The WHY Matters

WorldTowning

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.

  1. MAR 4

    #53 - Saying BYE to Trumper Friends | Who Gets a Seat at Your Table?

    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 superior, but about having clarity, boundaries, and integrity. From lifelong friendships and neighborhood communities, to church groups, nostalgia, fear of loneliness, and the temptation to “agree to disagree,” this conversation challenges listeners to examine why they stay connected and who that silence ultimately protects. This episode isn’t about politics for the sake of politics. It’s about empathy, responsibility, and the courage it takes to walk away when something no longer aligns with your values. We share personal experiences cutting ties, rebuilding community, navigating friendship as full-time travelers, and why community matters, but not at the expense of your conscience. It’s raw, opinionated, reflective, and deeply human, and an invitation to ask a harder, more honest question: What does it cost us to stay comfortable instead of standing for what’s right? @04:27 Choosing Values Over Comfort – why this conversation matters @06:39 Friendship vs. Morality – when politics becomes about humanity @10:20 Asking the Hard Question – voting, silence, and accountability @16:11 Childhood Friends – when history doesn’t override harm @26:13 Neighbors & Proximity – community without moral exemptions @31:55 Faith & Integrity – why belief labels aren’t enough @40:25 Rebuilding Community – letting go to make space for aligned connections Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295. 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 minds alongside a community of like-hearted individuals. COACHING https://worldtowning.com/learn-2/ Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else. NEWSLETTER https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa 10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life. MERCHANDISE Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/ Support the show

    57 min
  2. FEB 25

    #52 - What Trumpers Need - The WHY Matters Podcast

    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 tools, language, and self-awareness. From generational patterns and social conditioning, to masculinity, femininity, anger, fear, and nostalgia for a past that never really existed, this conversation challenges listeners to look inward instead of projecting pain outward. This episode isn’t about politics for the sake of politics, it’s about empathy, responsibility, and the courage it takes to face yourself. We share personal experiences with therapy, why it’s a practice and not a one-time fix, and how doing the daily “gym for the brain” creates more space for compassion, clarity, and peace. It’s raw, opinionated, reflective, and deeply human, and an invitation to ask a harder, more honest question: What happens when we choose to do the work on ourselves? @05:34 Unprocessed Trauma – How pain recruits beliefs and enemies @10:42 Social Conditioning – “Be a man,” beauty standards, and buried emotions @15:27 Accountability – Trauma as context, not an excuse @19:50 Why We Went to Therapy – When self-awareness isn’t enough @26:01 Therapy Is a Practice – Tools, not a cure @30:00 Authentic Living – Who you are when no one is listening Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295. 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 minds alongside a community of like-hearted individuals. COACHING https://worldtowning.com/learn-2/ Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else. NEWSLETTER https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa 10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life. MERCHANDISE Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/ OUR SOCIALS Instagram: https://www.instagram.com/worldtowning/ YouTube: Support the show

    55 min
  3. FEB 18

    #51 - Why Learning a New Language Matters - The WHY Matters Podcast

    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 between understanding and actually speaking, and how AI and translation tools are changing the game. Camille reminds us that learning a language is brain gymnastics, it takes patience, humor, and actually doing the work. @05:12 Native vs. Non-Native Teachers – Why accent matters @10:06 Doing the Work – Grammar, patience, and progress @14:10 TV & YouTube – Helpful or limiting? @21:02 AI & Translation – Tool or crutch? @23:49 Make It Fun – Humor and brain flexibility We also share Camille’s French music recommendation, La symphonie des éclairs by Zaz, as a beautiful way to immerse yourself in the language. If you’d like to work with Camille, you can find her at artfulfrench.com or email her directly at artfulfrench@gmail.com. This episode isn’t just about French. It’s about humility, growth, and having the courage to sound foolish while you learn something new. Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295. 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 minds alongside a community of like-hearted individuals. COACHING https://worldtowning.com/learn-2/ Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else. NEWSLETTER https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa 10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life. MERCHANDISE Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/ OUR SOCIALS Instagram: https://www.instagram.com/worldtowning/ YouTube: https://www.youtube.com/worldtowning Facebook: https://www.facebook.com/worldtowning Tik-Tok:  https://www.tiktok.com/@wo Support the show

    1h 5m
  4. FEB 11

    #50 - Our 2026 Goals - The WHY Matters Podcast

    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 adulthood, and no clear three-year plan for the first time in decades, Jessica and Will explore how flexibility, self-compassion, and evolving priorities are shaping the year ahead. From writing books and learning French for a long-stay visa in France, to running 1,000 miles, lowering cholesterol naturally, strengthening their marriage on the Camino Norte, and redefining what travel looks like as near-empty nesters, this episode is about ambition without pressure and growth without perfection. It’s not about crushing every goal.  It’s about choosing what matters in this season, allowing space for life to unfold, and aiming for progress over perfection. @01:09 — Welcoming 2026 and Letting Go of 2025  @08:56 — Personal Goals: Books, French, Launching the Kids  @21:04 — Business Vision: Writing, Coaching, and Podcast Plans  @26:22 — Health Reset: Meditation, Movement, and Longevity  @29:27 — A 25th Anniversary Camino and Travel in a New Season  @37:49 — What Success Actually Looks Like in 2026 Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295. 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 minds alongside a community of like-hearted individuals. COACHING https://worldtowning.com/learn-2/ Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else. NEWSLETTER https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa 10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life. MERCHANDISE Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/ OUR SOCIALS Instagram: https://www.instagram.com/worldtowning/ YouTube: https://www.youtube.com/worldtowning Facebook: https://www.facebook.com/worldto Support the show

    40 min
  5. FEB 4

    #49 - When Grief Takes Over - The WHY Matters Podcast

    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 about honoring it and learning how to live alongside it, one day at a time. @02:05 — Why We’re Talking About Grief @07:45 — Losing a Best Friend @12:40 — When Grief Takes Over @19:30 — The Messy Parts of Grief @31:55 — Hiding Pain From the World @42:35 — Carrying Them With You @1:06:56 — Living With Grief Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295. 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 minds alongside a community of like-hearted individuals. COACHING https://worldtowning.com/learn-2/ Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else. NEWSLETTER https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa 10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life. MERCHANDISE Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/ OUR SOCIALS Instagram: https://www.instagram.com/worldtowning/ YouTube: https://www.youtube.com/worldtowning Facebook: https://www.facebook.com/worldtowning Tik-Tok:  https://www.tiktok.com/@worldtowning @02:05 — Why We’re Talking About Grief @07:45 — Losing a Best Friend @12:40 — When Grief Takes Over @19:30 — The Messy Parts of Grief @31:55 — Hiding Pain From the World @42:35 — Carrying Them With You @1:06:56 — Living With Grief Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295. PATREON https://www.patreon.com/worldtowning If you would like to support us in a greater capacity where you can Support the show

    1h 7m
  6. JAN 14

    #47 - A Mother–Daughter Journey on the Appalachian Trail - The WHY Matters Podcast

    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 navigating injury from day one. As miles passed and pain accumulated, their hike became a living lesson in boundaries, communication, and the quiet tension between ambition and limitation. Through stories of injuries, missed miles, separation on trail, and moments of deep connection, they unpack how perseverance can slowly turn into self-betrayal—and how listening to your body can feel like failure in a culture that glorifies suffering. Together, they reflect on burnout, guilt, and the courage it takes to rest, especially when someone you love is still moving forward. This conversation reframes resilience not as stubbornness, but as wisdom—and reminds us that recovery is not weakness, but strength. You can hear more from them on: https://youtube.com/@kelseyontheat?si=gEgr3BfGPDQcd88y @04:05 – Who Jamless and Green Bean are, and why they hiked together @07:58 – Starting injured: ignoring the early warning signs @11:44 – Different bodies, different limits, same trail @15:32 – When “hike your own hike” isn’t that simple @18:59 – The emotional toll of slowing someone you love down @22:41 – Burnout, anxiety, and why the trail forced honesty @26:18 – Guilt, pain, and the moment perseverance broke @29:06 – Separating on trail: choosing health over pride @31:48 – Redefining resilience through recovery and compassion Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295. 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 minds alongside a community of like-hearted individuals. COACHING https://worldtowning.com/learn-2/ Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else. NEWSLETTER https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa 10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life. MERCHANDISE Yes - We have Merch! - https://worldtowningvoyages. Support the show

    1h 41m
  7. JAN 7

    #46 – The Power of Meditation with Our Dear Friend Doug - A Tribute

    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 is not about perfection, but presence. We are re-releasing this episode in honor of Doug. Not as a goodbye, but as a thank you. In this conversation, we talk with Doug, an experienced meditation practitioner and teacher, about the impact meditation has had on his life. He shares his journey into meditation, lessons from silent retreats, and practical guidance for anyone curious about starting a practice. If this is your first time hearing Doug, we hope you feel what we felt knowing him. If you have listened before, we hope you hear it differently this time. This one is for you, Doug. We love you. Namaste. Leave us a voice message and send it over to us at info@thewhymatterspodcast.com You can call us and leave us a voicemail at 424 442 9295. Doug’s Udemy Course: https://www.udemy.com/course/mantra-meditation/?referralCode=C292FCAF98C545866D17 01:15 Introducing Our Special Guest: Doug 08:14 Doug's Journey into Meditation 11:52 Understanding Meditation and Its Benefits 16:30 Doug's Meditation Training and Teaching 22:18 The Challenges and Realities of Meditation 26:38 The Power of Meditation During COVID 28:14 Experiencing a Silent Retreat 37:07 Daily Meditation Practices 41:48 Starting Your Meditation Journey 47:43 Final Thoughts and Reflections 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 minds alongside a community of like-hearted individuals. COACHING https://worldtowning.com/learn-2/ Are you looking for guidance to accomplish that big goal supporting your why? We are the couple for you. Let’s set up a chat to get you started on your dream life, whether it is full-time travel or something else. NEWSLETTER https://worldtowning.us14.list-manage.com/subscribe?u=32de323857a58dc5ab35b897f&id=b0760c6efa 10 years full-time travel with 2 world schooled kids, currently on a sailboat, writing about a travel lifestyle, education, equality & what it’s like to live an unconventional life. MERCHANDISE Yes - We have Merch! - https://worldtowningvoyages.com/elements/merch/ Support the show

    54 min
5
out of 5
52 Ratings

About

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.

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