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Why slowing down, listening better, and taking the long way still matters

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

If this conversation resonates, forward it to a friend or colleague. Insight is meant to be shared. Quick reviews on your listening app go a long way, too.

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I had the opportunity to sit down with Sam Maddula, a founder whose career does not fit a clean headline. What stood out immediately wasn’t the size of the business he built, but the decisions he made along the way, and the ones he chose not to make.

This conversation isn’t about hacks or hypergrowth. It’s about judgment, timing, and the quiet moments when leaders realize the path forward isn’t obvious.

A Business Built in the Margins

Sam started his company in a highly specialized corner of healthcare, serving patients and physicians in situations where the stakes were high and the system rarely worked smoothly. Growth came, but not in the way business books describe it.

Instead of rapid expansion, Sam talks about constraints. About capacity. About learning when “yes” would eventually cost more than it was worth.

Those trade-offs shaped everything that followed.

When Success Starts Asking Questions

As the business matured, so did the weight of leadership. Responsibilities multiplied. Expectations rose. And life, as it does, introduced moments that forced Sam to reconsider what success actually required of him.

We talk about what happens when the role you created begins to demand more than you’re willing to give, and how hard it is to admit that out loud.

The Hardest Transition

One of the most compelling parts of our conversation centers on transition. Not just the professional mechanics of stepping away, but the emotional and identity shift that follows.

Sam shares what surprised him most about that period, what he underestimated, and what ultimately helped him move forward with clarity rather than regret.

The Core Question

Throughout the episode, one question keeps resurfacing: how do you build something meaningful without losing yourself in the process?

Sam doesn’t offer formulas. He offers perspective shaped by experience, and the humility that comes from learning in real time.

“You don’t really know what matters until you’re forced to choose.”

This episode is a thoughtful look at leadership, transition, and the decisions that define a career long after the titles change.

Click HERE to watch to the episode.

Until next time, friends,

Chris

If this conversation resonates, forward it to a founder or leader who might appreciate it. Insight is meant to be shared.

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I had the honor of hosting a long-time mentor and friend, Robert Larson, CPC. Bob’s journey is one I’ve followed since the start of my first business, and he even inspired my own early yoga practice by bringing his personal interests into the workplace.

The episode is less about business growth and more about personal resilience and the powerful difference between working on your business versus in it; and ultimately, working on yourself.

From Bicycle Messengers to Boutique Practice
Bob's career spans decades, starting when résumés were shuttled by bicycle messengers and a portable fax machine cost $4,500. He built a large, successful staffing firm. However, as the conversation reveals, he deliberately chose to downsize a few years ago.

He found that running a large operation meant working on the business. Downsizing allowed him to return to the craft, the hands-on work of interviewing and placement, and find fulfillment, proving that the work is more fulfilling.

The Catastrophic Gift of Life
Bob's most compelling story is about the massive health crisis he faced over 20 years ago that put him on life support, reshaping his outlook on life, work, and gratitude.

He discusses how his decades-long practices in silent meditation and Bikram (hot) yoga became his lifeline. When he woke up on a respirator, he used the machine's rhythm to perform Ujjayi breathing meditation. As his sister-in-law wisely noted, he "trained his entire life for these illnesses." Now, at 75, he embodies reinvention and acceptance, trading marathons for chair yoga, and viewing every physical challenge as a teaching moment.

The Core Takeaway: Find Your DNA
Life comes with no warranties or guarantees. Bob's advice on career and contentment is simple yet revolutionary: find what is in your DNA and what you love to do, and the money will follow. His perspective on career fulfillment, the necessity of personal practice, and the struggle to stay in the present moment is a powerful reminder that awareness is the practice, and coming back to stillness is the key to clarity.

"If a person does what they love, the money follows because they rise to the top of what they're doing." — Robert Larson, CPC

Listen to the Full Conversation

Don't miss Bob's incredible story of resilience and his profound advice on living an aware and grateful life.

Books, Websites, and Resources Mentioned

We always highlight the resources mentioned by our guests so you can follow their lead.

• Substack: You can follow Bob Larson's active daily blog and get a peek into his daily practice of gratitude and awareness
• A Book for Letting Go: Let Them by Mel Robbins
• The Business Essential: The E-Myth Revisited by Michael E. Gerber
• Career Assessments: The Kuder Career Assessment and Campbell Interest and Skill Survey

Until next time, friends,

Chris

If this conversation resonates, forward it to a friend or colleague. Insight is meant to be shared. Quick reviews on your listening app go a long way, too.