Road vs. Trail: Lessons in Endurance and Leadership

This morning I ran a half marathon after months of trail training. It was harder than I expected. Trails give you natural breaks and you can switch to a hike on the ascents, recover on the descents, and let the terrain give you some breaks. On the road, it’s different: 13.1 miles of nonstop running. No pause button. The physical challenge was real, but the mental grind of not getting those “trail pauses” was even tougher. And not surprisingly, my time was not as good as last time.

And because I had 13.1 miles alone with my thoughts, I tried to discern some leadership lessons:

1. Different running disciplines build different muscles.
I’ve been logging plenty of trail miles lately, and I thought that would carry me through a road race without much trouble. Wrong. The strength and agility that trails demand don’t automatically translate to the rhythm and consistency of road running.

Leadership is the same. As one of my clients, Vaital, manages three distinct lines of business, including AI services, AI strategy workshops, and an AI SaaS product, each LOB requires a different set of muscles. Excelling in one doesn’t guarantee strength in the others. Leaders have to execute intentionally for each area rather than assuming success will automatically transfer from one to the other.

2. Endurance is contextual.
On the trail, endurance means grinding up steep climbs, running across uneven ground, and adapting to whatever the terrain throws at you. On the road, endurance means locking into pace, holding rhythm mile after mile, and resisting the urge to slow down when you get tired.

Leadership is no different. A good example is one of my clients, Venteur, who is preparing for a busy Open Enrollment season, the critical annual window when employees across the U.S. choose their health insurance benefits. For their team, endurance isn’t about bursts of creativity or innovation; it’s about sustaining focus, execution, and customer support over weeks of intense demand. At other times, endurance may mean navigating turbulence or rapid change. Both forms of endurance are essential, but they require different energy and mindset.

3. Cross-training matters.
If I only train on trails, my road running suffers. And if I only run roads, my trail strength lags. It’s tempting to stick with what feels comfortable, but that leaves blind spots.

Leadership works the same way. If leaders only practice one style, say, vision-setting in growth mode, or disciplined execution in steady state, they’ll be caught off guard when circumstances change. The leaders who deliberately cross-train by stretching into unfamiliar roles, industries, or challenges develop range. That range is what allows them to adapt and respond effectively when the unexpected inevitably shows up.

This morning’s half marathon was humbling. But that’s part of why I keep signing up for races and events like 29029: they remind me that growth often comes from switching disciplines, adapting endurance to context, and forcing myself to train in ways that don’t come naturally.