When the Trail Only Fits One Jeep

A leadership lesson from the White Mountains of Maine

Bethel, Maine, in the fall feels like it was designed on purpose. The leaves change just enough to remind you that time is moving, the mornings are cool and crisp, and the afternoons are comfortable in a way that makes you forget winter is coming. That was the setting for a two-day Jeep off-road adventure in the White Mountains—one I shared with my wife, Kim, and two other couples we’d met on a similar trip two years earlier.

There were about 180 Jeeps in total. It wasn’t just an event; it was a temporary community. People from different backgrounds, skill levels, and experiences all came together for three days of trails, stories, and shared problem-solving. The plan was simple: two days, two trails, each progressively more difficult than the last.

What I didn’t plan on was a leadership lesson delivered from underneath my Jeep.

The Problem You Can Feel—but Can’t Name

On the final day, deep into a wooded trail, my Jeep Wrangler stopped behaving like it normally does. Nothing dramatic at first. The engine was running. The Jeep was still moving. But something felt wrong.

As I pressed the accelerator, it required more power than usual—almost like something was holding the vehicle back. We were on about a 15-degree incline, not exactly the place you want to stop and diagnose a mechanical issue. And because the trail only allowed one vehicle at a time, stopping didn’t just affect me—it affected everyone behind me.

That’s when the real pressure set in.

The hardest part wasn’t fear. It was uncertainty.

I didn’t know what the problem was. And if I couldn’t identify the problem, I couldn’t know the fix. And even if we figured out the fix—could it be done right there, on the side of a trail, 350 miles from home?

I crawled underneath the Jeep while Kim stayed inside. Other Jeep owners gathered around. More eyes. More experience. More perspectives. But no immediate answer.

The Jeep could still move, so we made the decision to push forward to a clearing farther up the trail. As we climbed, nothing improved. When I finally stopped, the left rear wheel was smoking. If you’ve ever smelled overheated brakes, you know there’s no mistaking it.

Now we had clarity.

Leadership Without Titles

With space to work, the group self-organized almost instantly. No one called a meeting. No one announced they were in charge. Leadership showed up as competence, not volume.

One person assessed the caliper. Another asked for specific tools. Jesse—one of the friends we’d eaten barbecue with just days earlier—pulled out a pair of vise grips from his Jeep. Someone else produced a pry bar. Zip ties appeared.

Watching it unfold felt like observing a team of surgeons during a trauma case. Different roles. Different experience levels. One shared objective.

There was also a contrast that stood out clearly.

Some people were vocal but not particularly helpful. They jumped to complex explanations before the basics were ruled out. Ego crept in. Meanwhile, the people with real experience asked simpler questions and worked methodically.

The solution turned out to be straightforward: a seized rear brake caliper. We pried it open, pinched off the hydraulic line with vise grips, zip-tied them in place so they wouldn’t fall off, and disabled that brake entirely.

It wasn’t pretty. It wasn’t permanent. But it worked.

That temporary fix carried me 20 miles back to base camp—and another five hours home to Albany the next morning—with only three functioning brakes.

Déjà Vu on the Trail

Later that same day, another Jeep died on the trail entirely. Engine off. No movement.

This time, the response was faster. Smoother. Confident.

A tow strap came out. Another Jeep backed down the trail and pulled the disabled vehicle to a clearing. Tools and parts surfaced again—almost on cue. The group changed a fuel filter, added a couple gallons of gas, and got the Jeep running.

What struck me was how calm everything felt.

The situation was no less serious, but the team was already formed. Trust had been built through shared effort earlier in the day. There was no panic—just execution.

At that moment, I realized this weekend wasn’t about Jeeps anymore.

The Leadership Lesson the Trail Teaches

The single leadership principle that stood out was teamwork—but not the kind that shows up on motivational posters.

This was teamwork grounded in:

• Willingness to help without recognition

• Experience speaking louder than ego

• Creativity over technical overcomplication

• Trust in others when you don’t have the answer

It also reinforced something subtle but important: focus on the task at hand.

That last trail was optional. An add-on. We didn’t need to do it. And yet, by expanding the scope just a little, we increased the likelihood of failure. Leaders do this all the time—adding “one more thing” without fully accounting for risk.

Sometimes progress isn’t about doing more. It’s about knowing when enough is enough.

Bringing It Back to Leadership

In business, leadership, and life, breakdowns rarely announce themselves clearly. More often, they feel like something is “off.” Performance drops. Resistance increases. Progress slows.

Great leaders don’t pretend they have all the answers. They invite other perspectives. They let expertise—not ego—drive decisions. And they understand that the goal isn’t looking competent; it’s getting everyone safely off the trail.

The Jeep didn’t make it home perfectly. But it made it home because a group of people—many of whom were strangers just days earlier—worked together when it mattered.

That’s leadership.

Not loud.

Not polished.

Just effective—when the trail only fits one Jeep.