Blakeley Vaughn spent 25 years at Sephora. Started on the floor, ended in a VP seat. Moved from Eugene, Oregon to Hollywood Boulevard to Madison Avenue to Atlanta. And somewhere in the middle of all of that, sitting alone on a park bench near the Met in Central Park, she almost threw the whole thing in.

In this episode, Blakeley and I dig into what it actually costs to climb a ladder when you're outsourcing your worthiness to the people above you, why friction is not the enemy of a good life but often the very thing that saves it, how building intentional community in a new city is the cheat code nobody talks about, and what it looks like to walk away from something you love on your own terms and ask, how good can it get from here?

Blakeley also shares the question that has followed her through every season, every role, and every hard conversation she's had to have. What is it you're really trying to do? It sounds simple. But depending on who's asking and how they're asking it, it will either cut you open or set you free.

She's now out of Sephora, fully energized, and ready to play with her Legos. And honestly, the world should be paying attention.

So here's what I want to leave you with. You've been working hard, climbing, building, achieving. But when's the last time you stopped long enough to ask yourself, what is it I'm really trying to do here? And were you brave enough to actually sit with the answer?

Stephen Proctor is an artist of light. He flies drones over glaciers in New Zealand, projects forests onto the walls of the Washington National Cathedral, and lives in a cabin in the Pacific Northwest woods that he named Rivendell. He got in trouble as a kid for shining a laser pointer in church. He now gets paid to illuminate churches. He'll tell you eight-year-old Stephen is absolutely losing his mind.

In this episode, Stephen and I dig into what it looks like to leave a creative mecca before it turns you cynical, why re-enchantment is the most important thing artists can offer a disenchanted world, what it cost him to work behind the scenes with people the world puts on pedestals, and why slowing down is not just an artistic choice but a philosophy of life.

Stephen also shares the three questions that changed everything for him. One from a mentor in New Zealand who asked what it would look like to put a single photograph on a screen and just let it breathe for an entire song. One from a friend sitting in a hot tub under the stars in California asking what it would look like to flip the model and create something entirely his own. And one about how you take your coffee that quietly started it all.

He closes by reading from his late Uncle Steve's worn paperback copy of The Fellowship of the Ring. And honestly, there was no better way to end it.

So here's the question I want to leave you with. You're busy, you're moving, you're consuming, you're producing. But when's the last time you just sat still long enough to let something beautiful actually do something to you?

• Book: Wild Wonder: What Nature Teaches Us About Slowing Down and Living Well — available on Amazon
• Company: Illuminate (Stephen's creative company)
• Instagram: @stephenproctor

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
• Book Page: www.callimurray.com/book
• The Brunswick: Available on Amazon, Barnes & Noble, Target, and Bookshop.org
• Instagram: calliemurray

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
• Website: www.jeremycowart.com
• Instagram: @jeremycowart
• X (Twitter): @jeremycowart

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

Instagram

Change Your Brain Foundation

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
• Website: www.jeremycowart.com
• Instagram: @jeremycowart
• X (Twitter): @jeremycowart

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 

Company

Book - Design Your Good Life

Book Video 

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

Instagram

Facebook

LinkedIn

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

Long Haul Leader

Newsletter

Instagram

LinkedIn

YouTube

TikTok

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 

Instagram

TikTok

YouTube

X (Twitter)