Building Up Your Educators Spiritually and Professionally
There are educators who teach subjects, and then there are those who shape hearts and minds.
Every once in a while, a school is graced with someone who refuses to stay within the boundaries of a computer screen or a classroom; someone who sees education not as content delivery but as formation. Formation of mind, yes, but also of heart, character, and calling.
When I served as a head of school, we had one of those rare individuals. He was an AP® English and AP® history teacher; brilliant, demanding, and unapologetically rigorous. Students knew from day one that his class would stretch them. He set a high bar, and he expected them to reach it. There were no shortcuts, no watered-down assignments, no easy A’s. He believed too much in his students to lower expectations. Yet, what made him unforgettable had very little to do with his syllabus.
Students called him “Captain.”
The nickname came from “O Captain! My Captain!”, the famous poem by Walt Whitman. It wasn’t something he gave himself. It was something earned and bestowed by the students he taught and mentored.
Why? Because like the captain in the poem, he led.
Not from a distance. Not from behind a desk. But among his students and in the trenches of their lives.
More Than a Teacher
You could find him just about anywhere except confined to a single role. He was at every home basketball and baseball game. He was not just sitting in the stands; he was present and invested. He didn’t stop there. He rode the bus to away games—think about that.
A seasoned AP® teacher grading essays that would intimidate most college students choosing to spend hours on a bus with high school athletes. Why? Not because it was required. Not because it added to his resume.
Because he cared.
He loved what he often called “the boys of summer.” But if you listened closely, you realized it wasn’t just about baseball. It was about who those young men were becoming. He saw beyond their stats and beyond their performance. He saw their potential.
And he gave himself to it.
The Diagnosis That Didn’t Define Him
Then came the news that no one wants to hear.
A terminal cancer diagnosis. It’s the kind of moment that stops everything. Reframes everything. Strips away what doesn’t matter and forces a reckoning with what does.
For many, it would have meant stepping away even retreating, but not for the Captain. He continued teaching right up until days before his passing.
Let that sink in.
Days. Not months. Not weeks. Days.
Even as his body weakened, his calling did not. Even as the weight of his diagnosis grew heavier, his investment in students never wavered.
In those final weeks, there was a sacred rhythm to his days. You would find him outside, throwing a baseball against the side of the school building. A simple act. Almost ordinary.
But it wasn’t—it was a picture of presence.
Students would pass by, and he would engage them, one conversation at a time. One word of encouragement. One moment of connection—quietly, one goodbye at a time. Not dramatic. Not self-focused. Just intentional.
He was finishing well.
The Day the Gym Became Sacred Ground
When he passed, the school community felt it deeply.
We knew his funeral couldn’t be held just anywhere. It needed to be in a place that reflected the scope of his impact, so we held it in the school gymnasium. It was the only space large enough to hold the students, families, alumni, colleagues, and friends whose lives he had touched.
The room was full. Heavy with grief, but also thick with gratitude.
As I stood to give the eulogy, I reflected on a life poured out. His was a life that had refused to be small, a life that had chosen presence over convenience and purpose over comfort.
And then something happened that I will never forget.
From the back of the gym, a student stood up. With a voice full of raw and unfiltered emotion, but deeply respectful, he shouted:
“O Captain! My Captain!”
For a brief moment, time stood still; and then, like a spark catching fire, another student stood.
“O Captain! My Captain!”
Then another. And another. Until, like popcorn across the room, students were rising to their feet calling out in unison: “O Captain! My Captain!” This wasn’t planned or orchestrated. It was the natural response of hearts that had been challenged and shaped. It was a tribute that no award, no plaque, no formal recognition could ever replicate.
It was legacy alive in the voices of students.
A Field That Still Speaks
Today, when I return to campus for sporting events, I often walk past the baseball field, and there, near the dugout, is a sign. The field bears his name—a fitting tribute for someone who never stopped showing up. Every time I see it, I’m reminded:
Buildings don’t carry legacies—people do; and programs don’t change lives—people do.
What Made the Difference?
It would be easy to romanticize his story without learning from it, but that would be a mistake. What the Captain modeled wasn’t accidental. It was intentional, and it’s replicable, not in personality but in posture. Christian school leaders don’t need to become him.
But they do need to learn from him.
Here are three strategies to help us make that kind of difference in our school communities:
- Lead with Presence, Not Just Position
The Captain understood something many leaders forget: Influence is built in proximity. He didn’t lead students solely through classes or assignments. He led by being where they were: games, hallways, bus rides, everyday moments.
Too often school leaders become functionally distant. Meetings pile up; responsibilities expand; and before long, leadership becomes primarily administrative rather than relational.
Yet, culture is not shaped in the office. It’s shaped in the spaces where life happens.
Practical ways to apply this:
- Show up consistently at student events or find ways within the virtual space to connect with people, not as a spectator but as a participant in the community.
- Intentionally enter student spaces without an agenda.
- Build in purposeful touch points: video, voice recordings, email, handwritten cards.
In-person or virtual presence communicates value, and when students feel valued, they become open to influence.
- Set a High Bar While Loving Deeply
One of the most compelling aspects of the Captain’s life was this tension:
He was both rigorous and relational.
In today’s educational landscape, there are often false dichotomies: 1) You can be demanding or compassionate; 2) You can uphold standards or build relationships.
He rejected that entirely. He believed students were capable of more, and he called them to it. They trusted him because they knew his expectations came from a place of deep care. Christian education, at its best, reflects both truth and grace. Not one or the other.
Practical ways to apply this:
- Set clear, high expectations academically and behaviorally while explaining the “why” behind them.
- Provide consistent feedback that challenges students to grow.
- Pair correction with encouragement. Students should know you are for them, not against them.
Students will rise to the level of expectation, especially when they know they are supported.
- Finish Well by Investing Intentionally
Perhaps the most powerful part of the Captain’s story wasn’t how he lived but how he finished. In his final weeks, he didn’t withdraw.
He leaned in.
Those moments outside, throwing a baseball and talking with students weren’t accidental. They were deliberate. He understood that legacy is built in intentional moments. To him, every conversation mattered, and each interaction counted. While most leaders won’t face the same circumstances, the principle remains:
You are always shaping your legacy.
Practical ways to apply this:
- Identify students who need intentional investment and prioritize time with them.
- Speak life-giving words regularly. Don’t assume students “just know.”
- End seasons, years, and relationships with intentional closure while affirming and encouraging those you’ve led. Finishing well isn’t about the last moment. It’s about how you steward the moments leading up to it.
The Call to Today’s Leaders
The Captain never set out to be remembered with a chant. He simply chose, day after day, to show up, to care, to change, and to invest. In doing so, he left a mark that still echoes. As a Christian school leader, you are shaping more than schedules and systems—YOU are shaping lives. The question is not whether you will have influence. The question is what kind. Will it be transactional and transformational, and will students remember what you managed or who you were?
One day, years from now, students will tell stories about your leadership and your school. They will remember the people who made a difference—the ones who saw them, the ones who believed in them, and the ones who showed up.
May we be leaders who earn, not demand, the kind of respect that echoes beyond our time. May there be moments, whether spoken aloud or held quietly in the hearts of those we’ve led, where the impact of our lives is captured in a simple, powerful tribute:
“O Captain! My Captain!”
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