article · Motorcycling, Business, Travel, Personal
The Roads That Teach You Something
After twenty years in business and just as many on two wheels, the best lessons in leadership come from the most unexpected roads.
There's a stretch of highway in southern West Virginia where the road drops off a ridge and descends into a valley so deep that the light changes. The canopy closes overhead, the temperature drops ten degrees, and for a few minutes, the world shrinks to just you and the machine beneath you.
I've ridden this road dozens of times. Each time, it teaches me something different.
Why Some Roads Matter More Than Others
Not every road is created equal. Some roads are purely functional — they exist to move you from point A to point B with maximum efficiency and minimum engagement. Interstates, mostly. Four lanes of sameness punctuated by gas stations and identical exits.
But other roads demand your attention. They curve when you don't expect it. They climb when the map suggests they shouldn't. They drop you into towns that time forgot, where the general store still has a wooden floor and the coffee costs a dollar.
These are the roads that teach you something.
What Riding Teaches About Leadership
After twenty years in business and just as many on two wheels, I've come to believe that the best lessons in leadership don't come from boardrooms. They come from the moments when you're genuinely uncomfortable — when the road is unfamiliar, the weather is turning, and the only map is the one in your head.
On a motorcycle, there's no committee to consult. No slides to review. You read the road, you make a decision, and you live with the outcome. Every corner is a commitment.
The best leaders I've known ride the same way — they read the terrain, commit to a line, and adjust mid-corner when necessary. They don't freeze. They don't look at the guardrail.
The Case for Slowing Down
In business, we worship speed. Ship faster. Move faster. Decide faster. And there's merit in that — paralysis kills more companies than bad decisions do.
But on the road, speed is just a number. What matters is pace. Pace is the rhythm of your day — how long you ride, where you stop, what you notice. A rider going 45 through a mountain hollow sees more than the one doing 85 on the interstate.
The same is true in business. The leaders who build things that last aren't necessarily the fastest. They're the ones who know when to slow down, when to stop, and when to sit on a stone wall and look at the view before deciding which way to go next.
The Road Ahead
I'm writing this from a small motel in Marlinton, West Virginia. Tomorrow I'll ride the Highland Scenic Highway — one of the finest roads in the eastern United States. I don't have a schedule. I don't have a destination beyond "north, eventually."
That's the luxury of a road trip and, increasingly, how I think about the next phase of my career. Not a rigid plan, but a direction. A willingness to see what's around the next bend.
Some roads teach you where to go. The best ones teach you how to travel.