• 40 minutes 55 seconds
    Y We Travel Podcast: To Meet The Neighbours (Bonus Episode!)

    This week, I'm sharing a bonus episode from a brand new podcast called Y We Travel, co-hosted by my friend Eric Weiner, who has joined me on the show a few times over the years. Eric is a New York Times bestselling author and former foreign correspondent, and his co-host Erica Vella is an award-winning podcaster and former broadcast journalist. 

    There's no shortage of travel advice out there — who can save us a buck, what to do, when's the best time to go, where to go. But one fundamental question often gets left behind: why? 

    Born from an award-winning magazine series of the same name, Y We Travel explores the deeper motivations behind our journeys. The show unpacks the emotions, discoveries, and purpose that give travel its meaning. 

    In this episode, Eric and Erica discuss the origins of the series and their own motivations for travelling. Eric interviews author and Y We Travel essayist Pico Iyer, trading travel anecdotes from Japan to California to North Korea and discussing themes from Pico's piece in The Walrus magazine, which argued that we should travel to meet our neighbours. Erica continues the conversation with a selection of Toronto Pearson passengers, asking: "Why are you travelling today?" 

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    25 June 2026, 10:00 am
  • 1 hour 18 minutes
    7 Travel Tech Trends Worth Knowing in 2026 + 3 Emerging Hot Spots to Spend Quality Time with Matt Gray

    Matt Gray is the founder and CEO of Pangea, a free social travel app built to help people coordinate travel plans, share recommendations, and connect with their network around the world. After a decade in product development and corporate M&A at a global fintech company, he left the corporate world in 2023 to become a full-time digital nomad and build Pangea full-time. He is on a personal mission to visit every country in the world.

    In this episode, we get into seven travel tech trends shaping how people plan, book, and experience travel, including why most travel apps fail, the rise of social travel, and what AI can and can't do for travelers right now. We also dig into destination recommendations, advice for running a remote business on the road, and what it means to bridge the nomad bubble.

    These are genuinely fascinating times to be a traveler and a builder in the travel space, and Matt sits at the center of both worlds. He's thinking seriously about why travel tech has such a high failure rate, and what it would actually take to crack the code, and he brings a perspective that is grounded in years of on-the-ground experience across dozens of countries and travel styles. There is a real conversation here about the gap between wanting to travel and actually doing it, and I think it will stick with you. The travel tech trends for digital nomads piece is insightful, but the human thread running through it all is what makes this one worth your time.

    Have you ever had a piece of technology genuinely change how you travel or connect with people on the road? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.

    Tune In To Learn:

    • Why so many travel apps are built to solve a single problem, and why that almost always leads to failure
    • How being a "multifaceted traveler" is reshaping what a useful travel platform actually needs to do
    • Why AI wrappers on ChatGPT are not the same as AI-powered travel tools, and how to tell the difference
    • How social travel is changing the reason people book trips in the first place
    • Why off-the-beaten-path destinations benefit most from the rise of connected travel communities
    • How to break out of the nomad bubble and go deeper in the places you visit
    • Why the people you travel with may matter more than the places you go
    • Destination recommendations for regions quietly gaining traction in the nomad world
    • Advice for running a remote team while living a location-independent life
    • What it looks like to bring urgency to travel, not just talk about it
    • And so much more

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    23 June 2026, 10:00 am
  • 1 hour 27 minutes
    How to Live an Unconventional Life of Adventure and Purpose by Becoming “Dirtbag Rich” with Blake Boles

    What would it mean to stop measuring your life by the conventional yardstick and start building one that actually fits? 

    Blake Boles is a writer, experiential educator, and the founder of Unschool Adventures, a travel company for self-directed teenagers, which he has run since 2008. He is the author of several books on alternative education and self-directed learning, and his newest book, Dirtbag Rich: High Freedom, Low Income, Deep Purpose, was released in March 2026.  

    In this episode, Blake and I get into the philosophy behind "dirtbag rich" living, including what it really means to pursue a high-freedom, low-income lifestyle while still navigating the demands of modern capitalism. We also dig into the practical side of how to make a non-traditional financial model actually work, and talk about purpose, downward mobility, unschooling, outdoor adventure, and so much more. 

    If you've ever wondered whether there's a middle path between grinding toward a distant retirement and going full dirtbag with no financial safety net, this conversation is going to give you a lot to think about. Blake shares a lot of real practical substance in this one, alongside some genuinely fresh thinking about how to measure wealth, what freedom actually requires, and what gets in the way of most people finding their version of a dirtbag-rich unconventional life. 

    What does "enough" look like for you, whether that's money, time, adventure, or something else? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message. 

    Tune In To Learn: 

    • Why the original dirtbag culture offers a useful framework, even if you'll never live in Yosemite full-time 

    • How Blake figured out a way to earn good money in short bursts and stay free the rest of the year 

    • Why "how do you know when you're wealthy?" is a more useful question than you might expect 

    • What the FIRE movement often gets wrong about making a clean break from work 

    • How to think about "downward mobility" as a feature rather than a failure 

    • Why having freedom from something isn't enough without also knowing what you're free to do 

    • What the real risks of a dirtbag rich lifestyle actually are, and how to go in with clear eyes 

    • How purpose shows up differently for different people, and why measuring it in "I get to" days works 

    • Advice for attracting the ideal clients and building work that doesn't eat your life 

    • Why getting your ideal client to feel genuinely excited to work with you is the job before the job 

    • And so much more 

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    16 June 2026, 10:00 am
  • 1 hour 6 minutes
    Uruguay: Top 7 Hidden Gems (That Most People Miss) + Testing the Remote Work Lifestyle with Lucia Krygier

    Ever considered traveling to or working from Uruguay? 

    Lucia Krygier is a Uruguayan entrepreneur and innovation consultant based in Montevideo. In early 2025, she spent two months working remotely from Cape Town, South Africa, an experience she describes as a turning point in her life. That trip led her to found Work From Uruguay, a community-driven workation program bringing together remote workers, digital nomads, and entrepreneurs to co-live and co-work in Uruguay. 

    In this episode, Lucia shares her journey from first-time remote worker to budding business owner, and makes a strong case for why Uruguay deserves a spot on your radar. 

    There is something worth sitting with in this conversation about what happens when you stop waiting for the right moment and just go. Lucia's path touches on trusting yourself through uncertainty, building a life around how you actually want to live, and what travel to Uruguay's hidden gems can unlock when you give a place more than a few days.  

    If you had the chance to spend a few months working and traveling somewhere completely new,  would you take it? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message. 

    Tune In To Learn: 

    • Why Lucia's first remote work trip to Cape Town changed the direction of her life 

    • How she decided between constantly moving and staying in one place for an extended time 

    • The hidden costs and benefits of spending more time in one place instead of country hopping 

    • The mindset shift that helped her leave a stable job and launch a business from abroad 

    • How she handled the uncertainty of starting a consulting career while traveling across Europe 

    • Why she built her business around her home country instead of continuing to travel indefinitely 

    • What Uruguay's digital nomad permit is and how it works for long-term visitors 

    • The off-grid beach village that gets a "wow effect" from every single visitor who goes there 

    • Seven specific places in Uruguay worth visiting, from a colonial port town to a bohemian surf village 

    • What to eat in Uruguay, from the national sandwich to a dish tracing back to Italian immigrants 

    • Advice for testing the work-travel lifestyle before committing to a full nomadic year 

    • And so much more 

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    9 June 2026, 10:00 am
  • 1 hour 16 minutes
    How to Transition to a “Normal Life” After Travel with Tom Turcich (10th Person to Walk Around the World)

    What do you do when the adventure ends? 

    Tom Turcich is a motivational speaker, author, and the tenth person in history to walk around the world. Over seven years, he and his dog, Savannah, covered 28,000 miles across 38 countries and six continents, completing the journey in 2022. He is the author of the memoir The World Walk and the children's book Savannah's World of Adventure. 

    In this episode, Tom shares what returning home after long-term travel actually looks like, from the mental and emotional toll of losing the road, to the financial catch-up game, to the harder question of who you are once the adventure is over. 

    If you've ever come back from a trip and felt a strange kind of grief you couldn't quite name, this one is for you. Tom is remarkably open about the difficulty of that first year back, and the conversation gets into territory that doesn't often get talked about after a big journey ends. There's real honesty here about what it takes to find your footing again, how to rebuild adventure into a life that isn't handing it to you every day, and how to make peace with the constraints that come with settling down. 

    What's one thing you've held onto from a big trip that's hard to explain to people who weren't there? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message. 

    Tune In To Learn: 

    • Why Tom describes his first year back as the only depression he's ever experienced 

    • How the world "stops coming at you" when you settle down, and what it takes to rebuild that muscle 

    • The unexpected mental and emotional challenge of no longer having a North Star 

    • Why consistency beats passion when it comes to making progress, in travel and in life 

    • What two years of walking in the Atacama Desert taught Tom about happiness 

    • Why your traveler identity matters less than the values underneath it 

    • How walking became a years-long meditation practice Tom didn't see coming 

    • The one mindset Tom would give anyone coming off the road for the first time 

    • Why building community after a big adventure takes longer than most people expect 

    • What it means to choose your constraints rather than just accept them 

    • And so much more 

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    2 June 2026, 10:00 am
  • 50 minutes 33 seconds
    Give Yourself Permission to Choose Differently: Jason Moore on the My Most Authentic Life Podcast

    What does it actually take to give yourself permission to live unconventionally, and what's really standing in the way? 

    I had the opportunity to be a guest on the My Most Authentic Life podcast with Fede Vargas, a conversation we recorded live on the rooftop at Podcast Movement Evolutions during South by Southwest in Austin, Texas. Fede interviewed me about the themes that run through this show, including unconventional paths, pivots, lifestyle design, and what it means to choose differently. 

    This conversation pulls out some of my most honest thinking on what it means to give yourself permission to live unconventionally. We talk openly about my decade as a nomad with no fixed home, the internal and external forces that push back against unconventional choices, and how imposter syndrome never goes away but can be trained around. There's a lot here that I think will resonate if you've ever felt the pull of a different path but weren't sure you were allowed to take it. 

    Tune In To Learn: 

    • Why giving yourself permission is often the first and hardest obstacle on any unconventional path 

    • How imposter syndrome works as a muscle you can train, not a problem you solve 

    • What it means to "pivot" before you've actually made any outward moves 

    • Why the journey before the journey has more value than most people realize 

    • How lifestyle design is less about optimization and more about filtering decisions through your ideal daily life 

    • Why the "perfect average day" exercise is a practical starting point for anyone designing their life 

    • How I spent a decade as a nomadic tour manager, including driving the Meow Mix Catmobile across the U.S. 

    • What unexpected things can happen when you follow your gut, even last-minute 

    • Why my definition of authenticity comes down to one word 

    • And so much more 

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    26 May 2026, 10:00 am
  • 1 hour 17 minutes
    Turn Travel Into A Lifestyle With Goats On The Road

    What would it take for you to actually turn travel into a lifestyle, not just a vacation? 

    Nick Wharton and Dariece Swift are the Canadian couple behind Goats On The Road, one of the longest-running travel and lifestyle blogs online. Since leaving Canada in 2008, they have lived and traveled full-time across Southeast Asia, Africa, the Middle East, Europe, and the Caribbean, funding their adventures through teaching English abroad, house sitting, freelance writing, and eventually building a successful travel blog and suite of online courses. 

    In this episode, Nick and Dariece share the real, unfiltered story of how two regular people from a small town in Canada traded their office jobs and oil rig shifts for a decade of long-term travel, and how they've figured out how to keep it going. 

    This episode covers what it really takes to make travel a long-term lifestyle, from the mindset shifts that keep you going to the practical ways people actually fund life on the road. Nick and Dariece have been doing this for over a decade and speak honestly about the challenges of traveling as a couple, building an online business from scratch, and knowing when to step back from work and just travel. I also share my own perspective on staying connected to your highest values as your life and travel style evolve. 

    What has been your biggest mental or practical barrier to making travel a more permanent part of your life, and has anything ever helped you push past it? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message. 

    *This is a previously released episode from the archives! Zero To Travel interviews are timeless, offering valuable insight whenever you listen.  

    Tune In To Learn: 

    • What happened after their first 13-month backpacking trip through Southeast Asia that set everything in motion 

    • The beach meltdown in Thailand that led to one of the boldest and most pivotal moves of their travels 

    • What it really takes to travel as a couple 24/7, and the specific things Nick and Dariece do to keep it working 

    • How Goats On The Road started and the shift in approach that became their biggest turning point 

    • Why they almost let video ruin the travel experience, and what they did about it 

    • How they've managed to avoid full burnout after more than a decade of living and working on the road 

    • The mix of jobs and strategies they've used at different stages to keep the travels funded and going 

    • How their travel style has evolved over a decade and what the lifestyle actually looks like for them now 

    • My three principles for keeping travel a lifelong priority, no matter where you are in life 

    • And so much more 

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    21 May 2026, 10:00 am
  • 1 hour 27 minutes
    Top 7 Hidden Gems in Oslo, Norway with Curtis Rojak of Viking Biking

    Oslo doesn't hit you the way other European capitals do. There's no single monument everyone leaves talking about, and yet people consistently walk away from this city with a feeling they can't quite explain. 

    Curtis Rojak is an American expat who has lived in Europe for over 25 years and holds dual Norwegian-American citizenship. He is the founder of Viking Biking, Oslo's premier guided bike and hiking tour company, and has led more than 3,000 tours through Oslo on foot and by bike.  

    This episode is a local's guide to Oslo, recorded in my living room with Curtis. We cover seven hidden gems in the city, from a haunting mausoleum most tourists never find to a private island cabin you can rent for a night on the Oslo Fjord. 

    This episode covers what makes a place feel like home versus just a place you've visited, what it takes to genuinely know a city at a local level, and how to discover the experiences that don't make it into guidebooks. You'll also hear honest conversation about building a life abroad long-term, what draws people to certain places, and why the best travel experiences often come from knowing someone who actually lives there. Curtis brings real depth on Oslo specifically, but the broader themes about place, belonging, and authentic discovery apply to anywhere you're considering visiting or moving to.  

    Have you ever discovered a hidden gem in a city that completely changed how you thought about that place? I'd love to hear your story, and I hope you'll share by sending me an audio message. 

    Tune In To Learn: 

    • Why one of Norway's most extraordinary pieces of art is hidden in a mausoleum most tourists never find, and how to actually visit it 

    • How to spend a Norwegian summer day at a lakeside farm where animals roam free through landscape gardens 

    • Where to find secret sea cliffs near the city, and where locals actually jump from 

    • Why a restaurant on its own private island captures the Norwegian good life better than almost anywhere else in the city 

    • What makes one of Europe's best cocktail bars worth the New York-level prices you'll pay 

    • How to rent a private island cabin on the Oslo Fjord through a local organization almost no tourists know about 

    • Why Curtis believes Oslo's greatest strength is also what most tourists only notice on their last day 

    • What 25 years as an expat taught Curtis about choosing where to live and why gut feeling matters more than logic 

    • How the "Lego Country" exercise surfaces the best things about multiple continents and destinations 

    • And so much more 

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    19 May 2026, 10:00 am
  • 46 minutes 12 seconds
    Remote Roundup: Egypt Solo Travel, Building Intentional Seasons, Managing Daily Travel Stress, Creative Remote Work Workarounds (May 2026)

    From destinations that challenge your assumptions to the routines and mindsets that make this lifestyle actually sustainable, join Caitlin and Janessa as they unpack what's been on their minds this month. 

    Remote Roundup is a monthly series hosted by Zero To Travel's associate producer, Caitlin Sunderland, and partnerships manager, Janessa Klatt. Explore what's new in remote work and travel, including helpful tools and resources, need-to-know trends, destinations, and insight into what it really means to live and work around the world. 

    In this episode, Janessa reports back from a solo trip to a destination most travelers hesitate to visit alone, Caitlin shares a surprisingly simple tool for building calm and consistency into nomadic life, and both take a hard look at a habit nearly every long-term traveler has that might be doing more harm than good. There are also a few remote work stories from the community that prove people will go to remarkable lengths to keep living life on their own terms. 

    Have you ever talked yourself out of a destination based on what you'd heard, or found a way to build more balance into a life that never really stops moving? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message. 

    Tune In To Learn: 

    • Why Janessa says this distinction is one of the most important things solo travelers can internalize when traveling somewhere new 

    • How a single offhand comment on the podcast led Janessa to an unexpected scuba trip 

    • What solo travel in Egypt costs, why Cairo might not be your best nomad base, and what to consider instead 

    • A breathing technique that's worth adding to your daily routine while traveling 

    • Why you may want to create intentional seasons in your year even when the weather never changes 

    • The most committed remote work workarounds, and why it actually made sense  

    • And much more 

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    14 May 2026, 10:00 am
  • 1 hour 11 minutes
    Authentic Brazil: Off-the-Beaten-Path Adventure Travel with Gift of Go

    What if the part of Brazil most worth exploring is the one almost nobody talks about? 

    Eddie Lott is a Dallas-born expedition leader who has spent nearly two decades studying Brazilian history, geography, and culture. He rediscovered the Serra do Espinhaco in 2018 and has been documenting its trails and communities ever since. Elisa Oliveira is a Brazilian architect turned expedition coordinator who left behind her career and her previous life after a single weekend in the Espinhaco in 2019.  

    Together, they co-founded Gift of Go, a company that builds and leads founder-guided expeditions through one of Brazil's most layered and least-visited mountain ranges, and they are also husband and wife. 

    In this episode, co-host Paige McClanahan talks with Eddie and Elisa about how Gift of Go came to be, what their expeditions actually look like, and what travelers need to know before heading to this part of Brazil. 

    This is a rewarding listen for anyone drawn to real adventure travel in Brazil off the beaten path. Eddie and Elisa spent three-plus years walking the terrain, building relationships with local communities, and living in the region before guiding their first traveler. You'll hear why going deep into one place beats skimming across a whole country, how arriving somewhere by foot after 17 days on the trail completely changes how you experience it, and what it means to share a destination that still has almost zero international tourism presence. 

    Have you ever experienced a place that felt completely untouched by tourism? I'd love to hear about it, and I hope you'll share by sending me an audio message. 

    Co-host Paige McClanahan is a writer, editor, and former journalist based in Paris, France. As the author of The New Tourist: Waking up to the Power and Perils of Travel, Paige is passionate about making sure our travels have a positive impact on the world. Learn more about her work here. 

    Tune In To Learn: 

    • What makes the Espinhaco a microcosm of Brazil's most important ecological, cultural, and historical themes 

    • How Elisa left an engagement and a five-year architecture career after one weekend in a remote mountain village 

    • Why Gift of Go spent three years in the field before guiding their first traveler 

    • What the Veranico is, and why January might be the most spectacular and unpredictable time to visit 

    • How the expedition formats work, from 12-day group treks to fully bespoke solo journeys 

    • Why Brazil receives fewer international visitors per year than the city of Miami, and what that means for the right kind of traveler 

    • Practical tips for Minas Gerais: think in regions, know your biomes, expect limited English, and prepare for the warmth of the people 

    • What to eat and drink, from cachaça and UNESCO-recognized cheese to fig compotes with dulce de leche 

    • And so much more 

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    12 May 2026, 10:00 am
  • 1 hour 14 minutes
    The Goodness Game: 5 Rules to Pay It Forward with Small Acts of Kindness with Bryan Driscoll

    What if one small act of kindness could completely change someone’s life trajectory? 

    Bryan Driscoll is an entrepreneur, real estate investor, and the author of The Goodness Game. He built a multimillion-dollar real estate portfolio while running a marketing company, and he’s now focused on helping people create positive ripple effects through simple acts of kindness. 

    In this episode, Bryan shares the story that inspired his kindness philosophy and breaks down his five-rule framework for making the world better in a practical, sustainable way. 

    This episode offers a simple, practical way to approach kindness without overthinking it, something you can use at home or take with you on the road. Bryan breaks down how small, intentional actions can create meaningful impact, and why connection is often more valuable than money. It’s a grounded guide to taking action in a way that feels honest, natural, and aligned with your strengths, while also having a little fun. 

    What’s one small act of kindness you could commit to this week, even if it feels slightly uncomfortable? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message. 

    Tune In To Learn: 

    • Why a random act of kindness at age 18 changed Bryan’s life forever 

    • How the “Goodness Game” turns kindness into a simple daily practice 

    • Why giving without recognition creates a deeper impact 

    • How to identify your personal helping style and use your strengths 

    • Why not everyone is your “assignment” and how to stay in your lane 

    • How to avoid burnout when helping others by creating boundaries 

    • How Bryan used Craigslist to test the ripple effect of kindness 

    • Practical random acts of kindness ideas you can try this week 

    • Why overthinking stops people from helping and how to just start 

    • And so much more 

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    5 May 2026, 10:00 am
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