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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

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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

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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.

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Welcome back Marnie Stockman, Ed.D. and Nick Coniglio, authors of the phenomenal new book, The Business of You.

This episode provides a complete methodology for anyone doing the “right things” (good grades, internships, etc.) but still struggling to stand out or land the job they actually want. It's time to stop letting the world define your value and start defining it yourself.

The traditional career ladder is obsolete. We discuss why you must Run Your Life Like a Business, serving as your own CEO, Head of HR (identifying your core values), and Head of Marketing (crafting your personal brand).

We explore the essential difference between the old Credential Ladder (stacking titles) and the Value Ladder (generating value for others). Learn why you need a Personal Board of Advisors—specifically a Challenger—to push you.

Your competitive advantage is your Story. In a world of AI-scanned resumes, learn how to move from selling your story to genuinely sharing it. Finally, we cover the Power of Adaptability and why you must practice resilience using a pre-mortem to stress-test your plans before they fail.

“If you’re not intentionally taking care of what your persona is in the public, it will be done for you. People will make assumptions.”

Listen to Episode 67 for the full discussion.

Until next time, friends,

Chris

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I’ve wanted Ari Weinzweig on the show for a long time. If you don’t know Ari, he co-founded Zingerman’s in Ann Arbor and helped grow a single deli into a whole community of businesses including a bakehouse, coffee shop, candy store, ZingTrain, and more, without losing soul. That’s rare.

We cover a lot, but here are the big beats, human-sized:

From Dishes to Direction

Ari didn’t plan a career in food. He connected with great people, put in the work, and eventually discovered the power of writing a clear, story-based vision, not just a spreadsheet of goals.

It’s All One Life

Self-awareness isn’t a side project. If you’re pretending to be someone else at work, it shows. The real win is being the same person both on and off the clock.

Systems That Serve People

ZingTrain turned good habits into teachable tools: purposeful meetings, open-book rhythms, and change done with people (Bottom-Line Change).

Business as Art

What if every email, service moment, and decision is a brushstroke? Choose beauty on purpose, especially when it’s easier not to.

Dignity, Daily

Ari shared six practices that make workplace cultures feel different in the best way:

• Honor everyone’s humanity
• Be authentic (without acting out)
• Give people a meaningful say
• Start from positive beliefs
• Help folks reach their version of greatness (within your values)
• Work toward equity: pay, information, access, and support

Why This Matters Right Now

Uncertain times tempt leaders to tighten fists and shrink vision. Ari argues the opposite: tell a vivid story of where you’re going, build simple systems that help people win, and practice dignity, especially when you’re tired. That combination scales culture without hollowing it out.

Links & resources

• Listen to Episode #66 with Ari Weinzweig
• Zingerman’s Community of Businesses (deli, bakehouse, creamery, mail order, coffee, Roadhouse, candy, Cornman Farms, Miss Kim, food tours)
• ZingTrain training: visioning, service, open-book habits, Bottom-Line Change
• Ari’s books & pamphlets: A Lapsed Anarchist’s Guide series; The Art of Business; A Revolution of Dignity; Life Lessons I Learned fro

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This week on Outside Insights, I sat down with my good friend John Sanders, founder of Bridgeforce, to talk about what it really takes to build a business that endures.

John’s story isn’t about quick wins or flashy exits. Over the past 25 years, he and his partner have built a management consultancy serving global banks, credit unions, fintechs, and lenders — staying true to the values they set on day one.

The Leap of Faith

Bridgeforce began with a breakfast conversation, a bold “I’m in,” and a same-day resignation. No parachute. No safety net. Just conviction that failure was not an option.

That leap defined the next quarter-century of John’s life.

Lessons from the Journey

Throughout our conversation, John shared some hard-earned lessons:

• Every stage brings new challenges. Surviving the first three years was one kind of test. Scaling brought others. Even today, the obstacles evolve.
• Motion creates insight. You can’t steer a parked car. Progress requires movement, even when the path isn’t perfect.
• Culture matters. Bridgeforce was built on a simple plus/minus exercise: do more of what we admired in others, none of what we didn’t. That clarity still guides the company.
• Protect what you value. Whether it’s intellectual property, your people, or your principles, what matters to you will matter to others — and sometimes it must be defended.
• Strategic energy beats constant energy. You don’t need to win every race. You just need to run the right ones.

Leadership Through Crisis

We also talked about leading in uncertain times, including the pandemic. John’s approach was deeply personal: calling every employee, shouldering their worries, and reminding them they didn’t have to carry the weight alone.

That philosophy — let me worry for you — says a lot about the leader John has become.

What He’d Tell His 21-Year-Old Self

Relax. Sit in the pocket. Don’t rush.
And… buy Apple stock.

Recommended Reading

One of John’s all-time favorite books is Tuesdays with Morrie by Mitch Albom — a reminder that the most profound lessons on how to live often come from those nearing the end.

Connect with John

You can learn more about John and Bridgeforce at:
👉 Bridgeforce.com

In the end, John and I agreed that the true rewards in business and life are often the simplest: a good meal, a walk, and maybe a nap.

🎧 Listen to Episode 65 now
📩 Share this with someone who’s carrying too much alone — and could use a reminder that leadership means sharing the load.

Until next time, friends,
Chris

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How business coach Nikhil Paul helps companies grow by going narrow, not wide

Most business owners think scaling means reaching more people.
Nikhil Paul says it’s the opposite.

In this week’s Outside Insights, my longtime friend and small business growth coach shares why the fastest path to growth is going narrow, not wide—and how identifying your cult customer can transform your business.

Your cult customer is the one who:

• Pays you the most
• Forgives you when you mess up
• Loves your product so much they can’t stop talking about it

When you know exactly who they are—and build your business around them—you stop chasing everyone, and start leading someone.

We explore:

• What CrossFit, Costco, and Patagonia can teach us about niche obsession
• Why embracing your “weirdos” can turn a company into a movement
• The pen-and-paper exercise that reveals your cult customers in 10 minutes
• How doubling down on your core audience can let you break industry rules and still win

Along the way, Nikhil shares real-world stories—from Death Wish Coffee’s “too strong” gamble to Solé Bicycles’ pivot from exercise gear to lifestyle brand—that show how focus fuels profit, loyalty, and freedom.

If you’re trying to scale beyond $5M, reconnect with your company’s heart, or cut through the noise, this episode will give you the clarity—and courage—you’ve been looking for.

🎧 Listen to Episode 63 now
📩 Share this with a founder or leader who’s ready to grow by going narrow.

Until next time,
Chris

If this conversation resonates, forward it to a friend or colleague. Insight is meant to be shared.

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What would it take to step away from a life that looks successful — but no longer feels like your own?

In Episode 63 of Outside Insights, I talk with Rose and Glynn Willard — entrepreneurs, parents, adventurers, and creators of Reset Your Journey. After building a thriving fitness business and moving into their dream home, they made a radical decision: to sell everything, buy an RV, and travel full-time with their kids.

Their story offers an honest, vulnerable look at how to bridge the gap between the life you’re living and the life you truly desire.

This isn’t just a story about RV living — it’s about:

• Taking a “mini retirement” or earned pause to reset your priorities
• Building a financially sustainable life of freedom without sacrificing security
• Roadschooling and raising resilient kids outside the norm
• Embracing discomfort, minimalism, and the unknown
• Facing the challenges of reentry after living differently

We talk about everything from boondocking tips and mobile tech setups to how they sold their business — and why they sometimes question that decision. We explore how they protected their time, learned to slow down, and what they’d do differently if they started again.

Their journey holds lessons for anyone considering a sabbatical, navigating a career pivot, or wondering how to live with more intention — without losing everything they’ve worked for.

If you’ve ever asked yourself:

• Could I live more simply?
• What’s really keeping me stuck?
• Is now the time to make a leap?

Then this episode is for you.

🎧 Listen to Episode 63
🌐 Explore their blog + videos: https://www.resetyourjourney.com

Whether you’re dreaming of a slower pace or simply curious about what it takes to redefine success — this is the conversation you need to hear.

Until next time, friends,
Chris