The Road's Hard Truths: Leadership Lessons from tackling 4,300 Miles in the Saddle
There's something brutally honest about the road. No corporate jargon to hide behind. No boardroom walls to contain your mistakes. Just you, a machine, and consequences that arrive at highway speed.
If you are new here, I'm currently riding 4,300 miles across six countries for RisingUnited.org and the Hera Rising Mission - championing equality and STEAM education. But this isn't about the cause (though it's a damn good one). This is about what happens when theory meets asphalt, when leadership principles get tested in dust, rain, and unexpected detours.
Here's what the road has reinforced, one mile at a time:
1. Plans Are Just Elaborate Guesses
That meticulously plotted route? That carefully crafted strategy? The universe sees your plans and raises you a washed-out road, a military checkpoint, or an unexpected border closure. The leaders who survive aren't the ones with the perfect plan – they're the ones who can toss that plan aside without ceremony when reality demands it.
The Guatemala border crossing taught me this lesson again last week. Sometimes you pivot, sometimes you wait, sometimes you find another way entirely. But you never, ever just stand there clutching your outdated map while insisting it should work.
2. The Myth of the Solo Hero Is Just That – A Myth
The image of the lone rider conquering the highway makes for great marketing. It's also complete fiction. Every mile of this journey has reminded me that behind every "solo" achievement stands a network of support, knowledge, and assistance.
The best leaders understand this instinctively. They build teams, foster connections, and know when to ask for help. Whether it's a local mechanic who knows the quirks of your bike better than you do, or team members who bring perspectives you'd never consider – no one crosses the finish line alone.
3. Discomfort Is Where Growth Lives
The road doesn't care about your comfort zone. Neither does meaningful leadership. Those pre-dawn starts in freezing rain, the scorching afternoon stretches with no shade, the unexpected mechanical issues – they're all just variations on the same lesson: discomfort is inevitable on any journey worth taking.
Great leaders don't seek comfort; they seek progress. They understand that growth happens precisely at the point where ease ends and challenge begins. The question isn't whether you'll face discomfort – it's what you'll do when it arrives.
4. Details Matter More Than Grand Gestures
A loose bolt, an overlooked weather report, a misread sign – small things determine success or failure on the road. Leadership works the same way. It's rarely the dramatic decisions that define great leadership but rather the consistent attention to seemingly minor details.
The conversations with locals who know which route to take when the main road floods. The extra five minutes spent checking your equipment. The genuine interest in someone's background before asking for their help. These aren't small things – they're everything.
5. The Journey Is the Whole Point
If reaching the destination is your only measure of success, you're missing the entire purpose of the ride. This applies to leadership perhaps more than anything else. The goal matters, but, it's the journey – the learning, the connections, the evolution, your contributions – that creates real value.
When a trip becomes only about ticking boxes and logging miles, it loses its soul. When leadership becomes only about metrics and outcomes, it loses its humanity. Neither is sustainable, and neither is worth the effort.
This ride for equality has been more than a journey; it's been a masterclass in leadership without safety nets. The kind that doesn't come from books but from dirt under your nails and sweat in your eyes. The kind that teaches you that commitment isn't about words but about pushing forward when every instinct tells you to stop.
What leadership lessons have your own journeys—on or off the road—taught you?
