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. 1 DAY AGO

    #49 - 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
  2. 4 FEB

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

    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 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 c Support the show

    1h 7m
  3. 14 JAN

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

    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, 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://worldtowningvoyag Support the show

    1h 41m
  4. 7 JAN

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

    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 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. 12/11/2025

    #44 - Taking a Rest - The WHY Matters Podcast

    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-betrayal - and how true endurance requires recovery. They also challenge the myth that rest is weakness, arguing instead that the power to rest is the power to endure. @04:12 – When perseverance turns into burnout  @09:26 – The trail story that changed Jessica’s view of rest forever  @13:05 – Why they stepped off the boat (and what it cost them)  @16:05 – The guilt of slowing down and losing followers  @18:46 – Passion vs. punishment: knowing when to pause  @20:23 – The shame cycle of productivity  @22:26 – How our “suck it up” culture gets passed on to our kids  @27:25 – Redefining resilience: why recovery is strength @29:16 – Missing deadlines, guilt, and the courage to rest anyway 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 Support the show

    40 min
  6. 22/10/2025

    #44 - Raising Trilingual Kids: The Real Cost, Chaos, and Magic of Multilingual Living

    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 raising multilingual kids — what worked, what didn’t, and what it really costs (financially and emotionally). @04:18 – Why we believe language is the bridge between worlds @08:14 – The surprising lifelong benefits of learning a second (or third) language @18:24 – How we accidentally discovered France’s free immersion education system @27:42 – What we paid at each stage — from $580/month preschool to free public school abroad @43:11 – The honest truth about bad teachers, language tears, and firing tutors @59:20 – Myth-busting: why kids don’t just “pick up” a language on the playground @1:10:45 – Our biggest takeaways and why giving your child another language is the best gift you’ll ever give 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 Support the show

    1h 10m
  7. 08/10/2025

    #43 - Celebrating Homeschooling Milestones - The WHY Matters Podcast

    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 how families can create meaningful, personal traditions that honor effort, growth, and adventure. @04:28 – Why this topic hit home and what inspired the episode @06:50 – Why families often overlook homeschool achievements @09:59 – Surprising stats showing homeschoolers thrive academically and socially @13:30 – How we celebrated Avalon’s graduation at sea @20:08  – Finding meaning (and joy) even when others don’t show up 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 Support the show

    25 min

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.