What do you do when the only way out of the country during a pandemic is to advertise yourself on a Facebook sailing group and hope someone takes you?

If you're Matt Whitley, you pack your bags, fly to Spain, and spend 21 days crossing the Atlantic with a family you'd met on one 20 minute call.

Matt is a 23 year old adventurer from South Manchester quietly living a life most people only dream about. At 19, with COVID shutting every door, he hitchhiked onto sailing boats across the Atlantic, worked in the Amazon jungle, and sailed the Caribbean before making it back just in time for university. Fresh out of graduation, he flew his bike to Vietnam with nothing but dots on Google Maps, and spent a year cycling through Vietnam, China, the Tibetan Plateau, Mongolia, and Central Asia, roughly 100km a day.

In this episode, we cover his bike completely breaking down in the middle of the Tibetan Plateau and how he got himself out of it, a stranger he met at a frozen mountain lake whom he never expected to encounter, a 5:30am wake-up call in Mongolia that turned into one of the scariest moments of the trip, and how he pulled off a year like this with barely any plan at all.

We also go deep on privilege, what it means to be born in the global north, why the poorest countries on his route made him feel the most welcomed, and what to actually do with that beyond feeling guilty.

This episode is for anyone who has talked themselves out of the thing they actually want to do, or wondered if the world is as scary as it looks. Spoiler: it's not. Matt is living proof. This is Part 1. Part 2 is coming, and it's the one that stops people in their tracks. Stay close!

Connect with Matt:

• Instagram
• Fund a kitchen in Gaza

Follow along on other platforms:

• Instagram

~ KEYWORDS: bikepacking Vietnam to UK, solo cycling Central Asia, cycling the Tibetan Plateau, bike touring Afghanistan, sailing across the Atlantic Ocean, hitchhiking on sailing boats, crossing the Amazon rainforest by boat, adventure travel podcast, cycling Pakistan mountains, solo travel fear and courage, charity water fundraiser run, global privilege and travel perspective, bikepacking route planning tips, Suriname sailing adventure, Mongolia cycling trip, extreme endurance challenges, long distance cycling gear and logistics, travel storytelling podcast, backpacker life lessons, gap year adventure travel, cycling through China, Kyrgyzstan travel story, sailing the Caribbean, ultra marathon training, run club culture, digital nomad travel podcast, world travel and humility, dangerous travel encounters, global south vs global north, meaningful travel experiences, van life and camping on the road, cultural immersion travel stories, remote adventure cycling, travel and mental resilience

What happens when a 23-year-old, unemployed and fresh out of university during Portugal's worst financial crisis, decides to start his own surf camp anyway?

In this episode, David Moore shares the story of building Surf Cascais from the ground up into one of Portugal's most loved surf schools, surf camps, and surf villas. I had the absolute pleasure of staying at Surf Cascais while recording this conversation, and can say firsthand that the community David has created is truly something special.

David opens up about growing up in Lisbon completely obsessed with surfing, catching his first waves at 13, and how a lifelong passion for surfing slowly turned into a business he never set out to build. He shares the mentor who changed everything, the mindset that carried him through his early 20s with zero plan B, and why Cascais might be one of the most underrated surf towns in Europe.

We also talk about what it really takes to build a business rooted in connection rather than hustle. Now 13 years into running Surf Cascais, David spills the real secret to running a successful surf camp, the one belief that has driven every decision he's ever made, and his newest project taking the Surf Cascais community around the world.

This conversation is for anyone curious about starting a business from scratch, what it really takes to build a successful surf camp, or daring to leave the traditional path behind and build a life around the thing you love most.

Connect with David & Surf Cascais:

Book your stay → surfcascais.com

Instagram → @surf.cascais

Surf Atlas (small-group surf trips worldwide, via Surf Cascais) @surfatlas.co

David on LinkedIn → David Moore Rodrigues dos Santos

Surf Cascais Video Linked Here.

Follow along on other platforms:

• Instagram
• Tiktok
• Youtube

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KEYWORDS

surf cascais, david moore surf cascais, surf camp portugal, surf school cascais, how to start a surf camp, starting a business in your 20s, guincho beach surf, carcavelos surf, praia grande surf, surf villa portugal, surf atlas, maldives surf trip, lisbon surf camp, move to portugal, learn to surf portugal, solo travel portugal, kindred roads podcast, mary goggin podcast, unconventional life podcast, solo travel podcast

What happens when two friends invite a man they met outside a Little Caesars to come live with them, and all three of their lives change forever?

This one is a little different from our usual episodes, but it might be the most important kind of story this podcast was made for.

In this episode, Josh and Chandler share the story of how they met Trevor, a man who had been living on the streets, and what unfolded when they opened their home to him. We invited Trevor to join this conversation and share his own story, and while he could not make it, his presence is woven into every part of it.

Josh and Chandler talk about the months of showing up before Trevor ever moved in, the laughter and the hard conversations, and how what started as wanting to help someone turned into one of the most meaningful friendships any of them have ever had. They get into the spontaneous trip to New York where Trevor received something he had dreamed about for years, the ways Trevor has healed parts of them they did not expect, and how he is already inspiring others simply by being himself.

This conversation also goes deep on the biggest misconceptions people carry about the homeless community, why money and housing alone rarely create lasting change, and the vision Josh and Chandler are building through the Good Intentions Club to help more people the way Trevor has helped them.

It is a powerful reminder that when you show up for someone, you never know how much they will end up showing up for you too.

Connect with Josh and Chandler:

• Chandler's Instagram
• Josh's Instagram
• Good Intentions Club Products
• Help Get Trevor His Van

Follow along on other platforms:

• Instagram
• TikTok

homelessness, homeless community, helping the homeless, kindness, human connection, community, Good Intentions Club, misconceptions about homelessness, changing lives, friendship, giving back, mental health, loneliness, healing, unconventional life, hope, generosity, paying it forward, servant leadership, social impact, acts of kindness, faith in humanity, inspiring stories, purpose driven life, making a difference

What happens when a solo woman decides to cross continents by bicycle, trusting the kindness of strangers along the way?

In this episode, Claire Wyatt shares the story of cycling across some of the most remote places on earth. From riding thousands of miles across Mongolia to cycling from Asia to the UK, Claire built a life on the road powered by curiosity, resilience, and the generosity of people she had never met before.

Claire talks about navigating long stretches of wilderness, crossing rivers in Mongolia, cycling through Central Asia, and riding parts of the Pamir Highway. Along the way she experienced countless moments of unexpected kindness, from families inviting her into their homes to strangers helping when the road became difficult.

We also talk about what it really takes to live this kind of unconventional life. Claire shares how she prepared for long distance cycling, the mental challenges of traveling alone for months at a time, and what she learned about trust, independence, and human connection along the way.

This conversation is for anyone curious about long distance cycling, solo female adventure travel, or what happens when you step far outside the normal path and discover how supportive the world can actually be.

Let’s dive in!

Connect with Claire:

• Instagram
• Biking Guide Coming Soon (Message me in the meantime if you'd like it)!

Follow along on other platforms:

• Instagram
• Tiktok
• Youtube

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KEYWORDS

solo female cyclist, cycling across Mongolia, Mongolia to UK cycling journey, solo female travel adventure, long distance bicycle touring, bikepacking Central Asia, Pamir Highway cycling, cycling across continents, kindness of strangers travel stories, women adventure travel, solo female adventure travel, bicycle touring inspiration, cycling the Silk Road route, extreme bikepacking journey, female cyclist world travel

What happens when you leave a stable 9 to 5 and decide to build a career around your passions instead?

In this episode, Olivia Chenery, a London based events, hotel, fashion, and brand photographer, shares how she walked away from corporate life and built a photography career. What started as small shoots and saying yes to opportunities before she felt fully ready turned into photographing Morgan Riddle, a major influencer at Wimbledon, and working with brands and hotels across the UK and the world.

Olivia talks about the fear of losing financial stability, the pressure of starting over, and the steps she took to turn photography into a full time career. She shares how she found her first clients, how she built her portfolio, and how she positioned herself in competitive industries like fashion, hotels, events, and brand photography in London.

We also talk about her solo trip to Portugal and how traveling alone helped her grow creatively and personally.

This episode is for anyone who feels stuck in a 9 to 5 but is scared to leave. It is about taking a creative risk, building something from scratch, and understanding what it actually takes to make photography a real career. Let’s dive in!

Connect with Olivia:

• Website
• Instagram

Follow along on other platforms:

• Instagram
• Tiktok
• Youtube

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KEYWORDS Olivia Chenery, London photographer, London fashion photographer, London events photographer, London hotel photographer, brand photographer London, how to become a photographer, leaving your 9 to 5 job, quit your corporate job for photography, creative career change, full time photographer journey, how to start a photography business, beginner photography tips, building a photography portfolio, finding your first photography clients, freelance photographer London, female photographer London, travel photography Portugal, solo travel Portugal, creative entrepreneurship, turning your passion into a career, how to grow as a photographer, photography business advice, starting over in your twenties, leaving a safe job for a creative career, photography industry insights

What happens when two travelers leave everything familiar behind and cross the Middle East on foot and by camel, following a path few Westerners have ever taken?

In this episode, Wells Jones shares the story of a 1,100 mile trek across Saudi Arabia, Jordan, and Syria, retracing the route of T.E. Lawrence through deserts, border crossings, and remote communities, alongside his close friend Miles. What he expected to find was tension and danger. What he found instead was something far more complex, moments of uncertainty paired with unexpected kindness, generosity, and deep humanity.

Wells talks about riding camels through Wadi Rum, navigating intense checkpoints, preparing for real risk, and learning how listening and humility opened doors that fear never could. This conversation explores long distance travel in politically complex regions, cultural respect, trust, and what happens when you let curiosity lead instead of assumptions.

It is a powerful reminder that the world is often more human than we are taught to believe.

Connect with Wells:

• Purchase His Book, A Line in the Sand
• Connect on Linkedin
• Kayak for a Cause

Follow along on other platforms:

• Instagram
• Tiktok
• Youtube

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KEYWORDS

Middle East trek, 1,100 mile journey, desert expedition, camels, cultural understanding, T.E. Lawrence, long distance travel, humanity and travel, middle east travel

Max Campbell is sailing around the world on a 50 year old Swan 37 named Elixir, a boat he rebuilt by hand and turned into a fully functioning home at sea. Over the past few years, he has sailed from the UK to New Zealand with an ever changing crew, navigating open ocean crossings, remote coastlines, and places that can only be reached by boat.

In this episode, Max walks us through the moments that defined his journey. He shares the story of being caught on fire during a solo Atlantic crossing, then sailing alone for two more days with serious burns to reach land. He explains what daily life actually looks like at sea, how it feels to be disconnected for weeks at a time, and why that level of isolation can bring clarity rather than fear.

We also dive into experiences that still feel hard to believe, such as being boarded off the coast of Venezuela, spending time in an immigration jail in southern Mexico, listening to firsthand stories from people who crossed the Darien Gap, and reaching South Pacific islands where boats are the only way in and trading supplies for food is still part of everyday life. This conversation is raw, eye opening, and deeply human, and it offers a rare look at what it really means to live at the edge of the world.

Let’s dive in!

Connect with Max and follow the journey below:

• Instagram
• Youtube
• Tiktok
• Website
• Patreon Sailing Crew
• About Elixir and the Crew

Follow along on other platforms:

• Instagram
• Tiktok
• Youtube

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KEYWORDS

Max Campbell, Untide, un tide, Elixir sailboat, Swan 37, sailing around the world, circumnavigation, solo Atlantic crossing, Atlantic crossing fire, boat fire accident, ocean sailing crew, sailing New Zealand, South Pacific remote islands, being boarded at sea, Venezuela coast guard boarding, piracy at sea story, Mexico immigration jail, Tapachula detention center, Darien Gap stories, sailing content creator

Natalie Ng is a videographer and writer from Perth, Australia who spent 20 months traveling the world alone. She did not leave with everything figured out. She left with questions, curiosity, and a willingness to learn as she went.

In this episode, Natalie talks honestly about what it was like to travel solo as a woman for the first time. She walks through the fears she had before leaving, how she approached safety on the road, and how she handled the concerns and expectations of family back home. She shares the practical ways she built confidence over time, learned to trust her instincts, and made decisions that kept her grounded while constantly moving.

We also talk about the places that shaped her experience most, including time in Italy, the Balkans, Morocco, Nepal, and Southeast Asia. Natalie shares stories from trekking to Annapurna Base Camp, volunteering in Nepal, navigating different cultures as a solo woman, and learning when to slow down instead of rushing to the next place.

This conversation is for women who want to travel alone but feel unsure about safety, judgment, or not knowing where to start. It is an honest look at long term solo female travel, what actually helps, what matters most, and why you do not need a perfect plan to begin. Let’s dive in!

Connect with Natalie:

• Website
• Shop Her Prints
• Read Her Blogs
• Instagram

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Follow along on other platforms:

• Instagram
• Tiktok
• Youtube

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KEYWORDS