Wandering with Purpose: The Real Terrain of Transformational Leadership

There’s a comforting illusion many people carry into leadership—that if you’re doing it right, the journey will be clear, the path smooth, and the people supportive. But anyone who has ever led through meaningful change—especially in the church—knows otherwise.

“The best guide for any journey is one who has made the journey himself—perhaps multiple times—and thus knows something about the terrain, the climate, the beauty, dangers, and challenges at each point along the way.”

Leadership is rarely linear. It’s more like a winding trail through desert terrain, where even the mapmakers have left few notes. And yet, this is where some of the most sacred and transformational work happens—in the wilderness.

Henri Nouwen once wrote, “The great illusion of leadership is to think that man can be led out of the desert by someone who has never been there.” That quote has stayed with me over the years. It reminds me that true leadership doesn’t come from credentials or charisma—it comes from experience. From pain. From the long, slow walk through seasons where you’re not sure what’s next, but you’ve seen enough to trust that God is still at work.

Leading Through Turning Points (and the Chaos That Follows)

There’s a common misconception that once people get clarity, the hard part is over. But in truth, the moment after clarity can be the most chaotic. You’ve helped your people name what’s broken. You’ve identified the next faithful step. Hope surges. Momentum begins to build.

Then…the wilderness.

You’re no longer debating what to do, but you’re also not entirely sure how to do it. That initial spark of freedom and energy starts to fade, and you’re left with the reality of the work ahead. People start to question the direction. Some even turn their questions into accusations.

Sound familiar?

God often leads us the long way around. Not because He’s inefficient, but because He’s wise. If we were hit with the biggest challenges right out of the gate, we’d lose heart. So God gives us easier early victories—not to deceive us, but to prepare us. To preserve us.

“God often takes us the long way to preserve us and prepare us for the entire journey.”

But from the outside, and even to those following you, it may look like aimless wandering. Moses knew this better than anyone. The people who once celebrated their deliverance from Egypt soon turned on him. “Why did you bring us out here to die?” they cried.

The problem wasn’t the direction. It was the fear. When people get pushed to the edge of their fear, things unravel quickly. Like the tragic stories of human stampedes, there’s something deep within all of us that panics when we can no longer see the ground beneath our feet.

It Feels Personal, Even When It’s Not

When I reflect on leading turnaround efforts in congregations I’ve served, I see this wilderness pattern clearly. At the beginning, there’s energy. Enthusiasm. Possibility. Then we step into the wild. Things get harder before they get better. That’s when the arrows start flying—usually at the leader.

I’ve had board members actively undermine ministry efforts—not because they were evil or malicious, but because they were afraid. They couldn’t see the future yet, and the present didn’t look like the past. That fear turned to frustration, and frustration turned to sabotage. It’s easy to take it personally. Sometimes it feels personal. But often, it’s just pain spilling out in strange ways.

I remember one instance when a board member erupted into a profanity-laced tirade—not over policy or theology, but because the Wi-Fi “wasn’t working” (though it actually was). Everyone saw it. Everyone heard it. It was absurd on the surface, but underneath was something real: fear, grief, and a sense of powerlessness.

“People experience real pain and real fear. It may be manifested in weird ways, but it is true nonetheless.”

The Long Way Is the Transforming Way

Leadership in God’s direction is not a straight shot to success—it’s a slow, sacred wandering. We loop. We backtrack. We summit mountaintops only to descend into valleys. But if you look closely, you’ll see how God is shaping something in the people…and in you.

As leaders, we’re tempted to think our job is to make people happy while following God’s path. But that’s a false tension. Our job isn’t to keep people comfortable—it’s to help them be faithful. Happiness is fleeting. Faithfulness builds something that lasts.

“Our first priority is to follow the path God calls us on, and lead people on the journey as faithfully and gracefully as we are able—with God’s help.”

Sometimes the journey looks like failure. Sometimes it looks like loss. But if God is in it, there’s a deeper transformation happening—one that’s not always visible in the moment.

A Word to Leaders in the Wilderness

If you’re leading through change right now—if you’re deep in the wilderness—hold fast. You are not lost. And you are not alone.

Your job is not to have all the answers. It’s to stay close to the One who leads cloud by day and fire by night. Your credibility as a leader doesn’t come from perfection; it comes from having walked the path. You’ve been in the desert before. You’ll make it through again.

And maybe, just maybe, someone behind you will find their courage because they saw you walk it first.