One Great Question

Matt Chenard lost $1.2 million dollars, his wife's nursing job, their life savings, and nearly his health. And he'll tell you straight up, it was the best thing that ever happened to him. Not because he's a masochist. Because it was the moment he finally stopped confusing a good thing for the ultimate thing.

In this episode, Matt and I dig into what it actually means to build a life around mission instead of achievement, why your habits are either deposits or withdrawals whether you make them consciously or not, how a penguin walking toward a mountain alone went viral for a reason, and why the most dangerous version of success is the one that quietly becomes your identity.

Matt also shares the one question that has restructured every major decision in his life, and it's only three letters. Why. Not once. Over and over again, until the real answer surfaces.

Oh, and somewhere in all of this he's also sitting in a frozen tub with an ax. In winter. In Canada. On purpose. And it might be the most brilliant piece of content strategy I've ever seen.

So here's what I want to leave you with. You're building something. Maybe something significant. But when's the last time you stopped long enough to ask yourself, if this thing disappeared tomorrow, would you still know exactly who you are?

Find Matt: (If he is not cold plunging!) 

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Chris Ducker built companies with nearly 600 employees, hit his first million dollar year, and was completely done. Not celebrating. Done. And then he did it again in 2021, this time landing in anxiety, depression, and phase three adrenal failure with cortisol completely flatlined. The long way back didn't start in a boardroom. It started with an hour a day in the woods, no AirPods, no podcast, no agenda.

In this episode, Chris and I dig into what it actually costs to build something significant, why letting go is the skill nobody teaches entrepreneurs, the difference between motion and momentum, and why the most successful people you'll ever meet all have one thing in common, a stillness practice that has nothing to do with work.

Chris also shares the question his mentor Dan Miller asked him that quietly restructured everything. Four words. What would this make possible? Simple enough to dismiss. Powerful enough to change the trajectory of his life twice.

Oh, and somewhere in the middle of all of this, he became a birder. Genuinely. And it might be the wisest thing he's ever done.

So here's what I want you to sit with. You're busy, you're building, and you're probably pretty good at it. But when's the last time you walked into something that had nothing to do with your output, your brand, or your bottom line and just let yourself be fully there?

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Most people were told the same thing growing up. Keep work and friendship separate. Don't mix business and pleasure. Play it safe. Sam Primm heard all of that and quietly decided to do the opposite.

Sam has 3.5 million followers, 2000 real estate deals, and a team of 55 people, about 15 of whom he's known since elementary school. His business partner Lucas has been his best friend for 25 years. They've painted houses for beer money, got into bar fights in college, and now they run a real estate and education company together. Eight-year-old Sam would lose his mind.

In this episode, we dig into what it actually takes to build a business with the people you love, why culture beats credentials every time you hire, how to stop "shoulding" on yourself and start asking better questions, and why the thing you keep putting off is probably exactly what you need to do next.

Sam's also one of the most genuinely generous people I've come across online, and the conversation proves it.

So here's the question I want to leave you with. You've been told your whole life to keep it professional and keep your distance. But what if the people who already know you, trust you, and would run through a wall for you are exactly the team you've been looking for?

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Most people chase success without ever asking what it's actually going to cost them. Mike Kim did the work, wrote the books, built the brand, and got close enough to the mountain to realize he was climbing the wrong one.

In this episode, Mike and I dig into what it really takes to become who you're meant to be, and why the price of that journey is almost always your pride. We talk about why consistency beats talent every single time, why work-life balance is a mythology we need to stop chasing, and why AI being the Ozempic of thinking might be the most important sentence you hear this week.

Mike also shares the question a mentor asked him over a meal that quietly changed the whole trajectory. Not a big dramatic moment. Just one question. That's usually how it goes.

So here's what I want you to sit with after this one. You've been working hard, staying consistent, checking the boxes. But when's the last time you stopped long enough to ask yourself if you even want the life at the top of the mountain you're climbing?

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Hey friends, we are back with another episode of One Great Question, and this one went somewhere I didn't expect, which is honestly my favorite kind of conversation.

Nigel Darius is one of those rare humans who is an author, keynote speaker, spoken word artist, and creative director, but more than any of those titles, he's just one of the best hangs you'll ever have. He grew up poor in rural West Virginia, and has since stood on stages in front of thousands, written books with Thomas Nelson, and built a platform on a single stubborn belief: there is hope for humanity.

But the road between those two places? Not a highlight reel. Think nine months without work, busing tables at a Michelin star restaurant, losing friendships, and a genuinely painful reckoning with what he actually believed about himself deep down.

We get into the mirror principle and why you literally cannot obtain what you're not yet aligned with, why psychological safety is the number one driver of healthy culture, what it actually looks like to signal safety to someone who thinks nothing like you, and why the Hebrew word shalom cannot belong to just one person and still mean anything.

Nigel also shares the question a friend asked him over a meal that quietly restructured everything. You'll know it when you hear it.

This is the kind of conversation that reminds you why dialogue still matters. And in 2026, I think we need that reminder more than ever.

New Book: We Say Shalom: 40 Words to Cultivate Curiosity and Connection is available now.

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What if the most powerful thing you could do for your career wasn't a strategy, it was a question?

In Episode 10 of One Great Question, Carl sits down with Andrew Averso, a multi-disciplinary creative who has reinvented himself across music, fashion, brand identity, and now his own creative house, Averso Co. What unfolds is a raw, honest conversation about the real cost of "success," why there's never a perfect time to start over, and what it actually looks like to bet on yourself when the bottom falls out.

Andrew talks about trading too much time and self-worth for career accolades, the anxiety that shadows creative people, and the single question that changed everything for him: Why? Carl and Andrew explore what it means to be present, how shame pulls us backward while anxiety pushes us forward, and why a strong identity isn't a luxury. It's the difference between your best idea seeing the light of day or going to the grave with you.

This one's for anyone who's ever felt the itch to reinvent themselves but couldn't find the courage to start.

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This final episode answers a practical question:  Now what?

After a full season of exploring curiosity and leadership, this conversation zooms out to look at the end goal. Not abstract philosophy, but real life.  Most people spend the majority of their waking hours at work.  If that time is consistently  confusing, draining, or joyless, something is broken.

In this episode, we connect all seven Curiosity Tools into a single, usable system. Purpose alignment. Clear expectations. Healthy conflict. Clear language. Idea implementation. People development. Self leadership. Not as isolated concepts, but as a set of building blocks that work together.

The result is simple but ambitious: less anxiety, better relationships, stronger teams, and more sustainable results. This is about doing the work and doing the people side of work well, at the same time.

The leadership industry is worth hundreds of billions of dollars, yet most leaders still feel unsure, lonely, and overwhelmed. That disconnect is not accidental.

In this episode, we challenge the idea that leadership is complex, mysterious, or reserved for experts with answers. Using stories from kitchens, soccer fields, bookstores, and boardrooms, we break leadership down into something far more practical and human.

Leadership is attention to the right problem.
It is an intention around a small set of possible solutions.
It is a commitment to experiment, learn, and stay with the work long enough to get a real result.

This conversation reframes leadership as a lived practice, learned in real time with real people, not a theory mastered in isolation. If you are tired of leadership advice that sounds impressive but changes nothing, this episode offers a simpler, more grounded way forward.

Most leaders think profit comes from speed. This episode argues the opposite.

In this conversation, we unpack a simple but demanding idea: the real profit is found in the pause. When leaders slow down long enough to ask what is unclear, anxiety drops and performance improves. When they do not, lazy language creates confusion, scattered effort, and quiet burnout.

Through stories of broken friendships, difficult endings, missed expectations, and everyday workplace moments, this episode shows how a lack of clarity creates open loops that drain energy for years. We explore why people confuse kindness with comfort, why brutal honesty is often lazy honesty, and how clear language sets boundaries without tearing people down.

This is an episode about leadership, relationships, and responsibility. If you want better results, healthier teams, and fewer unresolved tensions, it starts with slowing down and choosing clarity.

Most companies do not have a people problem. They have an orientation problem.

In this episode, we unpack why smart, capable people feel lost, anxious, and overwhelmed at work, even in healthy organizations. The issue is not motivation or talent. It is a lack of clarity around where someone is in the process and what comes next.

We explore why growth creates chaos, why chaos creates anxiety, and how leaders unintentionally make things worse by telling people to “figure it out.” Using the simple but powerful People Development Square, we break down how real training actually works, from observing to partial ownership to full responsibility, to teaching others.

If you have ever onboarded someone and assumed they would catch on, or if you have ever been afraid to admit you were lost, this episode gives you language, structure, and a shared map. Clarity does not slow teams down. It gives them a way forward.