
The WHY Matters
The WHY Matters is a podcast hosted by Jessica and Will from WorldTowning, sharing the highs, lows, and unexpected moments of their decade-long full-time travel lifestyle. They explore the deeper motivations behind their choices and the positive outcomes those choices have brought. The show aims to offer insights from their experiences as full-time travelers, helping listeners apply those lessons to their own lives. It's a mix of personal stories, laughter, and practical takeaways for anyone considering a life of travel.
Episodes

#55 - Women’s Month: Travel, Courage & Alignment - The WHY Matters Podcast
Send us Fan MailIn 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

#54 - Women’s Month: Corporate Life to Full-Time Travel: Alignment Over Comfort - The WHY Matters Podcast
Send a textIn 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

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

#52 - What Trumpers Need - The WHY Matters Podcast
Send a textIn 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

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

#50 - Our 2026 Goals - The WHY Matters Podcast
Send a textIn 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 sea

#49 - When Grief Takes Over - The WHY Matters Podcast
Send a textIn 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,

#48 - 2025 Recap! - The WHY Matters Podcast
Send a textPATREONhttps://www.patreon.com/worldtowningIf 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 TRIPShttps://worldtowningvoyages.com/Come travel with us! Our company is owned (and 100% guided) by a family of four full-time travelers. Our passion is build

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

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

#45 - Taking a Rest - The WHY Matters Podcast
Send a textIn 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 paren

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

#43 - Celebrating Homeschooling Milestones - The WHY Matters Podcast
Send a textIn 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

#42 - The Wake-Up Call - Aging, Adventure, and Why We Can’t Wait - The WHY Matters Podcast
Send a textIn 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, push

#41 - Living in a Hotel - The WHY Matters Podcast
Send a textIn 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 neve

#40 - Living Our Retirement Dreams in Our 40s - The WHY Matters Podcast
Send a textIn 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 oc

#39 - Why All The Tattoos - The WHY Matters Podcast
Send a textIn 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

#38 - The Pilot Who Pivoted - The WHY Matters Podcast
Send a textIn 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

#37 - Building a Library in Cambodia with Largo Sueiro - The WHY Matters Podcast
Send a textIn 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 sh

#36 - Hiking the Appalachian Trail with Jessica & Largo - The WHY Matters Podcast
Send a textIn 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

#35 - 10 Years of Full-Time Travel with WorldTowning – The WHY Matters Podcast
Send a textIn 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.F

#34 - Life on the Road with WorldTowning - The WHY Matters Podcast
Send a textIn 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 storie

#33 - Why University - The WHY Matters Podcast
Send a textIn 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 universi

#32 - Fighting the Anti-Intellectualism Movement - The WHY Matters Podcast
Send a text 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

#31 - A Year Without Sex - The WHY Matters Podcast
Send a textIn 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 m

#30 - The Things We Never Say to Our Kids - The WHY Matters Podcast
Send a textIn 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 altern

#29 - Our Recent Health Kick - The WHY Matters Podcast
Send a textIn this episode we dive into our kealth kick—a commitment to thriving, not just surviving, as they age. Drawing from a decade of full-time travel, we share hard-won insights on exercise, diet (goodbye caffeine, alcohol, and sugar!), meditation, and sleep hygiene. We reveal the apps (MyFitnessPal, Apple Health) and mindset shifts powering our progress, plus the real challenges of sustain

#28 – The Power of Meditation with Our Dear Friend Doug - The WHY Matters Podcast
Send a textIn this episode we interview our close friend Doug, an experienced meditation practitioner and teacher. We delve into the profound benefits of meditation, sharing personal stories and insights on how meditation has helped us handle stress, improve interpersonal relationships, and discover our authentic selves. Doug discusses his journey from curiosity to becoming a certified meditation

#27 - Appalachian Trail vs Camino Francés - The WHY Matters Podcast
Send a textIn this episode of the Why Matters podcast, we) delve into the differences and unique experiences of hiking the Appalachian Trail (AT) compared to the Camino Francés. We cover a wide range of topics, including preparation, gear, cultural experiences, and the physical and emotional challenges of each trail. Jessica shares personal anecdotes and insights from her own hikes, and we discuss

#26 - How We are Surviving in the US - The WHY Matters Podcast
Send a textIn this episode, we discuss the financial challenges of living in the United States after a decade of full-time travel. We share various strategies and hacks they employ to manage expenses, focusing on accommodation, food, transportation, and entertainment. Highlights include using Black Friday deals for long-term hotel stays, leveraging the Too Good To Go app for discounted meals, maxi

#25 - The Pivots We’ve Had to Make - The WHY Matters Podcast
Send a textToday, we’re diving into the messy, scary, and sometimes hilarious world of pivots. Spoiler alert: pivots are not easy, but they’re necessary for growth, fulfillment, and chasing those big dreams.We kick things off with a little update from sunny (well, 16-degree) New Jersey, where we’re currently thawing out from winter and reminiscing about the best pizza we’ve had in ages (shoutout t

#24 - Why We document Our Lives and Why You Should Too - The WHY Matters Podcast
Send a textIn this episode, we discuss our passion for documenting life and the reasons behind it.We’ll take you through our journey of capturing memories through various mediums like vlogs, blogs, photos, and, most recently, a book. Jessica shares her experience of writing her upcoming book, which highlights a transformative journey on the Appalachian Trail with our son. We also explore the impor

#23 - Journey Through the Appalachian Trail (Special Guest - Largo) - The WHY Matters Podcast
Send a textIn this episode of the Why Matters podcast, hosts Jessica and Will welcome their son Largo, also known as Captain Sueiro, to discuss their extensive six-month hike on the Appalachian Trail. They delve into their experiences, from the reasons for undertaking the hike to the unique dynamics of hiking together as mother and son. The episode touches on schooling on the trail, the challenges

#22 - Teaching our Kids to Fight for Democracy (Special Guest - Avalon) - The WHY Matters Podcast
Send a textWe return after a long hiatus, joined by our daughter Avalon Sueiro.We discuss Avalon's journey in reviving the dormant CMU College Democrats club at Carnegie Mellon University. Avalon, a junior student at the Tepper School of Business, shares her experiences in political activism, organizing events, and overcoming challenges, including leading an effort to paint the campus fence f

Mini Episode 3 - Why Our Marriage Works - The WHY Matters Podcast
Send a textWant to know our secret to a 24-year marriage?In this episode, we share how important it is to have shared adventures while also supporting personal projects. In our relationship, we reject traditional gender roles, allowing ourselves to do anything to help each other. Maintaining a youthful mindset, effective communication, and a deep understanding of each other have been life-changing

Mini Episode 2 - What We Do For Memories - The WHY Matters Podcast
Send a textWhat would you do for a memory?Despite battling tendonitis, I reflect on my memories and the sacrifices I'm willing to make for them. I open up about my struggles with perfectionism, the physical pain of my injury, and my deep desire to prioritize experiences over material possessions. As I prepare to rejoin the hike, I hope to inspire you to consider your own "whys" and

Mini Episode 1 - Would We Let Largo Hike Alone? - The WHY Matters Podcast
Send a textAre we letting Largo hike the AT Trail alone?Largo recently asked if we would allow him to finish the trail alone if Jessica couldn't continue. Life is full of uncertainties, and if Jessica is unable to finish, we would permit Largo to continue under specific guidelines. As he grows older, he needs less of our assistance and more opportunities to navigate life independently. Allowi

#21 - Perfectionism - Embracing Progress Over Perfection - The WHY Matters Podcast
Send a textOne of the best ways to overcome perfectionism is to celebrate your successes, no matter how small they may seem. Each step forward is progress.We haven't been posting for a while, and it's been hard for us because of Jessica's perfectionism. People's judgments hit us hard and really take a toll, pushing us to strive for perfection. We need to embrace the small steps

#20 - The Reality of Sexual Abuse, Therapy and Healing - The WHY Matters Podcast
Send a textTrigger Warning: We will discuss about sexual abuse. This may be triggering for you. We respect your decision to skip this episode. Listen again when we are back to our regular programming. “The healing begins, but it doesn't happen immediately.”One in six men experiences sexual abuse or assault. People do not see the aftermath of the trauma; many hide it, and it causes them to cru

#19 - How the Hoffman Process Changed our Life - The WHY Matters Podcast
Send a textTrigger Warning : This episode discusses mental health issues that you may find triggering. Feel free to skip this episode. “You have to be willing to look within yourself and be willing to change certain things that have been part of your life.”We were referred to undergo Hoffman Process, and we were surprised to learn of its existence. What is it? It's joining a group with 24 ind

#18 - How Different Kinds of Therapy Can Be Good for Your Mental Health - The WHY Matters Podcast
Send a textYour Mental Health Matters!We all go through struggles; life will always come with its own problems. Finding ways to overcome them is the way to go. Will and I have gone to great lengths in trying a variety of therapies. Our Mental Health Journey is a win not just for our relationship, but also for our family. Keep trying until you find the perfect therapy that works for you!Welcome to

#17 - Appalachian Trail 6-Month Thru-Hike: My First Impressions - The WHY Matters Podcast
Send a textWhy did Largo and I hike the Appalachian Trail?Well, it's like opening a whole new world! This trail is tough, really tough. But you know what's amazing? Even though not many make it through, folks still want to give it a shot. Everyone has their own reasons for taking on this adventure. And you know what it teaches us? It's not just about walking a path. It's about

#16 - Our Life Updates, AT Trail, Bear Horn Mishap, Boat Life, Quitting Full-Time Travel and More - The WHY Matters Podcast
Send a textWe answered your questions and shared our life update!The AT Trail has changed our current lifestyle. Will and I are currently apart; he is busy editing the delayed vlogs while Largo and I are having the best days of our lives here. However, we want to update you on how things are working for us and share our future plans because some of you may be wondering if our full-time travel life

#15 - Why We Let Our Kids Swear - The WHY Matters Podcast
Send a textWould you let your kids swear?Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of pur

#14 - Building a Lasting Legacy - Living For More Than Our Ego - The WHY Matters Podcast
Send a textWhat’s your Legacy?Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of purpose.Discov

#13 - Sharenting: Protecting Your Child’s Privacy on Social Media - The WHY Matters Podcast
Send a textIt’s their choice!Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of purpose.Ever wo

#12 - Pursuing Passion: Real Talk on WHY WorldTowning if it Does Not Pay the Bills - The WHY Matters Podcast
Send a textIs it worth it to work for FREE on something you believe in?In this episode, we discover the “Why” of our purpose. Exploring life with WorldTowning through the years were the best times of our life. We lived in a purpose-driven life, where we set our goals and actually achieve them. Through full time travel we have reached high levels of empathy, looking into the diversity of lives of p

#11 - Reverse Culture Shock: Returning to the USA After 10 Years Away
Send a textWhat is Reverse Culture Shock? Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of pu

#10 Are Full-Time Travelers Homeless? - The WHY Matters Podcast
Send a textWhere is Home?Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of purpose.Considering

#9 - TEN MISTAKES We Made and The Lessons Learned - The WHY Matters Podcast
Send a textYou just gotta learn the hard way, don’t you?In this episode, we go back in the archives to uncover ten (OK - Maybe eleven) interesting, and oftentimes hilarious, mistakes that we have made over the last couple of years. We dive deep into the idea that mistakes are not only okay but essential for growth. We emphasize the importance of owning up to errors, reframing them positively, and

#8 - Parenting, Romancing, Traveling and Running a Business with your Partner 24/7 - The WHY Matters Podcast
Send a textWondering how to survive with your partner as you spend 24/7 together while Parenting, Romancing, Traveling, and Running a Business? In this episode, we share honest perspectives and useful guidance for maintaining love in the midst of adversity, as well as strategies for nurturing love in the face of challenges in life. We provide helpful advice for sustaining a healthy relationship,

#7 The power of saying NO. How one choice changed our entire life. - The WHY Matters Podcast
Send a textSaying ‘No’ is fineWelcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of purpose.In thi

# 6 - Why is it so Hard to ask for Help? Embracing Support Without Shame! - The WHY Matters Podcast
Send a textIt’s Fine to ask for help!Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of purpose

#5 - Why you should do those physical adventures before it’s too late. Our most dramatic decision yet. - The WHY Matters Podcast
Send a textJust go for it!Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of purpose.In this ep

# 4 - The Importance of Sleeping with Strangers and Picking Up Hitchhikers - The WHY Matters Podcast
Send a textBe Confident with Strangers!Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of purpo

# 3 - How to Implement Boundaries and Their Importance to Discovering Your ‘Why’ - The WHY Matters Podcast
Send a textBoundaries pave the path to greatness and serenityWelcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a

# 2 - Deciding to Move Off Our Boat: How We Lost Sight of Our WHY - The WHY Matters Podcast
Send a textYour 'Why' is what truly matters.Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong

# 1 - Beating Fear at Its Own Game: How We Transitioned Our Life into Full-Time Travel - The WHY Matters Podcast
Send a textReady for Adventure?Welcome to 'The Why Matters Podcast,' where we explore life lessons, things we often take for granted, and everything in between, gathered from our decade-long full-time travel lifestyle. Each week, we'll delve deep into the 'why' behind the choices we humans make in life and the positive results that stem from a strong sense of purpose.In th

Podcast Premieres Wednesday, January 17th - The WHY Matters Podcast
Send a textHi friends! Today is very exciting for Will and I as we are finally launching our podcast “The WHY Matters,” which we have been discussing and dreaming about for years. We have poured our heart and soul into this new endeavor, and we hope you love it as much as we have enjoyed producing it.We left the US with our children ten years ago for a one-year adventure, and we are still at it, b
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