The WHY Matters

Episod

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  #55 - Women’s Month: Travel, Courage & Alignment - The WHY Matters Podcast 24.03.2026 1j 18min

  Send us Fan Mail In this episode of Why Matters Podcast, we sit down with Karen for a powerful and deeply human conversation about reinvention, courage, and what it really means to choose a life that aligns with who you are becoming. Sparked by the idea that a “good life” isn’t always a fully expressed one, this episode explores how curiosity, discomfort, and the willingness to question everything can open the door to something more expansive. We talk candidly about walking away from a life t...
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  #54 - Women’s Month: Corporate Life to Full-Time Travel: Alignment Over Comfort - The WHY Matters Podcast 18.03.2026 1j 14min

  Send a text In this episode of The WHY Matters Podcast, Jessica and Will kick off International Women’s Month with a powerful conversation about reinvention, courage, and choosing a life that feels aligned. Their guest, LiAnne, shares how she walked away from a successful corporate career, sold everything she owned, and began traveling the world full-time with her daughter. What started as a search for something more after losing both of her parents became a complete life transformation...
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  #53 - Saying BYE to Trumper Friends | Who Gets a Seat at Your Table? 04.03.2026 56min

  Send a text In this episode of Why Matters Podcast, we dig into a heavy but necessary conversation about friendship, morality, and what it really means to choose values over comfort. Sparked by a viral declaration, “I don’t have one Trump-supporting friend and I never will,” this episode explores how political alignment has blurred into questions of humanity, equality, and harm, and why avoiding that reality comes at a personal cost. We talk candidly about why this isn’t about being morally s...
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  #52 - What Trumpers Need - The WHY Matters Podcast 25.02.2026 55min

  Send a text In this episode of Why Matters Podcast, we dig into a heavy but necessary conversation about therapy, trauma, and what it really means to live an authentic life. Sparked by the idea that unprocessed trauma doesn’t disappear, it recruits beliefs, identities, and enemies, this episode explores how pain that goes unexamined can quietly shape worldviews, relationships, and behavior. We talk candidly about why therapy isn’t about being “better” or morally superior, but about having too...
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  #51 - Why Learning a New Language Matters - The WHY Matters Podcast 18.02.2026 1j 5min

  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 as an adult. 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 betwee...
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  #50 - Our 2026 Goals - The WHY Matters Podcast 11.02.2026 40min

  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...
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  #49 - When Grief Takes Over - The WHY Matters Podcast 04.02.2026 1j 6min

  Send 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 ab...
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  #48 - 2025 Recap! - The WHY Matters Podcast 21.01.2026 1j

  Send 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 mi...
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  #47 - A Mother–Daughter Journey on the Appalachian Trail - The WHY Matters Podcast 14.01.2026 1j 41min

  Send 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, and ...
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  #46 – The Power of Meditation with Our Dear Friend Doug - A Tribute 07.01.2026 53min

  Send 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 life i...
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  #45 - Taking a Rest - The WHY Matters Podcast 12.11.2025 40min

  Send 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-betrayal...
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  #44 - Raising Trilingual Kids: The Real Cost, Chaos, and Magic of Multilingual Living 22.10.2025 1j 9min

  Send 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 ra...
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  #43 - Celebrating Homeschooling Milestones - The WHY Matters Podcast 08.10.2025 24min

  Send 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 how f...
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  #42 - The Wake-Up Call - Aging, Adventure, and Why We Can’t Wait - The WHY Matters Podcast 24.09.2025 37min

  Send 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 Trail...
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  #41 - Living in a Hotel - The WHY Matters Podcast 17.09.2025 38min

  Send 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 mon...
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  #40 - Living Our Retirement Dreams in Our 40s - The WHY Matters Podcast 10.09.2025 45min

  Send 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 had...
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  #39 - Why All The Tattoos - The WHY Matters Podcast 03.09.2025 56min

  Send 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 journal ...
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  #38 - The Pilot Who Pivoted - The WHY Matters Podcast 27.08.2025 48min

  Send 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 stor...
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  #37 - Building a Library in Cambodia with Largo Sueiro - The WHY Matters Podcast 19.08.2025 51min

  Send 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 - it...
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  #36 - Hiking the Appalachian Trail with Jessica & Largo - The WHY Matters Podcast 23.07.2025 1j 14min

  Send 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, literally,...