discover what they’re capable of. They stay with you, even years later.
That first season was a lesson in humility. The players didn’t improve much that year. But they gave me their trust. Maybe they sensed I didn’t totally know what I was doing. But they still climbed that hill.
Eventually, I got better. I leaned on assistant coaches who had real baseball chops. I started listening more—to my captains, to the quieter players, to myself. I realized what mattered most wasn’t the wins—it was whether they enjoyed the game. Whether they wanted to come back.
In our third season, we tied the seventh-ranked team in the league. That was huge. We even won a few games. But what mattered more than the record was that we had become a team. We had grown into something together.
No more hill runs after that. I got smarter, too—discovered online clinics, watched videos, learned how to plan better practices. But mostly, I became a better coach because I stopped trying to be someone I wasn’t. I let the players be who they were, too.
Coaching, like any human endeavor, is about confronting your limitations and staying in the work anyway. It’s about adjusting—not just your strategy, but your spirit. The secret isn’t in the drills. It’s in the listening. In showing up. In caring enough to keep going, even when you lose by thirty runs.
Everyone could use a good coach.
Even good coaches.
Curated Listening:
The other great baseball song is from “The Boss.” I am still not quite sure what a speedball is, a non-drug one, that is. But here it is for the love of the game, it’s Bruce Springsteen’s “Glory Days.” Listen HERE. “Make you feel like a fool, boy!”