Taking the Long Way
Road Trips & Leadership Lessons
For many, Memorial Day is both a time to honor fallen service members and the unofficial start of summer. Here in Wisconsin, we’re finally thawed out from winter and looking ahead to vacations, staycations, and time outside. For my family, both growing up and now as an adult, summer usually includes at least one good road trip. Over the years, I’ve realized that road trips do more than take us somewhere; they give us space to bond, build relationships, see new things, and even learn lessons about ourselves. I’ve found that when life moves fast, road trips have challenged me to slow down, pay attention, and simply be.
Some of the most memorable road trips I’ve taken were the long ones: from Wisconsin all the way to Los Angeles for the ’84 Olympics, or to Yellowstone to run my first half-marathon. These drives not only gave me time with my thoughts, they also created opportunities for conversations that otherwise may not have happened. Each trip taught me something about myself and about the people I was traveling with.
The Gift of Windshield Time
On a road trip, you’re almost forced to spend real time together. You’re stuck in a car together, and whether it is three hours or thirty hours, there is something powerful about being in a vehicle with people and having to navigate the journey as a team. You make decisions together about where to stop, when to eat, when to fill up, and whether it is worth taking the scenic route. You may have a shared destination in mind, but you still have to figure things out as you go.
Like any job or team that I’ve ever been a part of, I’ve learned that leadership is not just about knowing where you want to end up; it is also about learning (and evolving) how you want to move forward. The best road trips have taught me many lessons that parallel my own personal leadership journey: patience, how to navigate the unexpected, and how to give conversations room to breathe and develop.
Seemingly endless miles on the road can create the kind of space where courageous conversations can happen—conversations we may have been avoiding or wanting to rush because of the pace at which we live our daily lives. But with fewer distractions and by simply sitting alongside one another, there is room for honesty, listening, and connection.
It took a friend and me nearly nineteen hours to drive to Yellowstone National Park. We could have flown there in just a few hours, but we would have missed the gift of that time together. We talked about far more than we usually did, even though we lived just a few minutes away from one another. Without the usual interruptions of work, screens, schedules, and responsibilities, we had room to talk about what was really going on in our lives. We laughed hard. We shared stories. And, unexpectedly, we shared tears as my friend was navigating a particularly difficult season of life.
I’ll never forget that trip for as long as I live. It taught me the importance of slowing down and staying present long enough for trust to deepen.
Navigating the Unexpected
Road trips also remind us that unexpected things happen. A missed turn, a flat tire, bad weather, or even an unplanned trip to the ER can suddenly change the day. Yet those moments often become the stories we tell later. They’re the moments that test us, shape us, and even make us laugh once the stress has passed. In life, and in leadership, how we respond to the unexpected is what defines us. You can have the most articulate worldview about leadership, but only when you can face the unexpected head-on—and not see every disruption as a failure—will you embody a style of leadership grounded in mindful resilience.
Having hours of windshield time together also requires us to both take the wheel and be willing to ride as a passenger. In leadership, there are moments to step up, make decisions, and guide others, and there are moments to trust someone else, listen, and let another person lead.
If road trips can teach us something about leadership, then maybe they can also remind us what to practice. As leaders, we can learn to ask better questions instead of assuming we already know the route. We can make time for conversations that matter, even when they are difficult. We can notice who needs a break, who has been carrying too much, and when it is time to switch drivers.
We can stay calm when plans go awry because people look to leaders for steadiness in moments of uncertainty. We can build in margin instead of packing every minute, and learn to leave room for rest, reflection, and the kinds of unplanned stops where our imagination can expand.
Growing Something That Lasts
Leadership is not just about getting people to a destination as quickly as possible; it is about growing something that can be sustained for the long journey. A road trip gives us a simple place to practice those habits.
At the Solidago Institute, we’re on a journey, and we’re excited to be growing a wider community to journey together. Whether it’s grabbing coffee, joining a cohort, or maybe someday on a car ride, reach out if you want to hone your leadership skills. We want to be along for the ride as you reach new heights while also caring for your organization’s health and well-being.
