The WHY Matters
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.
Episodes
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...
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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 cu...
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 ph...
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 light...
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 ex...
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 Bo...
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 ...
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...
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:
...
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...
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 u...
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 hi...
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 light...
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 me...
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 ...
In this episode of The WHY Matters Podcast, we unpack the beautifully chaotic life of full-time travelers and what it really means to "sell it all and go." From ditching suburban routines to chasing connection across continents, WorldTowning founders Jessica and Will dive deep into the emotional, financial, and relational side of radically redefining home.
Through honest stories, hard-won lessons, and powerfu...
In this episode of The WHY Matters Podcast, we tackle the hidden value of university education - beyond the paycheck. From hiking the Appalachian Trail of intellectual growth to cramming into the tiny dorm room of modern skepticism, we explore why higher education is about more than just degrees and job prospects.
Through personal stories and eye-opening stats, we break down how university reshapes worldviews, spa...
In this episode of The WHY Matters Podcast, we tackle the growing distrust of education and expertise in today’s world. Through personal stories and hard facts, we break down what anti-intellectualism really means - and why it matters more than ever. From our son’s chaotic Spirit Airlines nightmare to our daughter’s life-changing college experience, we explore how real learning happens when curiosity meets opportunit...
In this episode of The WHY Matters Podcast, we unpack the unplanned year-long dry spell that reshaped our relationship - from hiking the Appalachian Trail in separate states to sharing a one-room hotel with our teenage son. Through candid stories and hard-won insights, we explore how intimacy evolves (or collapses) under extreme circumstances, and why physical connection is about far more than sex.
Drawing from o...
In this episode of The WHY Matters podcast, we dive into the language we use with our children by exploring how common phrases, often passed down through generations, can unintentionally shape their self-esteem, emotional intelligence, and sense of identity. Drawing from a decade of parenting and full-time travel, we share personal stories, research-backed insights, and practical alternatives to foster a healthier, mo...
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