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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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 of who we are, where we’ve been, and what matters most.
@04:32 The History – Where tattoos began and how views have changed
@06:40 First Impressions – Our early tattoos and what people thought
@17:10 Personal Stories – The strawberry, dolphins, and butterflies
@26:00 Travel Ink – Tattoos from Ecuador, Costa Rica, and India
@30:00 Anniversary Ink – Matching tattoos in Japan
@35:06 Love & Family – Vows, kids, and tattoos as journals
@42:02 Tattoo Tips – Safety, regrets, and what we’ve learned
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
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!
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.
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.
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.
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 story about more than walking away from flying planes - it’s about growing up, challenging assumptions, and realizing that changing your mind can be the bravest thing you do.
@02:35 The Dream – Why Largo always wanted to be a pilot @07:48 Reality Check – The moment things shifted @13:12 Reframing – Letting go and looking deeper @19:45 Critical Thinking – A new way of approaching decisions @26:20 Support – Family, friends, and mentors @31:55 What’s Next – Exploring new passions and possibilities @38:40 Weekly Challenge – Question one belief you’ve always held
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
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!
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.
#37 - Building a Library in Cambodia with Largo Sueiro - The WHY Matters Podcast
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 was about bringing joy, learning, and hope to hundreds of children. And it all started with one teenager’s vision.
@07:11 The Vision – Where it started @13:02 Support – Donations and grants @18:28 Fixing Up – Roof, paint, and shelves @22:45 Community – Kids and helpers join in @31:12 Challenges – Heat and deadlines @37:16 Opening Day – Chalk and ribbon-cutting @41:10 Next Steps – More books and teachers @48:57 Weekly Challenge – Do one small thing
To Donate books for the library: Trask P.O. box 242 Old Orchard Beach, Maine 04064
FREE College Application Session This program will be offered FREE for families! When you register, a Zoom link will be emailed to you. • Wednesday 8/20 at 1pm EST/5pm GMT • Wednesday 8/20 at 6pm EST/10pm GMT • Thursday 8/21 at 8am EST/12pm GMT
Fill out the Google Form to register for these free and helpful sessions!
#36 - Hiking the Appalachian Trail with Jessica & Largo - The WHY Matters Podcast
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, into a slower, more connected way of being. This is a story of resilience, reinvention, and what happens when you step outside your comfort zone with the people who know you best. Whether you're dreaming of the thru-hike life, craving a digital detox, or curious what it’s like to spend half a year in the woods with your teenage kid, this episode is packed with honesty, insight, and a few laughs.
@01:54 Life After 68 Countries – How nomadic travel shaped their worldview @06:20 School on the Trail – Balancing AP exams and miles @10:47 Trail Names & Meaning – Meet “Sunshine” and “Captain” @14:30 The Mental Game – What really gets you through 2,000 miles @18:01 Family Dynamics – Lessons from a mom-son thru-hike @22:45 Hiking With WiFi – Making compromises to make it happen @26:12 Breaking the Mold – Why adventure can’t wait for retirement @30:00 Final Thoughts – Would they do it again?
Ready to rethink adventure, effort, and what it means to come home? Press play.
Want more stories like this? Check out Zero to Travel for deep dives into nomadic living and purposeful exploration.
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
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 finding healing through radical self-care, this episode dives into the deeper truths of long-term travel that Instagram won’t show you. If you’ve ever dreamed of a nomadic lifestyle or felt like your problems might disappear if you just hit the road, this episode is your invitation to think deeper, go slower, and heal smarter.
@00:58 A Decade on the Road – Why they’re still traveling after 10 years @02:00 Romanticizing Travel – How it exposes (not fixes) what’s really going on @06:17 Kids, College & Change – What it’s like launching a child while living nomadically @10:16 Mental Health on the Move – Therapy, trauma, and what nearly broke them @17:04 The Hoffman Process – How a weeklong intensive changed their life @25:27 Working While Wandering – The challenges of building a business on the road @33:39 Together 24/7 – What they’ve learned from parenting, partnering, and producing as a team @40:48 Advice for Long-Term Travelers – What they wish they’d done sooner
This episode is a love letter to doing the work, both inner and outer, and choosing a life that aligns, even when it’s messy. Whether you're a seasoned traveler or just curious what’s beyond the highlight reel, hit play. There’s wisdom here worth carrying.
Want more stories like this? Check out Zero to Travel for deep dives into nomadic living and purposeful exploration.
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.PATREON
#34 - Life on the Road with WorldTowning - The WHY Matters Podcast
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 powerful reframes, we explore how choosing an unconventional life can lead to greater alignment, tighter family bonds, and a new definition of freedom. Whether you're a digital nomad, travel dreamer, or just rethinking what stability looks like, this episode invites you to challenge the script and make intentional choices — even when they’re scary.
@01:54 Leaving Suburbia – The “aha” moment that sparked their world travels @06:27 Fitting Into Boxes – Why society’s version of success wasn’t cutting it @10:16 Financial Reality – What selling everything really bought them @16:43 Raising Kids on the Road – The ups, downs, and surprising benefits @23:05 Conflict & Growth – What travel taught them about relationships @29:48 Unexpected Anchors – When freedom needs a little structure @36:21 Home Is a Feeling – Letting go of the white-picket-fence myth @42:33 Advice for the Hesitant – What they wish they’d known before leaping
Ready to redefine what “normal” looks like? Press play.
Want more stories like this? Check out Zero to Travel for deep dives into nomadic living and purposeful exploration.
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
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, sparks unexpected passions, and builds resilience - even when student loans loom large. Whether you're a parent debating tuition, a student questioning the system, or just someone curious about the fight for intellectual freedom, this episode reveals why education is worth defending (and how to make it work for you).
@02:18 Small-Town to Syracuse – How university exploded our worldviews
@08:45 The Plumber vs. The Accountant – Debunking the "college isn't worth it" myth
@14:22 Harvard vs. The Government – Why politicians fear educated minds
@19:37 Dry Spells of the Mind – What happens when we stop learning?
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 opportunity.
Drawing from our 11 years of full-time travel and unconventional education, we challenge the myth that “book smarts” don’t matter in the real world. Whether you’re a college grad, self-taught expert, or just someone who values truth, this episode will make you think twice about what we lose when we stop valuing knowledge.
@02:18 Spirit Airlines Fiasco – When unreliable flights teach life lessons
@08:45 Defining Intellectualism – It’s not what you think (and yes, you count)
@14:22 Education vs. Learning – Why college isn’t just about degrees
@19:37 Our Big Realization – How travel changed our view of education
@25:51 Avalon’s College Breakthrough – What travel couldn’t teach our daughter
@31:06 The YouTube University Myth – Why fact-checking matters
@36:44 Anti-Intellectualism Red Flags – From book bans to flat earthers
@42:15 Your Challenge – Question one assumption this week
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
PATREON
#31 - A Year Without Sex - The WHY Matters Podcast
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 our decade of full-time travel and unconventional living, we dissect the language of desire, the silent impacts of deprivation, and the creative ways we kept our bond alive - even when traditional romance felt impossible. Whether you’re navigating a dry spell, long-distance love, or just the daily chaos of family life, this episode offers a lifeline for staying connected when life gets in the way.
@02:18 Trail Separation – How distance changed our intimacy
@08:45 Tiny Space Reality – Sex life in one shared room with family
@14:22 Normalizing Dry Spells – No such thing as a perfect couple
@19:37 Sex & Science – How deprivation affects relationships
@25:51 Creative Solutions – Bathrooms, bread runs, and more
@31:06 Kids & Desire – Why we're open with our son
@36:44 Small Gestures – How we stayed connected (cheese > roses)
@42:15 Your Challenge – Break one intimacy barrier this week
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
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!
#30 - The Things We Never Say to Our Kids - The WHY Matters Podcast
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, more supportive family dynamic.
From gendered labels like "princess" to well-meaning but harmful comments like "You’re just like your mother," we break down why these words stick—and how to replace them with empowering language. Plus, we tackle financial phrasing ("We can’t afford that"), emotional validation ("I’m disappointed in you"), and the power of letting kids trust their own instincts.
@203:51 The Power of Language – How words shape a child’s inner voice.
@13:52 Gender Stereotypes – Why "princess" and "boys don’t cry" need to go.
@18:16 Appearance Comments – The harm in "You’ve gained weight" and "Smile for the camera."
@23:32 Emotional Intelligence – Alternatives to "I’m disappointed in you."
@32:13 Generational Patterns – Breaking cycles of shame ("Because I said so").
@37:48 Practical Alternatives – Phrases like "You’re enough" and "Trust yourself."
@43:25 Family Challenge – Listen to this episode with your kids and discuss!
Leave us a voice message! Share your thoughts or questions at info@thewhymatterspodcast.com or call 424-442-9295.
PATREON
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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.
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.
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!
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.
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.
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!
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.
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.
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.
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!
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.
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.
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.
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!
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.
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.
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.
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!
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.
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.
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.
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!
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.
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.
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.
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.
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.
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.
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!
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.
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.
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.
