Throughout my tenure as an administrator, I can count on both hands the times I drove to work hours earlier than my staff and students, wrapped in intentional silence. The stillness of the air was intentional because I was uncertain. Unsure. Lost. Lonely and paused in a daze. Whether it was processing a preemptive conversation with staff members about racial perceptions, differing philosophies on the care for young people, school threats, political instability, investigations, health crisis, pandemics, bigotry or the isolation of leadership. In those moments, I knew once my vehicle reach it’s destination, a decision had to be made, an action enforced, or pursue the truth through a thicket of lies, deception, and deceit. As I walked through the threshold, I know for certain that futures were in my hands. I also understood something profound about the ancient words that would later save me: “The Lord is my shepherd; I shall not want.” But first, I had to reckon with the fundamental question that haunts every leader in their darkest moments—who leads the leader when the leader doesn’t know the way?
Shepherd Leadership
Leadership, at its most honest, is an exercise in controlled chaos. We stand before rooms full of expectant faces, bearing the weight of dreams deferred and promises made. The decisions we make ripple outward in ways we cannot fully comprehend, touching lives and altering futures. In these moments, the psalm’s pastoral imagery might seem quaint, even irrelevant. What does a shepherd’s rod have to do with navigating workplace volatility or organizational silos?
Mathematics of Trust + Rest
This mathematics reveals itself most clearly in the psalm’s next movement, where the shepherd’s wisdom about sustainable leadership emerges. But the psalm is not about sheep—it is about the mathematics of trust, the precise calculation of vulnerability that every authentic leader must master. Trust, like mathematics, follows certain immutable laws. It compounds slowly and dissolves quickly. It requires both courage and wisdom to invest properly, and the patience to wait for returns that cannot be rushed or manufactured.
“He makes me lie down in green pastures; he leads me beside quiet waters.” Here is the paradox that modern leadership mentors miss…sometimes the most radical act is rest. The shepherd is intentional to resist driving the flock to exhaustion in pursuit of the next meadow. This is something I struggled with early on in my leadership. I felt the only way to make an impact and drive change was to drive myself into the ground. There is wisdom in the pause. Wisdom in courage and wisdom in separating urgent from essential.
The Valley
The valley is not metaphor—it is geography. It is the place where leadership strips away its pretensions and reveals its essential nakedness. David knew this terrain intimately. He had felt the cave walls closing in around him, had tasted the bitter salt of his own tears mixing with the dust of his hiding places. When he writes of walking through the valley of the shadow of death, he speaks from the authority of someone who has felt death’s cold breath against his neck, who has understood that leadership, at its core, is about moving forward when moving forward feels impossible.
The valley teaches what the mountaintop cannot. Success breeds confidence, but confidence is not wisdom. The valley strips away the comfortable illusions of control, the neat narratives of cause and effect that we tell ourselves in boardrooms and strategy sessions. It is in the valley where we discover that our carefully crafted five-year plans are often just sophisticated forms of wishful thinking. Here, in this place of shadow and uncertainty, we learn that leadership is not about having all the answers—it is about having the courage to ask the right questions and the humility to admit when we are lost.
But the valley is also where character crystallizes. It is where we discover whether our leadership is built on the solid foundation of service or the shifting sand of ego. The tests that come in the valley are not the clean, quantifiable challenges of quarterly reports or market analysis. They are messier, more human—the phone call at 2 AM about a team member’s family crisis, the decision between what is profitable and what is right, the moment when loyalty and integrity pull in opposite directions. These are the crucible moments that forge leaders worthy of the title, or reveal those who merely wear it as costume.
Radical Hospitality
“You prepare a table before me in the presence of my enemies.” This line has always struck me as peculiar. Why a table? Why not a fortress or a fortified wall? But perhaps this is the point. Leadership, at its best, is an act of radical hospitality. Even—especially—when surrounded by those who would see us fail, we continue to create space for others. We set the table. We break bread. We insist on our shared humanity even when the world insists on our separation. The table becomes an act of defiance against these internal accusations. We choose to show up anyway. We choose to lead anyway. We choose to serve anyway.
Both + And
The wilderness will come. The valley will test us. The enemies—internal and external—will make their presence known. But in these moments, whether we find our anchor in ancient psalms, Buddhist teachings on compassion, the ethical imperatives of secular humanism, or the simple recognition of our shared humanity, the call remains the same. We are summoned to lead not from a place of certainty, but from a place of hope. Not because we have all the answers, but because we have learned to trust the process of seeking them together.
The sacred, whatever form it takes in our lives, offers not escape from leadership’s burden but orientation within it. Not answers but the right questions. Not certainty but the courage to continue walking, one step at a time, through whatever darkness awaits.
When we choose service over self-interest, when we set tables instead of building walls, when we remember that the highest form of leadership is simply showing up, again and again. Sooner or later, I will walk across the parking lot to get back in my car and drive back home. With keys in hand and renewed faith, I peer at my reflection in the rear view mirror and say to myself, “look what God did.”
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