When I moved to Virginia in 2020, running changed shape for me. The shift was practical at first. Good trails were close by, and a welcoming trail-running community made it easy to trade pavement for dirt and switchbacks. Before long, what started as a way to explore a new place became a steady practice, and that practice gradually pulled me toward longer efforts and bigger days.
Over the last few years, I stepped into the world of trail ultramarathons, finishing five races in the thirty-to-thirty-five-mile range. Most recently, I covered fifty miles in a backyard ultra, the kind of event that asks for patience as much as grit. There is no single dramatic moment when ultrarunning “begins.” It arrives in small decisions that accumulate, until one day you realize you are no longer just going for a run. You are training for something that will test your attention, your planning, and your willingness to stay with discomfort longer than you thought you could.
The farther the miles stretched, the more space there was for thought. Long runs have a way of creating quiet without demanding silence. They make room for questions you do not always have time to hold during a normal workday. Somewhere between the rhythm of footfalls and the steady recalculation of effort, I began noticing how often the experience of leading mirrors the experience of going long. Both can feel straightforward from the outside, and both can become deeply complicated once you are inside them.
The “Pain Cave” and the Work No One Sees
Alongside my running life, I serve as an associate dean at James Madison University. That role has provided its own miles, just measured differently. Leadership in higher education carries moments of purpose and clarity, but it also contains stretches that feel like grind, where the path narrows and the effort becomes mental as much as logistical. It is in those stretches that I kept returning to an idea from ultrarunning that refuses to stay in the realm of sport.
Ultrarunner Courtney Dauwalter has described part of her success as tied to a willingness to enter what she calls the “pain cave.” The phrase lands because it is vivid, but also because it is familiar. In running, the pain cave is the point at which comfort leaves the conversation. It is where the body starts offering reasons to stop, where doubt gets louder, and where the finish line may still feel far away. The runner cannot pretend it is pleasant, but can choose to keep moving through it.
Leadership can contain an equivalent terrain. Certain responsibilities, conflicts, or decisions can feel like a professional version of that cave, not because the work is inherently negative, but because the moment demands more than routine capacity. It may require endurance when outcomes are uncertain, composure when opinions collide, or steadiness when there is no quick fix. The lesson is not that leaders should seek suffering, or romanticize hardship. The lesson is that uncomfortable periods are part of the job, and that how a person approaches those periods often determines what happens next.
Watching how elite athletes speak about discomfort can clarify what many leaders already sense. The hard part is rarely the first mile. The hard part is what follows the first wave of fatigue, after the initial motivation has been spent. In those moments, there is value in a mindset that does not panic at pain, does not treat difficulty as proof of failure, and does not confuse discomfort with danger. That mindset does not make the cave disappear. It simply allows you to enter it without losing your ability to think.
Why Metaphors Matter, With One Important Caveat
Metaphors are not decoration. Used well, they help people understand leadership more clearly, and they can sharpen the way we communicate the skills and habits of mind that leadership requires in higher education. They offer a language that many people intuitively recognize, even if they have never stepped on a trail. The body’s experience becomes a bridge to the mind’s experience. The trail becomes a way to talk about uncertainty, persistence, and judgment without reducing those concepts to slogans.
That is why ultrarunning, despite its extreme edges, can still offer useful images for administrators and for those who lead in less formal ways. The metaphors do not belong only to department heads, chairs, or deans. They can resonate in committee work, in faculty mentoring, and in the many quiet roles where influence is earned through consistency rather than title. Not every act of leadership is public, and not every victory comes with an announcement. Ultrarunning understands that. Much of the effort happens away from spectators, and much of the work is invisible unless you have lived it.
Still, it is worth naming a caution before leaning too heavily on the comparison. Steve Friedman, writing in Runner’s World, points out that ultrarunners often sit at the far ends of the bell curve. In his description, they can be unusual in their drive, zeal, and habits, and he lists types that range from recovering addicts and everyday obsessives to those fueled by a relentless need to prove something, along with plenty of plain, occasionally pleasant, sometimes grouchy, and remarkably fit oddballs.
That perspective is fair, and it keeps the metaphor honest. We do not need to mirror the full collection of ultrarunner traits to learn from the sport. The point is not to imitate a personality type, or to assume that intensity is the only path to excellence. The point is to borrow what is useful and leave the rest. A metaphor works best when it invites reflection, not when it demands that everyone become the same kind of person.
In the end, the value of the pain cave is not that it turns someone into an ultrarunner, or that it turns a leader into an athlete. Its value is that it names something many people already face: the moment when a task becomes truly hard, when the easy strategies stop working, and when you must decide what kind of steadiness you can practice. On the trail, you keep moving forward, step by step. In leadership, you do the same, decision by decision, staying present even when the work feels like it has narrowed into a cave.
