Uncharted Moments: What Lewis & Clark Still Teach Us About Leadership, Listening, and Love – Episode 70

 

 

I sat down with Jeff Ton expecting a conversation about leadership and history. What I didn’t expect was how much we’d end up talking about attention, where we place it, how rarely we slow down, and what happens when we actually do.

 

Jeff calls himself a “hippie coder turned CIO,” and that range alone tells you he’s lived in very different worlds. Over time, his love of leadership and fascination with Lewis and Clark merged into something more personal, eventually culminating in a book he’s finishing now called Uncharted Moments. It’s not out yet, but after reading an early version and talking with Jeff, I can tell you this isn’t a typical history story.

 

Leadership Without A Clear Map

One idea we kept coming back to was uncertainty. Jeff reminded me that Lewis and Clark carried a map that labeled most of the western territory as “conjectural.” Unknown. That didn’t stop them from moving forward, but it did require vision, trust, and adaptability.

 

That challenge feels familiar today. Leading without perfect information isn’t a new problem, but it’s one we often forget has been solved before, by people who understood the value of relationships and shared purpose.

 

Listening Changes The Story

One of the most compelling parts of our conversation was about listening. Jeff talks about how his understanding of the expedition shifted when he stopped seeing it as a story of discovery and began to see it as a story of relationships, especially with Indigenous tribes who already knew the land.

 

That shift didn’t just change how he understood history. It changed how he approached leadership, learning, and even his own marriage.

 

Uncharted Moments

Jeff uses the phrase “uncharted moments” to describe the experiences you can’t plan for, the ones that don’t announce themselves as important until much later. They’re the moments you only notice if you’re willing to slow down, take the side road, or stay curious a little longer than usual.

 

It’s a simple idea, but one we don’t practice often enough.

 

Where Are You In The River?

Jeff shared a metaphor that I think many leaders will recognize. Imagine your team in a river, navigating the current every day. Sometimes you need to be in the water with them. Sometimes you need to be on the bank helping them find a way through. And sometimes you need to step back far enough to see the whole valley.

 

Leadership isn’t about picking one role. It’s about knowing when to shift.

 

Try This Week

Take five quiet minutes and ask yourself:

• Where am I rushing past something worth noticing?
• Where do I need to listen more rather than pushing ahead?
• Where am I in the river right now, and where does my team need me to be?
  

Listen To The Episode

Jeff’s book Uncharted Moments isn’t out yet, and we’ll share more when it’s released. For now, the conversation and Jeff’s website are a great place to start.

 

👉 Watch the full episode of Outside Insights with Jeff Ton

👉 Visit Jeff’s website to sign up for his free newsletter and to learn more about his book.

 

Until next time, friends,
Chris

 

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