Zero To Travel Podcast

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 

Resources: 


Sign up for our FREE newsletter 


Blake’s website 


Dirtbag Rich book 


Unschool Adventures 

Want More? 


The Vagabond's Way: Meditations on Wanderlust, Discovery, and the Art of Travel w/ Rolf Potts  


The 5 Best Hacks of “All the Hacks”: Travel, Money & Life Optimization with Chris Hutchins 


Digital Detox: Downsizing Your Digital Life to Create Freedom + Reboot Your Lifestyle Business with Corbett Barr 

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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 

Resources: 


Sign up for our FREE newsletter 


Work From Uruguay 


Instagram 

Want More? 


Building a Travel Lifestyle: Digital Nomadism, Slow Travel, Exploring Latin America with Kyle Cohenour 


From Expat to Digital Nomad: Finding Your Travel Rhythm, Balancing Burnout, and the Digital Nomad Lifestyle with Kristin Wilson 


Creating A Life Abroad + Expert Remote Work Advice with Chase Warrington 

Thanks To Our Sponsors 


Become a Fora Advisor today at foratravel.com/zerototravel 


Check out Morning Brew Daily for business news that's actually fun. 

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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 

Resources: 


Sign up for our FREE newsletter 


Tom’s website 


The World Walk book 


Microadventures book 

Want More? 


Walking the World with Alexander Campbell and Tom Turcich 


The World Walk (Trilogy): Lessons From A 7 Year Walk Around The World w/ Tom Turcich 


Exploring A Single Map: A Travel Adventure For Everyone With Alastair Humphreys 

Thanks To Our Sponsors 


Become a Fora Advisor today at foratravel.com/zerototravel 


Check out Morning Brew Daily for business news that's actually fun. 

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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 

Resources: 


Sign up for our FREE newsletter 


My Most Authentic Life 


Instagram 


The Perfect Average Day 


Laundry House 

Want More? 


How to Pivot to a Life With More Freedom (And Travel), Get More Free Time, and Unlock Your Intuition With Jenny Blake 


How to Navigate Transitions and Design Your Life (Without the BS) with Lauren Handel Zander 


Two Paths to Location Independence and Travel (No Skills Required) With Caitlin Sunderland and Janessa Klatt 

Thanks To Our Sponsors 


Become a Fora Advisor today at foratravel.com/zerototravel 


Get 20% of at Cozy Earth with code ‘TRAVEL’ 

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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 

Resources: 


Sign up for our FREE newsletter 


Goats On The Road 


Hash House Harriers 

Want More? 


Transition to Travel: From Burnout to a Year Around the World with Sofia and Teague 


Building a Travel Lifestyle: Digital Nomadism, Slow Travel, Exploring Latin America with Kyle Cohenour 


The Reality of Digital Nomad Life (Warts and All) With Steph and Dalt 

Thanks To Our Sponsors 


Become a Fora Advisor today at foratravel.com/zerototravel 


Get 20% of at Cozy Earth with code ‘TRAVEL’ 

Learn more about your ad choices. Visit megaphone.fm/adchoices