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Hey friends, this is Jessica and Will from WorldTowning. You’re listening to the podcast that shares the highs, the lows, and the “what the heck just happened” of our decade-long full-time travel lifestyle and how it has changed us. On The WHY Matters, we dig deep into the WHY behind our choices and the positive results they leave. If you are ready to spread your wings, have a laugh, and take the insights of full-time travelers into your everyday life, then this podcast is for you.
55 Episodes
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Send us a text What would you do for a memory? Despite battling tendonitis, I reflect on my memories and the sacrifices I'm willing to make for them. I open up about my struggles with perfectionism, the physical pain of my injury, and my deep desire to prioritize experiences over material possessions. As I prepare to rejoin the hike, I hope to inspire you to consider your own "whys" and the lengths you would go to create meaningful memories with your loved ones. Welcome to 'The Why Matter...
Send us a text Are we letting Largo hike the AT Trail alone? Largo recently asked if we would allow him to finish the trail alone if Jessica couldn't continue. Life is full of uncertainties, and if Jessica is unable to finish, we would permit Largo to continue under specific guidelines. As he grows older, he needs less of our assistance and more opportunities to navigate life independently. Allowing him to experience this journey will help him become wiser, while we remain available to supp...
Send us a text Trigger Warning: We will discuss about sexual abuse. This may be triggering for you. We respect your decision to skip this episode. Listen again when we are back to our regular programming. “The healing begins, but it doesn't happen immediately.” One in six men experiences sexual abuse or assault. People do not see the aftermath of the trauma; many hide it, and it causes them to crumble. You have to understand that despite seeking therapy, even for years, the negative...
Send a text In this episode of The WHY Matters Podcast, we sit down in Paris with our longtime French teacher, Camille of Artful French, to talk about what it really takes to learn a language. From awkward yoga classes and repeating “je ne parle pas français,” to raising bilingual kids and questioning whether apps like Duolingo are enough, this conversation is honest, funny, and practical. We unpack why immersion matters, whether you’re ever too old to learn, the difference between understand...
Send a text In this episode of The WHY Matters Podcast, Jessica and Will officially welcome themselves into 2026, even if it’s mid-January and last year felt like it had 13 months. After a heavy season of grief, transition, and unexpected life pivots, they shift the conversation toward something lighter but still deeply intentional: goals. They reflect honestly on what it means to set goals in a season of uncertainty. With one child launching into university, another stepping fully into adult...
Send us a text In this episode of The WHY Matters Podcast, Jessica and Will share an honest, unfiltered conversation about grief in real time. After the loss of Jessica’s closest friend of 31 years, Doug, they explore what grief truly looks like — messy, isolating, and unpredictable. Jessica opens up about the anger, guilt, numbness, and exhaustion that come with loss, the pressure to keep showing up, and why sharing grief while you’re in it matters. This episode isn’t about fixing grief, but...
Send us a text PATREON https://www.patreon.com/worldtowning If you would like to support us in a greater capacity where you can snag some cool swag, plus join us for monthly LIVE chats, and get huge discounts on future group trips. Thank you! GROUP TRIPS https://worldtowningvoyages.com/ Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is building bridges between cultures, fueling personal development, and expanding hearts and...
Send us a text In this episode of The WHY Matters Podcast, we sit down with Jamless and Green Bean, a daughter–mother duo who took resilience to the extreme by attempting a thru-hike of the Appalachian Trail together—and learned that endurance isn’t just about pushing forward, but knowing when to pause. They share the unfiltered reality of starting a massive journey at two very different stages of life: Jamless, young, driven, and physically capable, and Green Bean, experienced, determined, a...
Send us a text Before we begin, we want to share something important. This episode originally aired when our close friend Doug was very much alive, sharing his perspective with the warmth and curiosity that defined him. At the time, none of us knew this conversation would become a memory we would one day hold so dearly. Doug is no longer with us, and that still feels unreal. He had a rare way of making people feel seen, bringing lightness even to heavy conversations, and reminding us that lif...
Send us a text In this episode of The WHY Matters Podcast, we unpack a lesson they learned the hard way - that sometimes, resilience isn’t about pushing harder, it’s about stopping. From hemorrhoid surgery to burnout on the road, they get real about the hidden cost of “sucking it up” and why our culture glorifies being busy. Through stories from their sailing years, cross-country hikes, and even parenting two ambitious kids, they explore the fine line between perseverance and self-betra...
Send us a text In this episode of The WHY Matters Podcast, Will and I unpack one of the most asked questions we get as full-time traveling parents — how on earth did our kids become trilingual? What started as a simple desire to expose our children to different cultures turned into a years-long journey through French immersion programs, homeschooling abroad, and more than a few unforgettable (and painful) teacher experiences. From Boston to Costa Rica to France, we share the real story behind...
Send us a text In this episode of The WHY Matters Podcast, Will and I dive into a topic close to our hearts - celebrating homeschooling milestones. It all started with a post from a mom whose son’s homeschool graduation went unnoticed. That moment opened a deeper conversation about how nontraditional learners - homeschoolers, deserve to be recognized just as much as traditional students. From Avalon’s graduation in the middle of the Caribbean to Largo’s upcoming celebration, we share ho...
Send us a text In this episode of The WHY Matters Podcast, Will and I open up about what aging has been teaching us - and why waiting for “someday” to chase big adventures is a mistake. A tough volcano trek in Guatemala showed us firsthand that our bodies don’t bounce back like they did in our 30s. That wake-up call, paired with the wisdom (and regrets) of older travelers we’ve met along the way, pushed us to make one of our biggest decisions yet - attempting a thru-hike of the Appalachian Tr...
Send us a text In this episode of The WHY Matters Podcast, Will and I share what it was really like to spend five months living in one Holiday Inn room - not on vacation, but as a family navigating work, school, and life together in a tiny space. From cooking without a kitchen to dealing with noisy neighbors and even “Weed Alley,” we open up about the challenges, the laughs, and the lessons we’ll never forget. We get real about: @01:08 Why a Hotel – How we ended up in a Holiday Inn for ...
Send us a text In this episode of The WHY Matters Podcast, Will and I get real about what it means to live like “working retirees” in our 40s and 50s while raising kids and traveling full time. Most people wait until their 60s to start chasing bucket-list adventures, but we’ve chosen to do it now — blending work, parenting, and travel into one messy, magical, and challenging lifestyle. From crossing oceans on a sailboat to hiking the Andes and even through-hiking the Appalachian Trail, we’ve ...
Send us a text In this episode of The WHY Matters Podcast, Will and I open up about the stories behind our tattoos and the meaning they hold for us. What might look like simple body art is actually a reflection of family, love, travel, and identity. From my first strawberry tattoo at 17 to Will’s dolphins for our kids, and the travel-inspired sleeve I’ve been building along the way, each one carries a piece of our journey. For us, tattoos aren’t just decoration, they’re a living journ...
Send us a text In this episode of The WHY Matters Podcast, we dive into Largo’s journey of questioning a childhood dream and discovering a new path forward. From his earliest memories, he wanted to be a pilot - but when reality didn’t match the dream, he made the bold choice to step away and rethink everything. Through honest reflection, Largo shares how he moved from disappointment to curiosity, and how critical thinking became his compass for navigating big life decisions. This is a s...
Send us a text In this episode of The WHY Matters Podcast, we share the story of how a dusty, empty building in rural Cambodia became a bright and welcoming library. Jessica, Largo and Will, talk about the two-year journey - raising money, carrying six suitcases of books, painting in the heat, and working side by side with kids, volunteers, and the local community. From replacing the roof to adding shelves, beanbags, and fairy lights, this project was about more than fixing up a space -...
Send us a text In this episode of The WHY Matters Podcast, we lace up our boots for a deeply human look into long-distance hiking, family bonds, and personal transformation. Jessica and her son Largo, share our experience hiking over 2,000 miles of the Appalachian Trail, all while juggling remote schooling, teenage growth, and the realities of life after a decade abroad. From trail names to trail magic, we dive into what it really means to strip away the noise of modern life and walk, literal...
Send us a text In this episode of The WHY Matters Podcast, Jessica and Will Serro open up about the untold realities of 10 years of full-time travel as a family, and what happens when the road doesn’t magically fix what’s going on inside. In a raw and insightful conversation originally aired on the Zero to Travel podcast with host Jason Moore, they explore how travel can both unravel and rebuild you. From mental health breakdowns to parenting teens across continents, from redefining “home” to...
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refreshing and inspiring! definitely give a listen <3