243. How to Raise More Free-Range, Confident, and Adventurous Kids
Family Brand: Take Back Your Family
Release Date: 11/28/2025
Family Brand: Take Back Your Family
This episode started the way some of our best conversations do — on a walk. Chris and Melissa talk about why the idea of “balance” often leaves families frustrated, exhausted, and feeling like they’re failing. Instead, they introduce a different lens that has brought them far more peace over the years: seasons of life. Every season affords certain opportunities. Every season also has real limitations. And neither are permanent. Chris shares a conversation he had with someone wrestling with a big opportunity — one that looked great on paper, but didn’t quite align with the season of...
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Couple’s Playbook: Getting on the Same Page for the Year Ahead It’s easy to start a new year with good intentions — and just as easy to lose them once life speeds back up. In this episode, Chris and Melissa talk about why so many couples want to be intentional but struggle to actually do it together. The issue isn’t desire. It’s structure. Most couples don’t need more motivation — they need a simple playbook that creates the right conversations. They kick things off with a lighthearted look at Chris fully embracing his cowboy era (yes, cowboy hats and horses included), which...
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Wanting to Believe: Re-Enrolling Each Other Into What’s Possible This episode came out of a conversation Chris had this week — and it hit him so clearly that he realized he and Melissa had never talked about it publicly before. They’ve shared openly about the hard seasons in their marriage. They’ve taught frameworks for having honest, productive conversations about what isn’t working. But in this episode, they talk about the missing piece that made all the difference when their marriage was at its lowest: They started talking about what they wanted to create — before there was any...
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Couple’s Playbook for 2026: Setting the Frequency for Your Year It’s that time of year when the Smith family pauses, reflects, and intentionally sets the tone for the year ahead. In this episode, Chris and Melissa walk through exactly how they approach vision boards, words (or frequencies) for the year, and why doing this work up front creates so much more ease as the year unfolds. While they share what this looks like in their own family, their hope is that it gives you practical inspiration you can adapt for yours — no matter what time of year you’re listening. They talk about why...
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The Power of Boredom: Learning to Live in the Present In this solo episode, Chris shares a personal experiment that quietly changed the way he experiences life. It started with a conversation around a Harvard study shared by Arthur Brooks — research suggesting that one of the biggest challenges we face today is that we never experience boredom. Every spare second is filled. Every pause is interrupted. And in the process, we’re losing something deeply important: the space to think, reflect, and be present. While celebrating his 20-year anniversary with Melissa in Spain, Chris decided to...
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You Are Firemen: Built to Lead, Built to Last This week’s episode is part reflection, part celebration, and part reminder. Chris and Melissa sit down to talk about two big milestones: the recent Family Brand Blitz and the five-year anniversary of The Family Brand Podcast. And instead of just sharing highlights, they unpack the deeper lessons that emerged — about consistency, leadership, and why families are far more capable than they often realize. They reflect on the power of bringing couples together in person at the Blitz, how every family — no matter the stage — is carrying...
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The Family Brand New Year’s Kickoff: A Tradition That Builds Culture Every year, right after Christmas — during those quiet, in-between days when no one quite knows what day it is — our family slows down and does something that has become one of our most meaningful traditions. We reflect. We celebrate. And we intentionally step into the new year together. In this solo episode, Melissa walks you through the Family Brand New Year’s Kickoff, a simple, free activity that hundreds of families download every year — and come back to again and again. This year’s version has been fully...
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As we head into a new year, Chris and Melissa wanted to revisit a conversation that has quietly shaped their family more than almost anything else: the power of language. This idea — that language creates — was one of the very first topics ever discussed on The Family Brand Podcast, and it’s still one of the most talked-about episodes to this day. Because once you see it, you can’t unsee it. In this episode, Chris explains why language is never neutral. The words we use are either rooted in possibility or anchored in limitation — and over time, they shape our beliefs, our behaviors,...
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Chief Reminding Officer: The Power of Repetition in Your Family If you’ve ever felt like a broken record as a parent — constantly reminding your kids (or yourself) of the same things over and over — this episode will make you feel a whole lot better. This week, Chris and Melissa talk about something they’ve been feeling in both their home and business lately: that quiet drift that happens when you stop doing the simple things that actually work. The routines that keep your house running. The systems that make your marriage stronger. The habits that help your family thrive. And the...
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Have you ever caught yourself saying “no” to your kids’ adventures out of pure instinct — only to wonder later if maybe the risk was worth it? In this episode, Chris and Melissa talk about how they’re learning to raise kids who are more confident, capable, and adventurous by saying yes a little more often. The idea started after Melissa read The Anxious Generation by Jonathan Haidt — a powerful book that explores how modern parenting and constant digital connection have created more anxious, less independent kids. Together, they reflect on how the shift from outdoor play to screens...
info_outlineHave you ever caught yourself saying “no” to your kids’ adventures out of pure instinct — only to wonder later if maybe the risk was worth it? In this episode, Chris and Melissa talk about how they’re learning to raise kids who are more confident, capable, and adventurous by saying yes a little more often.
The idea started after Melissa read The Anxious Generation by Jonathan Haidt — a powerful book that explores how modern parenting and constant digital connection have created more anxious, less independent kids. Together, they reflect on how the shift from outdoor play to screens has changed childhood, and what parents can do to reclaim freedom and resilience for their kids.
They share personal stories from their own family — like letting their teenage son navigate New York City solo, their kids exploring Paris and Croatia by themselves, and their 10-year-old’s first bike ride to school (which included a coyote sighting and a dog chase). Each story carries the same theme: that a little bit of risk, independence, and real-world adventure is not just okay — it’s essential.
Chris and Melissa also discuss how media consumption has shaped our fears, why the world may not actually be more dangerous than it used to be, and how giving kids appropriate autonomy builds courage and confidence. They tackle the smartphone dilemma too — why they’re rethinking when their kids get phones, and what it means to trade “connection” for constant anxiety.
This episode will inspire you to loosen the reins just a bit, trust your kids more, and rediscover the joy of letting them learn through life — not just lectures. As Chris puts it, “Adventure builds confidence. Confidence builds courage. And courage builds character.”
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Episode Minute By Minute:
- 00:00 – The inspiration behind today’s topic: The Anxious Generation
- 01:00 – Introducing the Family Brand Croatia Cruise (June 20–27!)
- 03:00 – Letting their 17-year-old explore New York City alone
- 05:00 – How independence builds confidence and perspective
- 06:00 – Kids navigating Paris, Croatia, and new cities on their own
- 08:00 – The 10-year-old’s first solo bike ride (and wild encounters)
- 10:00 – How small risks create big growth and resilience
- 11:00 – Is the world really more dangerous than it used to be?
- 12:00 – The role media plays in fueling parental anxiety
- 13:00 – What The Anxious Generation teaches about freedom vs. fear
- 15:00 – Revisiting your family’s smartphone rules
- 16:00 – Chris’s powerful analogy: “Would you pay for your child’s destruction?”
- 17:00 – The Harvard study on boredom and why it’s good for kids
- 18:00 – Rediscovering stillness and creative thought
- 19:00 – Building community around shared parenting values
- 20:00 – Changing the narrative: why “different” is good
- 21:00 – Rewriting your family’s agreements — it’s never too late
- 22:00 – Holiday reflections: gifts that inspire adventure, not anxiety