NYT Bestselling author Chip Leighton left a six-figure corporate career in his 50s to become a creator — and his kids wrote the foreword to his new book roasting him for it. This is that conversation.Chip is back on Happiness Sold Separately with Jason Hensley to talk about "Dad, Could You Not?: A Dad's Guide to Being Less Cringy" — but this goes well beyond dad jokes.They get into the real stuff: what humor does for our kids, the cost of betting on yourself when everything is safe, why letting go is the hardest part of parenting, and the moment that line — hold on loosely, but don't let go — changes everything.Plus: the Dad Meter Quiz. Are you Basic, Mid, or Extra?This is Happiness Sold Separately — a show about what it means to be human, the joy of it, and the cost of it. New episodes every Monday.📖 "Dad, Could You Not?" — available wherever books are sold📱 @theleightonshow | theleightonshow.com🎙️ Hosted by Jason Hensley | McCosh Films📱 @mccoshfilms🎧 Spotify · Apple Podcasts · All major platforms▶️ youtube.com/@mccoshfilms

There’s a quiet shift happening—and it’s not showing up in headlines, it’s showing up in how kids handle pressure, failure, and reality.

In this episode, Jason talks with MLB columnist Ken Davidoff and pediatrician Dr. Harley Rotbart about what youth sports used to teach—and what’s being lost. They get into entitlement, participation trophies, parental pressure, and the emotional consequences of removing failure from the equation.

This isn’t nostalgia.

It’s a real look at what happens when kids aren’t prepared for the world they’re walking into.

If you care about raising grounded, resilient humans… this conversation matters.

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Question: Are we protecting kids too much… or preparing them too little?

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She didn’t expect to end up there. What started as a way to survive in Los Angeles turned into something much heavier—something that changed how she saw herself, relationships, and the world. In this episode, Kendra Bates shares her journey from OnlyFans to Suddenly Amish, and the internal shift that forced her to walk away from everything she thought she wanted.

This is a raw conversation about identity, consequence, faith, and rebuilding your life when you realize you’ve gone too far down the wrong path. If you’ve ever made a decision just to get through a moment—and then had to live with it—this one will hit.

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Have a story you’ve never told? Send us an anonymous video confession.

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Most men think they’re doing everything right — working hard, providing, showing up. But what if that’s exactly where things start to break down? In this episode, Jason sits down with leadership coach Mitchell Osmond to unpack the silent crisis facing men today. From emotional disconnection to identity loss, this conversation reveals why so many marriages fail quietly and what it actually takes to rebuild connection at home without sacrificing success in the world. This is a raw look at masculinity, fatherhood, and the cost of getting it wrong.

Watch on YouTube: https://youtube.com/@mccoshfilms?si=DV9VCqBCVKA0YajD
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What’s something in your life that’s slowly slipping… and you haven’t faced yet?

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Abby Johnson has shared her story publicly for years—but this conversation goes deeper.

In this episode, we explore what’s happening inside abortion clinics today through the eyes of former workers—many of whom are leaving with lasting psychological trauma. Some stories are so serious that attorneys had to be consulted before they could even be shared.

This isn’t about headlines or politics. It’s about what people are actually experiencing, the emotional cost that lingers long after decisions are made, and what happens when truth becomes impossible to ignore.

Can you live with a decision you can’t undo?

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What happens when the life everyone admires… isn’t actually the life you’re meant to live?

Jonathan Cave spent years climbing toward what most people would call success — a respected legal career and a clear path to senior partnership.

From the outside, everything looked perfect.

But inside, something didn’t feel right.

In this episode of Happiness Sold Separately, Jonathan shares the moment he realized the life he had built no longer aligned with who he truly was — and the courageous decision to walk away from it.

Jason and Jonathan explore the hidden fears that shape our decisions, the emotional conditioning many of us carry from childhood, and why so many high-achieving people quietly struggle with imposter syndrome.

Jonathan explains his philosophy of Dare to Become, a powerful framework that challenges people to stop chasing external validation and start understanding themselves from the inside out.

This conversation dives into identity, emotional resilience, leadership, authenticity, and the courage it takes to become who you truly are.

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Your support helps us continue producing meaningful conversations that explore the emotional cost of being human.

Stay curious, stay connected, and keep the conversation going.

Have you ever realized the life you built wasn’t actually the life you wanted?

What helped you change direction?

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What if technology allowed you to talk to someone you lost years ago?

In this episode of Happiness Sold Separately, Jason sits down with entrepreneur Miles Spencer, founder of Reflecta, an AI platform designed to preserve a person’s memories, voice, and personality so future generations can interact with them long after they’re gone.

The concept is already sparking strong reactions. Some people believe this technology represents the future of family storytelling and legacy preservation. Others believe it crosses a moral boundary.

Miles shares the emotional story of speaking to his own father again through the platform, how the system builds a digital “reflection” using voice recordings and stories, and why families are beginning to use AI to preserve generational wisdom before it disappears.

The conversation explores deeper questions about memory, grief, and humanity. Can artificial intelligence truly represent a person who has passed away? Are we preserving legacy or simulating life?

This episode explores the intersection of technology, storytelling, and the human desire to hold onto the voices of those we love.

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At 18, Rob Scheer aged out of foster care with nothing but a trash bag and nowhere to go. Homeless and alone, he slept under bridges, hid in libraries at night, and still managed to graduate high school.

Decades later, he would turn that pain into purpose by founding Comfort Cases, an international nonprofit providing backpacks filled with essentials to children entering foster care — because dignity matters, especially in moments of crisis.

In this powerful episode, Rob shares the reality behind foster care myths, why so many former foster youth experience homelessness, how faith sustained him, and what it means to transform suffering into service. This conversation is both heartbreaking and hopeful, challenging listeners to rethink compassion, responsibility, and the role each of us plays in caring for the most vulnerable.

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