One Great Question

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?Find Chris: WebsiteLong Haul LeaderNewsletterInstagramLinkedInYouTubeTikTok

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?Website InstagramTikTokYouTubeX (Twitter)

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?Find Mike Kim:Website Instagram YouTubeNewsletterBook

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.Find Nigel Darius:Instagram  Website Book 

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.Instagram Website

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.

Burnout isn’t about working too hard, it’s about not knowing why your work matters.In this episode, we dive into the power of asking the right question: “Does my job matter?” is a lazy question, it seeks reassurance. “Why does my job matter?” is a demanding question, it creates clarity, responsibility, and real meaning.We’ll uncover how purpose shows up in everyday work, why money alone can’t fuel motivation, and how leaders often unintentionally disengage their teams by failing to link the smallest tasks to real-world impact. From freezing New England factories to flashy, but hollow—high-paying gigs in Las Vegas, we reveal how meaning is built, lost, and rebuilt.If you’re ready to see your work, and your team’s work through a purpose-driven lens, this episode will change the way you think about why you do what you do.

Most disappointment at work doesn’t start with bad intentions. It starts with unclear expectations.This episode explores why teams, relationships, and organizations fall apart when no one defines the rules of the game. Using stories from childhood playgrounds, leadership failures, and real workplace dynamics, we unpack how unclear wins, missing deadlines, and unspoken assumptions quietly turn into frustration, disappointment, and eventually resentment.This conversation introduces a simple but demanding framework for setting expectations well: define the win, make it measurable, check if it’s doable, match resources, and revisit the agreement as conditions change. Expectations are not contracts. They’re experiments.If you’ve ever felt blindsided, burned out, or quietly resentful at work, this episode will help you see why. More importantly, it will show you how to reset the game before everyone walks away.​​​​​​​​​​​​​​​​

Great ideas are easy to fall in love with. Turning them into something real is where most teams get stuck.This episode explores the quiet tension between vision and execution, and why so many promising ideas either die too quickly or exhaust the people responsible for making them happen. We unpack a simple but powerful shift: treating ideas as possibilities, not mandates, and separating who you are from what you propose.Through stories from leadership, songwriting, and real-world team dynamics, this conversation offers a clear framework for moving ideas from imagination to action without burning trust, energy, or morale. It’s about creating space where visionaries feel safe to share, implementers feel respected, and everyone knows what happens next.If you’ve ever left a meeting wondering whether an idea actually mattered, this one is for you. Listen in. Stay curious.​​​​​​​​​​​​​​​​

This episode sets the foundation for everything that follows.We start with a simple, uncomfortable question: why are we here? Not as a productivity exercise or a branding hook, but as an honest invitation into better conversations.Most questions are assumptions in disguise. Asking better questions changes how we work, lead, relate, and live. This podcast offers a framework built around seven core questions, not as a fixed doctrine, but as a flexible system. You can enter wherever you are and circle back as needed.This isn’t about curiosity, as cleverness, or sounding smart. It’s about creating space for conversations that feel alive, risky, and meaningful. The kind that might disrupt you. Or quietly change everything.​​​​​​​​​​​​​​​​

Most conflict is not caused by bad intentions. It happens when curiosity disappears.This episode explores a deceptively simple question that changes everything: When was the last time you asked a real question? From a surprising John Lennon and Yoko Ono story to a real-time conflict that forced us to change where we were filming mid-recording (haha), we examine how connection is built or broken in moments of tension.We talk about why winning often costs more than it gives, why great questions need the right room, and how conflict stops escalating when two people search for two yeses instead of one victory.This is not about clever techniques or power moves. It’s about presence, humility, and the courage to stay curious when it would be easier to shut down.Listen in if you want fewer battles and more understanding. Stay curious.​​​​​​​​​​​​​​​​