Callie Murray is not a clean LinkedIn narrative. She'll tell you that herself. She's got an HR company, a historical fiction novel just released, and a family that went from three kids to seven overnight when she and her husband David finalized the adoption of a sibling group of four through foster care. All in the same season. All at the same time. And somehow she still showed up for a TV interview before this podcast.

In this episode, Callie and I dig into what it actually costs to create something deeply personal and hand it to the world to rate with stars, why balance is a myth but order is everything, what it looked like to torpedo your entire carefully arranged life in the most beautiful way possible, and why a book launch party feels unfair when your friends are quietly surviving things nobody ever throws a party for.

Callie also shares the question her late father-in-law Bill used to ask that drove her absolutely crazy. And now she uses it on her own kids. What's the worst that could happen? Not to scare you. To free you.

So here's what I want to leave you with. There's something you've been wanting to try. Something that doesn't fit neatly into your LinkedIn bio or make sense to anyone at a dinner party. What if you just asked yourself, what's the worst that could happen? And actually followed the thread all the way to the end?

Social Links:

 * Website: www.callimurray.com [http://www.callimurray.com/]
 * Book Page: www.callimurray.com/book [http://www.callimurray.com/book]
 * The Brunswick: Available on Amazon, Barnes & Noble, Target, and Bookshop.org
 * Instagram: calliemurray [https://www.instagram.com/calliemurray/]

Episode 19 What's the Worst That Could Happen? A conversation with Callie Murray

Jeremy Cowart is one of the most celebrated photographers and creative minds alive. He's also genuinely terrified about where AI is headed. And that tension, being all in on something that scares you, turns out to be one of the most honest things you'll hear a creative say out loud in 2026.

In this episode, Jeremy and I dig into what it means to be an artist in the age of artificial intelligence, why EQ is becoming the most valuable skill on the planet as IQ gets cheaper by the minute, and how Jeremy built a tool called Humathy that starts with one simple question. How are you really? What happened next was thousands of people ugly crying, screenshotting it, sending it to their Bible studies and community groups, and a 96-year-old woman saying it was the best gift she'd ever been given.

Jeremy also shares the question his friend Jimmy asked him 25 years ago that changed everything. Five words. Why don't you do it tomorrow? He quit his job the next day and hasn't looked back since.

So here's what I want to leave you with. There's a question sitting somewhere in the back of your mind right now, something you've been circling, something you keep almost doing. What if somebody who loved you leaned across the table and asked you, why don't you just do it tomorrow? What would your answer be?

Social Links:

 * Humathy: www.humathy.com [http://www.humathy.com/]
 * Website: www.jeremycowart.com [http://www.jeremycowart.com/]
 * Instagram: @jeremycowart
 * X (Twitter): @jeremycowart

Episode 18 Why Don't You Do It Tomorrow? A conversation with Jeremy Cowart

Jason Wahler grew up in Southern California, became a household name on Laguna Beach and The Hills, fought a very public battle with addiction, and somewhere in the middle of all of it found the thing that actually mattered. A pillow fight with his kids on a random Tuesday night. Crying laughing. Nobody watching. Nowhere else to be.

In this episode, Jason and I dig into what it looks like to rebuild an identity after losing one, why the most influential experts are often the ones with the most lived experience, how comparison quietly destroys contentment, and why the people at the top of the mountain so often say they'd change everything.

Jason also shares the four questions he asks his kids every single night that turned into a 30-minute conversation with his eight-year-old daughter about friendship, heartbreak, and what it means to have a safe place to land. And the question that he now gives anyone who's wondering if something in their life has too much power over them. It's simple. It's just six words. And it works on everything.

So here's what I want to leave you with. You're chasing something right now. Maybe something big. But when's the last time you stopped and honestly asked yourself, is this actually adding to my life? Or have I just been too busy moving to notice it's been subtracting all along?

Find Jason:

www.jasonwahler.com [http://www.jasonwahler.com/]

Instagram [https://www.instagram.com/jasonwahler/]

Change Your Brain Foundation [https://www.changeyourbrain.org/]

Episode 17: What If Your Greatest Deficit Became Your Greatest Asset? A conversation with Jason Wahler

Charles Lee arrived in the US at five years old with very little English, moved to Koreatown in Los Angeles, watched his parents build a restaurant that became an institution and cost them their marriage, dropped out of college twice, and somehow ended up advising Toyota, Google, and Sequoia. He'll be the first to tell you he still doesn't feel like he's arrived. And that honesty is exactly what makes this conversation worth your time.

In this episode, Charles and I dig into what it actually means to design a life on purpose instead of just letting one happen to you, why the thing you're best at is usually the thing you take most for granted, how to move from a proof of concept to a proof of value, and why the most dangerous gap in most leaders' lives is the distance between how creative they are at work and how present they are at home.

Charles also shares the question a younger friend asked him over dinner in Atlanta that quietly restructured everything. It was piercing enough that I didn't want him to finish it. And I'm pretty sure it's going to do the same thing to you.

His new book, Design Your Good Life, is out now and it might be the most holistic leadership and life framework I've come across in years.

So here's what I want to leave you with. You're giving your best thinking, your most creative energy, and your sharpest attention to your clients and your company every single week. But when's the last time the people at home got that version of you?

Find Charles:

Website  [https://www.charlestlee.com/design-your-good-life-book-landing-page]

Company [https://ideation.com/assets/index.html]

Book - Design Your Good Life [https://www.charlestlee.com/design-your-good-life-book-landing-page]

Book Video  [https://www.youtube.com/watch?v=3ZjBx_e-2yQ]

Episode 16:What If You've Been Designing Someone Else's Good Life? A conversation with Charles Lee

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!) 

YouTube [https://www.youtube.com/@mattchenard]

Instagram [https://www.instagram.com/mattchenard/]

Facebook [https://www.facebook.com/matthew.chenard/]

LinkedIn [https://www.linkedin.com/in/matthew-chenard-3a51541a0/]

Episode 15: What If the Mountain Was Never About the Summit? A conversation with Matt Chenard

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: 

Website [https://www.chrisducker.com/]

Long Haul Leader [http://www.longhaulleader.com/]

Newsletter [https://www.chrisducker.com/]

Instagram [https://www.instagram.com/chrisducker/]

LinkedIn [https://www.linkedin.com/in/chrisducker/]

YouTube [https://www.youtube.com/user/chrisducker]

TikTok [https://www.tiktok.com/@chrisduckerofficial]

Episode 14: What Does This Make Possible? A conversation with Chris Ducker

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  [https://www.fasterfreedom.com/]

Instagram [https://www.instagram.com/samfasterfreedom]

TikTok [https://www.tiktok.com/@samfasterfreedom]

YouTube [https://www.youtube.com/samfasterfreedom]

X (Twitter) [https://x.com/fasterfreedom]

 Episode 13: They Said Don't Mix Business and Friends. He Ignored That. A conversation with Sam Primm.

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  [https://mikekim.com/]

Instagram  [https://www.instagram.com/mikekim/]

YouTube [https://www.youtube.com/@mikekim]

Newsletter [https://mikekim.com/newsletter]

Book [https://youarethebrandbook.com/]

Episode 12:  Success Cost Me Everything I Was Proud Of A conversation with Mike Kim

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 [https://www.instagram.com/nigeldarius/] 

Website  [https://nigeldarius.com/]

Book  [https://www.amazon.com/Say-Shalom-Cultivate-Curiosity-Connection/dp/1400351693]

Episode 11: The Cost of Becoming A conversation with Nigel Darius 

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  [https://www.instagram.com/andrewaverso/]

Website [https://averso.co/]

Episode 10: How Do You Reinvent Yourself? With Andrew Averso

One Great Question is a Curiosity podcast exploring leadership, decision-making, and human behavior through meaningful conversations. Each episode begins with a single question designed to challenge assumptions, spark insight, and help leaders think more clearly about people, work, and life.

Carl Lubbe

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