Episode 78: Adventure Has No Expiration Date with Beverly MacDowell


Adventure Has No Expiration Date with Beverly McDowell

What if some of your greatest adventures are still ahead of you?

In this episode of On Adventure, Josh sits down with Beverly McDowell, a retired educator, hiking guide, trail maintainer, and lifelong learner based in Asheville, North Carolina. She’s also the sister of actress Andie MacDowell – but Beverly has carved out an adventurous story entirely her own, much of it after age 50.

Beverly shares how hiking became a source of joy, confidence, community, and purpose, from introducing women over 60 to backpacking to maintaining sections of the Appalachian Trail. Along the way, she and Josh explore the beauty of Western North Carolina, the recovery following Hurricane Helene, the remarkable restoration of Max Patch, and why continuing to challenge ourselves physically and mentally becomes even more important as we age.

At the heart of the conversation is a simple reminder: you don’t have to take on crazy risks to become an adventurer. And you certainly don’t have to stop because you’re getting older.

🥾 In This Episode

  • 00:00 — Beverly’s unexpected second career as a hiking guide
  • 03:00 — Guiding visitors through Asheville and the Blue Ridge Mountains
  • 05:00 — George Vanderbilt’s lasting impact on Western North Carolina
  • 09:00 — Helping women over 60 experience backpacking
  • 13:00 — What first-time backpackers discover about themselves
  • 14:00 — Favorite destinations: the Smokies, Mount Mitchell, and 6,000-foot peaks
  • 17:00 — Hiking and tourism in Asheville after Hurricane Helene
  • 19:00 — How Max Patch recovered from being “over-loved”
  • 24:00 — Beverly’s favorite places to take first-time visitors
  • 30:00 — Why the mountains keep calling her back
  • 33:00 — Discovering camping at 36—and raising outdoor kids
  • 34:00 — Why it’s never too late to start hiking
  • 36:00 — Movement, balance, aging, and becoming more “antifragile”
  • 39:00 — Finding your own challenge and growth zone
  • 41:00 — Nature as meditation and an antidote to distraction
  • 44:00 — What outdoor experiences teach the next generation
  • 49:00 — Beverly’s search-and-rescue training and continuing desire to learn
  • 53:00 — The enduring lesson: adventure can begin at any age
  • 54:00 — How to connect with Beverly and hike with her

🌲 Key Takeaways

It’s not too late. Beverly didn’t begin camping until her 30s, joined the Carolina Mountain Club in her 50s, began maintaining the Appalachian Trail at 59, and started search-and-rescue training at 65.

A little challenge is good for us. Hiking asks the body and brain to constantly adapt—from navigating rocks and roots to maintaining balance—and Beverly believes those challenges become especially valuable as we age.

Guidance can turn intimidation into independence. By providing equipment, knowledge, safety, and community, Beverly has helped women over 60 discover that backpacking isn’t beyond their reach.

Nature restores more than the body. For Beverly, being outside is simultaneously exercise, meditation, education, and connection. As she puts it, getting outdoors is simply “a balm.”

Protecting wild places matters. From her trail-maintenance work at Max Patch to her love for Pisgah National Forest, Beverly’s story is also a reminder that the places that give us so much need something from us in return.

💬 Memorable Moments

“The majority of everything I did was post-50.”

“It’s a balm to get outside, to get your feet on the earth and walk.”

“A little challenge is good.”

“It makes you a completely badass grandmama.”

Connect with Beverly

Follow Bev McDowell on Facebook for Western North Carolina hiking, wildflowers, mushrooms, and outdoor adventures.

You can also find Beverly and request a guided half-day, full-day, or backpacking experience through Blue Ridge Hiking Company.

Whether your next adventure is a multi-day backpacking trip or simply walking a trail you’ve never explored before, Beverly’s message is worth carrying with you:

Start where you are. Keep moving. And don’t assume your best adventures are behind you.

Check out this episode!

On Adventure: Lessons from the Edge

Two recent conversations from the On Adventure Podcast – and what they have to say about the lives the rest of us are building.

Every so often we like to step back from the individual episodes and notice the thread running between them. The two most recent conversations on the On Adventure Podcast came from very different places – a bike-shop classroom on the California coast and a rotating string of mountain towns out West – and yet they landed in almost exactly the same spot. Both are about choosing the harder, fuller life on purpose, rather than drifting toward comfort or putting it off for some vague day down the road.

That turns out to be a financial question as much as an adventuring one. So here are the two, and a bit of what stayed with us.

Episode 75: Hard Things Are Worth Doing with Justin Smith

Justin Smith teaches high school in Santa Cruz, where his classroom is a working bike shop – teenagers learning to fix bikes, build résumés, and solve real problems with their own hands. On his own time, he’s an ultra-endurance athlete who has ridden the 2,700-mile Tour Divide from Banff to the Mexican border in sixteen straight days, raced the Fiji Eco-Challenge, and lined up at the Ironman World Championships in Kona.

What we appreciated most was how ordinary he made all of it sound. Justin talks about the “pain cave” – the dark hours before sunrise on day two of a race, when the body starts asking what exactly you’re doing out here – not as something to conquer but as a room you learn to redecorate and settle into. Comfort, he says, is what gets sold to us. Hard things are what actually move the needle. The line he repeats to his students and his daughter has stuck with us: a ship is safe in its harbor, but that is not what ships were built for.

Listen to Episode 75 →

Episode 76: Do It While You Can with Stefan Gruber

Stefan Gruber grew up in Raleigh, studied engineering at Western Carolina, and today works a remote job for a technology company he’s been with for about six years. But the more interesting thing about Stefan is what the remote job makes possible. Where a lot of us build our lives around our work, Stefan has quietly done the reverse – he’s built his work around the life he actually wants to live.

For the last couple of years, that life has been a moving target, in the best sense. When his wife Sarah began travel nursing, the two of them packed a car and a trailer and started following her contracts – Bozeman, where they later got married in Glacier; Idaho; and now Colorado Springs, in the shadow of the Garden of the Gods. Almost everywhere they land, there’s climbing within twenty minutes of the front door. Stefan describes climbing the way Josh describes the trail: one of the rare activities where you’re so locked into the next move that everything else – work, stress, the noise – simply melts away. He’s an unusually good photographer, too, a habit that started when he found an old camera lens in his parents’ attic and went looking for the camera to match it.

He was refreshingly honest about the cost. Living on the move means no steady circle of friends – the hardest part, he admitted, of the whole adventure. But when Josh asked him to boil it all down to one lesson, Stefan didn’t hesitate: get out and do these things while you can. We only live once, we’re a little older every day, and the experiences, he said, end up meaning more than any car or house ever could.

That’s a sentence we think about a lot on the financial side of the desk. The only real value of money is in its use – spending it on what’s genuinely of value to you, whatever your version of that is. It’s easy to spend a whole career building bigger buckets for a someday that keeps receding, only to arrive less healthy, less able, or not at all. Stefan’s life is a working argument for the alternative: decide what matters, and go live some of it now.

Listen to Episode 76 →

What We Took From Both

Put the two side by side and the lesson from the edge is really one lesson. The worthwhile life rarely happens by default. It gets chosen – on purpose, against the pull of comfort, and without waiting for permission or for the perfect moment that never quite arrives.

That’s the heart of how we think about planning, too. A good plan isn’t about the number for its own sake. It’s about being able to do the hard, meaningful things on purpose, to stay present through the long stretches, and to spend a life – not just save for one. We’re grateful to guides like Justin and Stefan for the reminder.

If either of these resonate, they’re worth a full listen. And if you’d like to talk through what you want your own version of “do it while you can” to look like, we’re here and happy to help.

Ridgeline Wealth Advisors

Episode 76: Summit Fever and Close Calls – Knowing When to Turn Back in the Mountains with Stefan Gruber


 

What happens when you build your work around the life you want to live?

In this episode of On Adventure, Josh talks with Stefan Gruber, a climber, photographer, traveler, and customer success professional at Levitate. Stefan shares how remote work and his wife Sarah’s career as a travel nurse have helped them create a life centered on movement, creativity, and outdoor adventure.

They discuss climbing, film photography, international travel, dangerous moments in the mountains, and the judgment required to turn around when conditions are not right. At the heart of the conversation is a simple message: meaningful experiences should not always be postponed.

In This Episode

  • Building a mobile life around remote work and travel nursing

  • Why climbing creates focus, presence, and flow

  • Traveling through the American West, Poland, and Nepal

  • The appeal of film photography and printed images

  • Balancing documentation with being present

  • Avalanche terrain, exposed climbing, and failed summit attempts

  • Summit fever, risk assessment, and the limits of luck

  • Future goals, including the Grand Teton and Colorado fourteeners

  • Why Stefan believes in doing things while you still can

Episode Chapters

00:00 – Colorado Springs and life on the move
Josh and Stefan discuss Colorado Springs, choosing temporary homes, and the possibility of eventually buying land in Colorado or Montana.

11:00 – Stefan’s career and lifestyle
Stefan explains how he moved from a long corporate commute into remote work and began traveling with Sarah during her nursing assignments.

17:30 – Climbing, travel, and flow
Stefan reflects on his Polish heritage, his early interest in travel, and the sense of complete focus he finds while climbing.

20:00 – Designing work around life
The conversation explores the freedom and tradeoffs of building a career that supports travel, adventure, and flexibility.

24:00 – Poland and international travel
Stefan describes Poland’s cities, mountains, coastline, affordability, and cultural growth, along with other memorable travel experiences.

36:30 – Photography and creative ambitions
Stefan explains how photography connects his travels and outdoor life. He also shares ideas for creating a travel channel with Sarah.

41:00 – Film, digital photography, and presence
They discuss the visual character of film, the value of printed photographs, and the tension between capturing an experience and fully living it.

51:00 – Risk, fear, and turning around
Stefan recounts dangerous moments involving avalanche terrain, exposed climbing, wildfire smoke, and two unsuccessful attempts on the Grand Teton.

57:00 – Summit fever and the limits of luck
The conversation turns to humility, decision-making, and why surviving a poor choice does not make it a good one.

1:04:00 – Survival psychology and photography advice
Stefan recommends Deep Survival by Laurence Gonzales and encourages new photographers to begin with whatever camera they can access.

1:11:00 – Favorite mountains and future goals
Stefan talks about the Tetons, Annapurna Base Camp, Denali, Everest, and his goals for the rest of 2026.

1:18:00 – Do it while you can
Stefan closes with his belief that health, time, and opportunity are uncertain, so meaningful goals should not always be saved for later.

Memorable Quotes

“Sometimes those limits find you.”

“There’s a certain store of luck, and it will run out eventually.”

“If it doesn’t happen today, it can happen another day.”

“Do it while you can.”

Key Takeaways

Build work around what matters.
Flexible work can create more room for travel, relationships, creativity, and meaningful experiences.

Turning around is not failure.
Good judgment sometimes means abandoning a climb or summit and returning under better conditions.

Luck is not a strategy.
A successful outcome does not automatically mean the decision behind it was wise.

Give photographs a life beyond the screen.
Printing images or shooting film can make photography feel more intentional and lasting.

Do not save everything for someday.
Adventure can be a major expedition or a small personal goal. The important step is beginning while the opportunity still exists.

Resources Mentioned

  • Deep Survival: Who Lives, Who Dies, and Why by Laurence Gonzales

  • Stefan’s Instagram page

About Stefan Gruber

Stefan Gruber is a climber, traveler, and photographer who works remotely for Levitate. He and his wife Sarah travel throughout the United States for her nursing assignments while pursuing hiking, climbing, skiing, photography, and international travel.

Keep Exploring

Subscribe to On Adventure in your podcast app and on YouTube for more conversations with people building meaningful lives through exploration, challenge, and curiosity.

Share this episode with someone who has been saving an important goal for “someday.”

Check out this episode!

Episode 75: Hard Things Are Worth Doing with Justin Smith


Episode Description
What happens in the dark hours before sunrise on day two, when your body starts asking
what exactly you are doing out here?
 
Justin Smith teaches high school in Santa Cruz, California, where his classroom is a working 
bike shop. By day he runs a Career Tech Ed program through Project Bike Tech, teaching
teenagers to fix bikes, build resumes, and solve real problems with their own hands. On his own
time, he is an ultra-endurance athlete who has finished the 2,700-mile Tour Divide from Banff,
Canada to the Mexico border in 16 days straight, raced the Fiji Eco-Challenge with Team Curl,
competed at the Ironman World Championships in Kona, and returned three times to a 60-hour
swimrun across the Swedish archipelago.
 
In this conversation, Justin takes Josh inside the pain cave and the mental game of multi-day 
racing: the dark hours before sunrise on day two, the difference between the front country and
the back country, and why the body only truly comes alive on the second night. He explains how
a psychology degree and Outward Bound canoe trips led to a life built around adventure, why he
and his wife once lived in a tiny house they built on television, and how putting himself in hard
situations makes him a better dad, husband, and teacher.
 
They also talk about the people. From trail angels on the Pacific Crest Trail to a septic-truck 
driver in Southern California, Justin keeps returning to the connections that outlast the miles.
Most of all, this is a story about a simple idea he repeats to his students and his daughter: a ship
is safe in its harbor, but that is not what ships were built for, and the more you do hard things,
the more you realize hard things are worth doing.
 
Episode Highlights
• 00:00 Meet Justin Smith: high school teacher by day, ultra-endurance adventurer on
his own time
• 02:00 The bike shop classroom and the Project Bike Tech program in Santa Cruz
• 08:00 Building a tiny house on the TV show Tiny House Nation
• 14:00 The permission slip to not conform, and choosing the hard path on purpose
• 16:00 Comfort is what gets sold to us, but hard things are what move the needle
• 19:00 Meeting Roy Malone at the 2019 Fiji Eco-Challenge with Team Curl
• 20:00 The One Water swimrun across the Swedish archipelago, attempted three times
• 26:00 The Stagecoach 400 and sleeping on McDonald’s cardboard with no sleeping bag
• 31:00 Courtney Dauwalter’s pain cave, and learning to redecorate it instead of fighting it
• 38:00 Finishing the 2,700-mile Tour Divide in 16 days, from Banff to the Mexico border
• 43:00 The Pacific Crest Trail, meeting his wife, and hiking through grief in 2009
• 55:00 Orienteering, gut instinct, and trusting intuition when the map runs out
• 01:04:00 A ship is safe in its harbor, but that is not what ships are built for
• 01:12:00 The mantra: if you can’t get out of it, get into it, and find a way

About Justin Smith

Justin Smith is a high school Career Tech Ed teacher in Santa Cruz, California, where he leads a
bike shop program through Project Bike Tech, and a lifelong endurance athlete and adventurer.
A former NCAA swimmer, he has finished the Tour Divide, raced the Fiji Eco-Challenge and
multiple expedition-style adventure races, competed at the Ironman World Championships in
Kona, and thru-hiked the Pacific Crest Trail. He lives in Santa Cruz with his wife and daughter,
with whom he shares most of his adventures.

Connect with Justin Smith
• Facebook: www.facebook.com/smilingjustin
• Inspire Out: www.instagram.com/inspireout/

Connect with the On Adventure Podcast
Hosted by Josh Self, financial advisor and everyday explorer.
• Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms
• Follow on Instagram for short-form clips and behind-the-scenes content
• Connect on Facebook: On Adventure Podcast with Josh Self
• Connect on LinkedIn: Josh Self
• If this episode resonated with you, leave a review and share it with someone who needs
to hear it.

Check out this episode!

On Adventure: What We Carry

Lessons from Gil Jackson and Aaron Saft

Every long walk is an exercise in deciding what matters enough to carry. Ounces add up over thousands of miles, and eventually you strip down to what is essential. In our two most recent On Adventure episodes, I sat down with a Cherokee language educator and an ultrarunning coach whose lives revolve around a version of that same question: out of everything you could hold onto, what is worth the weight?

Gil: Walking Home

Gil Jackson grew up in the Snowbird community of western North Carolina in the 1950s – no television, no car, one light bulb per room, and a tight-knit Cherokee community where everyone showed up when a neighbor needed help. When he left for college in Georgia, his mother laughed and said, “You’ll be back.” He was gone almost 40 years, then built a house 200 yards upstream from where he was born and poured himself into the work that now defines his days: keeping the Cherokee language alive.

Only about 130 fluent speakers remain, and they are losing roughly two and a half a month. Gil calls it the eleventh hour. He thru-hiked the Appalachian Trail in 2014 to experience some portion of what his ancestors endured on the Trail of Tears, and conceded the biggest difference: he got to come home. But what moved me most is what Gil does off the trail. He spends his days locating sacred Cherokee sites in the mountains and taking younger people to them, so the stories and routes are not lost. The elders who know where these places are can no longer reach them. The young people who can make the climb do not know they exist. Gil is the bridge.

Aaron: What Do You Need?

Aaron Saft has finished Hardrock, UTMB, Leadville, Western States, and the Bigfoot 200. But the moment from our conversation that will stay with me had nothing to do with a finish line. It was his description of what happens when you come across another runner sitting on a rock in the middle of a 100-miler. You do not ask, “How are you?” You can see how they are. You ask, “What do you need?” And then you give whatever you have. Aaron said it is not a decision people make in the moment. It is who the sport turns you into.

He pins an upside-down photo of his family to his quad so that when he looks down at mile 80, he sees his wife and kids looking back at him. His son now runs for the University of Portland. His daughter, a high school freshman, just competed at the state championships. When other parents ask how he got his kids into running, his answer is simple: he did not. He just showed them what was possible. He even rebranded his coaching business – from “MR Running Pains” to “Running is Life” – because the words we wrap around our work shape the experience. Training is 99 percent process and 1 percent celebration. If you cannot find joy in the process, you are missing the whole thing.

The Same Trail

Gil is preserving a language and the sacred geography of his people. Aaron is building runners who understand not just what to do but why. Both told me the point was never the miles. The miles were just the means of discovering what mattered enough to hold onto. Not every adventure happens on a trail. Some happen when you ask someone what they need and mean it, or when you pass along something that would disappear if you kept it to yourself.

Stay safe and stay on adventure.

— Josh

You can listen to the full conversations with Gil Jackson and Aaron Saft on the On Adventure podcast, available wherever you get your podcasts.

Episode 74: Carrying a Language Home with Gil Jackson


Episode 74: Carrying a Language Home with Gil Jackson

Episode Description

What does it mean to be so connected to a place that even your name carries it?
Gil Jackson, known by the Cherokee name Dohi, meaning outside or outdoors, was born in
Robbinsville, North Carolina in 1951 and today lives on 30 acres just 200 yards from the spot
where he came into the world. He is a fluent Cherokee speaker, one of roughly 130 left, an elder
of the Snowbird community, and an educator who has taught at Stanford, UNC Asheville, and
Duke. In 2014, he thru-hiked all 2,200 miles of the Appalachian Trail, walking in part to honor
his ancestors on the Trail of Tears.

In this conversation, Gil takes Josh inside a tight-knit upbringing built on Gadugi, the Cherokee
construct of community, where neighbors came together to cut wood, harvest crops, and care for
anyone in need. He explains why family kept him rooted in Western North Carolina even when
opportunity called him elsewhere, how a community school preserved the language while the
wider world pushed assimilation, and why Cherokee is considered one of the ten hardest
languages in the world.

They also talk about why Gil keeps walking. From a 48-mile day in the Great Smoky Mountains
to the ladder-strewn West Coast Trail on Vancouver Island, his adventures are less about
conquering anything and more about seeing the creator’s creation. Most of all, this is a story
about a race against time: preserving a language, the knowledge of medicinal plants, and the
sacred sites that risk being lost before the next generation can carry them forward.

Episode Highlights
• 00:00 A name that means outdoors, and a home built 200 yards from where he was
born

• 02:00 The Cherokee tradition of burying the umbilical cord to connect a child to the
land
• 05:00 Why family kept him rooted in Western North Carolina despite chances to leave
• 06:00 Growing up in 1950s Snowbird: one gravel road, one light bulb per room, no TV
• 08:00 Gadugi explained: the community coming together to help in times of need
• 13:00 An aunt’s middle-class home, new clothes, and the family that raised him
• 21:00 Selling moss for 25 cents a pound to buy a guitar he still owns
• 22:00 A community school that taught English while protecting the Cherokee language
• 24:00 Only about 130 fluent speakers left, and losing two and a half each month
• 27:00 What makes Cherokee one of the ten hardest languages in the world
• 29:00 Degrees in education, administration, and planning, and leading a language
immersion school
• 33:00 How Cherokee end-of-life traditions have changed over a lifetime
• 35:00 Finding the therapeutic in streams, trees, and birdsong
• 39:00 Why he thru-hiked the Appalachian Trail in 2014 to honor the Trail of Tears
• 43:00 The brutal West Coast Trail on Vancouver Island, with 100 ladders and 10 hours
for six miles
• 45:00 A tense night cooking near foraging bears in Virginia
• 46:00 A trail family of five speaking four languages, all wanting to learn Cherokee
• 53:00 Losing the knowledge of edible and medicinal plants, and the sacred sites that
hold the stories
• 57:00 Rapid-fire: Gvgeyu (I love you), favorite sunrises, beloved teachers, and the White
Mountains

About Gil Jackson
Gil Jackson (Dohi) is a fluent Cherokee speaker, elder of the Snowbird community in
Robbinsville, North Carolina, and a lifelong educator who has taught at Stanford, UNC
Asheville, and Duke and served as principal of a Cherokee language immersion school. He
remains committed to preserving the Cherokee language, traditional plant knowledge, and the
region’s sacred sites, and is an avid long-distance hiker who thru-hiked the Appalachian Trail in
2014.

Connect with the On Adventure Podcast
Hosted by Josh Self, financial advisor and everyday explorer.
• Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms
• Follow on Instagram for short-form clips and behind-the-scenes content

• Connect on Facebook: On Adventure Podcast with Josh Self
• Connect on LinkedIn: Josh Self
• If this episode resonated with you, leave a review and share it with someone who needs
to hear it

Check out this episode!

Episode 72: Risk in Every Form with Greg Winchester


ON ADVENTURE PODCAST |  EPISODE 72

Episode 72: Risk in Every Form with Greg Winchester

  

Episode Description

What does it take to keep saying yes to risk, in the boardroom, on the trail, and across all seven continents, for forty years and counting?

Greg Winchester calls himself an armchair explorer, but the title sells him short. Over a 40-plus-year career in commercial real estate, he has worked through the savings and loan crisis, the 2008 financial crisis, and COVID, first as a banker, then as a co-owner, and today as an investor through his family office, Summit Investors. In 2003, he and two partners bought their company from its founders in a management buyout, personally guaranteeing the entire debt with 300 employees and no safety net. As Greg puts it, it was like walking to the end of the diving board and jumping, hoping there was water below.

A lifelong Boy Scout who fell in love with the outdoors in the Roan Highlands of North Carolina, Greg went on to serve on the board of the Appalachian Trail Conservancy and to build a life of generosity that reaches all seven continents, inspired by the book Seven Summits. From an orphanage in Bolivia to a pastors’ training center in Uganda, a nearly thousand-year-old cathedral in Winchester, England, and Sir Ernest Shackleton’s grave on South Georgia Island near Antarctica, he and his wife set out to support smaller, lesser-known nonprofits and build real relationships, not just write checks.

In this conversation, Josh and Greg trace the many forms risk can take. They dig into why leverage is a two-edged sword, how diversification and dry powder let you run into the fire when others are running out, why your gut becomes a kind of superpower after twenty years in any arena, and how setting goals every year since his twenties shaped a life of purpose. Greg also shares the two questions a pair of mentors asked him in his mid-fifties, what is a noble cause you can get involved with, and what do you actually want to do, and why finishing well may be the greatest adventure of all.

Episode Highlights

         00:00  An armchair explorer who spent forty years navigating real estate’s biggest crises

         03:00  Stumbling into commercial real estate from a bank management trainee program

         06:00  The 2003 management buyout: 300 employees and everything personally guaranteed

         12:00  Jumping off the high dive and hoping there is water below

         14:00  A lucky break, a termination fee, and the real mix of hard work and luck

         17:00  Three things that get people in trouble: cycles, capital structure, and diversification

         20:00  Running into the fire in 2008 and why leverage is a two-edged sword

         23:00  The gut instinct you earn after twenty years in any arena

         25:00  Seven Summits and a vision to serve nonprofits on all seven continents

         29:00  Winchester Cathedral, a 950-year-old Bible, and Shackleton’s grave near Antarctica

         38:00  What rises to the top: relationships, faith, family, and friends

         40:00  A Boy Scout in the Roan Highlands and a lifelong love of the trail

         46:00  Moving toward something, not away, and setting goals every year since his twenties

         50:00  Finishing well and the two questions that reshaped Greg’s second act

Causes and Organizations Greg Supports

Here are the people and organizations Greg mentioned in this episode:

•    Summit Investors, his family office investing in real estate across the Sun Belt

•    Auburn University Master of Real Estate Development program, where he serves as an adjunct and industry connector

•    The Appalachian Trail Conservancy, where he served on the board

•    The South Georgia Heritage Trust, stewards of the historic church and museum on South Georgia Island

•    The National Christian Foundation, which helped guide his international giving

Free for Listeners: The Money Trail Guide

Josh’s free resource for everyday explorers is packed with practical insights on planning for any adventure, big or small, minimizing trail waste along the way (yes, that means taxes), and living with confidence toward whatever is most meaningful to you. It also includes key takeaways from recent On Adventure guests to help inspire your next steps.

Grab your copy at ridgelinewealthadvisors.com.

Connect with the On Adventure Podcast

Hosted by Josh Self, financial advisor and everyday explorer.

•    Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms

•    Follow on Instagram for short-form clips and behind-the-scenes content

•    Connect on Facebook: On Adventure Podcast with Josh Self

•    Connect on LinkedIn: Josh Self

•    If this episode resonated with you, leave a review and share it with someone who needs to hear it

Check out this episode!

Episode 71: Solo Female Travel, Real Risk, and the Belonging We All Crave with Amanda Black


ON ADVENTURE PODCAST | EPISODE 71

Episode 71: Solo Female Travel, Real Risk, and the Belonging We All Crave with Amanda Black

          

Episode Description

What does it actually take to step on a plane alone, head somewhere most people would call risky, and come home a different woman?

Amanda Black is the founder of the Solo Female Traveler Network, a community of more than half a million women that started as a small Facebook group during her expat years in Australia. Ten years and roughly thirty tours a year later, she leads women into places the average traveler tends to avoid: Egypt, Morocco, India, Mongolia, Uzbekistan, Kyrgyzstan, and beyond. Bali was the first trip. Seventeen women signed up. Nine of them ended up with the company logo tattooed by the end of it.

We talk about why she leans into destinations perceived as less safe, what real risk actually looks like versus the version we imagine, and why she pushes back on the idea that travel is simply safe or unsafe. Risk, she argues, is a spectrum and a muscle, and most women have a lot more capacity to build it than they have been told.

We also get into the quieter side of all this. The cobblestone cafe in Sighișoara, Romania, where women who had known each other only a few days started telling the truth about how lonely life back home really feels. The Golden Eagle Festival in Mongolia, where she felt like she had walked into a movie set with no electricity. The unexpected pattern she keeps noticing across every trip, every country, every group: people are not really upset about the hotel room. They want to belong.

Amanda also shares why she launched Kindred Community, a smaller, slower offering built around connection retreats in Southern California, and what almost a decade of leading women into the wild has taught her about courage, capability, and the kind of friendships that get a logo tattooed on someone’s wrist.

Episode Highlights

00:00  Welcoming Amanda Black, founder of the Solo Female Traveler Network

01:00  Building a community of 500,000+ women and running tours in 25 countries

03:00  Why she leans into destinations perceived as less safe: Egypt, Morocco, India, Mongolia, Uzbekistan, Kyrgyzstan

05:00  How strangers become a travel family inside the first 48 hours of a trip

08:00  From a Facebook group in Australia to a first Bali trip where 9 of 17 women got the company logo tattooed

12:00  Talking honestly with women about safety, fear, and the gray areas of real risk

15:00  Risk on a spectrum: why “safe or unsafe” is the wrong question, and how to build the muscle over time

17:00  Mongolia and the Golden Eagle Festival: stepping into a place that felt like going back in time

20:00  What solo travel reveals about how strong and capable women really are

22:00  The hidden business lesson behind a decade of tours: everybody just wants to belong

24:00  A cobblestone cafe in Sighișoara, Romania, and the loneliness that surfaces when women finally feel safe to share

27:00  Kindred Community and the next chapter: building belonging closer to home

Connect with Amanda Black

Bonus for Listeners (Free Travel Quiz):

https://thesolofemaletravelernetwork.com/where-should-i-travel-next-quiz/

The Solo Female Traveler Network

Website: thesolofemaletravelernetwork.com

Instagram: @solofemaletravel

TikTok: @sofetravel

YouTube: @sofetravel

Amanda’s TEDx Talk

Shared Firsts: Redesigning how we find belonging

youtube.com/watch?v=xSaVJH2b5H0

Amanda’s Website

meetamandablack.com

Kindred Community

Website: kindredcommunity.co

Instagram: @kindred.sd

Connect with the On Adventure Podcast

Hosted by Josh Self, financial advisor and everyday explorer.

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Episode 70: Saying Yes to the Right Invitations with Colin Stroud


ON ADVENTURE PODCAST  |  EPISODE 70

Episode 70: Saying Yes to the Right Invitations with Colin Stroud

                              

Episode Description

What if your next great adventure is not a destination at all, but a willingness to say yes to the breadcrumbs life keeps dropping in front of you?

Colin Stroud is a 26-year-old credit card rewards consultant, founder of Go Somewhere, and one of the fastest growing voices on LinkedIn in the points and miles space. He grew up in Fort Wayne, Indiana, the son of an OB/GYN and a nurse midwife who met delivering a baby together, and he was on track for a more traditional path until a six-week Spanish immersion trip to Oviedo at 16 cracked the world wide open. From there it was Italy on a $380 flight, a Catholic mission to Poland, an unlikely run at Ave Maria University in south Florida, an early marriage and a baby on the way before he had even graduated, and a first job in life insurance case design that he knew almost immediately was not it.

What followed is a story about paying attention. A coworker mentioned the Chase Trifecta. A LinkedIn post about points went viral and got picked up by The Washington Post. A side hustle turned into consulting calls, then into a community for business owners, then into a full-time business helping families and entrepreneurs unlock travel they thought they could not afford.

We talk about why early travel rewires you, what it actually takes to leave a steady paycheck, the difference between dopamine and meaning, why family life and entrepreneurship feel like the truest adventures of his life right now, and the surprising decision he and his wife made after almost moving to Hawaii. Colin makes a strong case that the go somewhere life is not always about getting on a plane, and that learning to be rooted where your feet are can be its own kind of expedition.

 

Episode Highlights

00:00  From cheap flights as a teenager to a full-time business helping people unlock travel

06:00  World Youth Day in Poland, six weeks of Spanish immersion in Oviedo, and catching the travel bug

14:00  Marriage, a baby on the way, and a first job in life insurance that did not fit

18:00  Discovering the Chase Trifecta and stepping into the points world

23:00  The first viral LinkedIn post and a Washington Post quote that changed everything

25:00  Quitting in November 2024 and going full-time on Go Somewhere

30:00  Almost moving to Hawaii, pumping the brakes, and rethinking what travel does for young kids

34:00  Why family life and entrepreneurship are the truest adventures of his life right now

39:00  Measuring yourself: finally finding feedback after years of feeling stuck

47:00  The two ingredients behind a viable internet business: clear writing and consistent humility

55:00 What adventure means now and where to find Colin online

 

Connect with Colin Stroud

LinkedIn: linkedin.com/in/colinstroud

Website: gosomewhere.world

Newsletter: The Go Somewhere Newsletter at gosomewhere.world

Email:

 

Connect with the On Adventure Podcast

Hosted by Josh Self, financial advisor and everyday explorer.

Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms

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Subscribe to the Patreon for more content!

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Check out this episode!

Episode 69: No One Was Waiting at the Finish Line with Madison Blagden


ON ADVENTURE PODCAST  |  EPISODE 69

Episode 69: No One Was Waiting at the Finish Line with Madison Blagden

 

   

   

Episode Description

What would it take to walk 10,000 miles in a single calendar year? Not across a lifetime. Not spread over a decade. One year.

Madison Blagden is a long-distance hiker and content creator from Massachusetts who went from a pre-med student with zero backpacking experience to one of the most prolific endurance hikers in the country. After completing the full PCT (2022), the Eastern Continental Trail from Key West to Newfoundland (2023), and the Continental Divide Trail (2024), she did all three Triple Crown trails back to back in 2025, border to border, logging over 10,000 miles in a single calendar year. She documented every step herself through daily YouTube videos, Instagram shorts, and blog posts, all edited on the road.

Starting in the Florida Keys in January, she pushed through Hurricane Helene damage on the AT, Sierra snowpack, desert heat, a debilitating hip injury in the White Mountains, and a flash flood that hit her tent in the middle of the night in the desert. The miles are extraordinary. But this conversation goes deeper than the miles.

We talk about what happens between the ears when the body wants to quit, the difference between healthy internal ambition and ego-driven achievement, how the most meaningful finish lines are the ones where nobody is waiting for you, what a flash flood teaches you about calm under pressure, the spiritual dimension of pushing past absolute exhaustion, and why you will never be 100 percent ready, and that is not a reason to wait.

 

Episode Highlights

•       00:00  Introduction: Walking 10,000 miles in one calendar year

•       02:00  Madison’s background: pre-med to PCT with no backpacking experience

•       04:00  Van life, COVID, and two years of traveling in a 19-foot RV

•       09:00  Comparing the AT, PCT, and CDT: terrain, culture, and difficulty

•       14:00  Hurricane Helene’s impact on the Appalachian Trail and trail recovery

•       19:00  Planning a 10,000-mile year: budget, timing, and keeping it flexible

•       24:00  How a 5,600-mile year sparked the idea to go even further

•       31:00  Funding the hike through daily content creation on the road

•       34:00  Healthy ambition vs. ego-driven achievement

•       39:00  Internal motivation: the David Goggins voice and the gentle encouragement

•       42:00  37 miles a day for nine weeks: the math behind finishing the CDT before snow

•       48:00  Hip injury in the White Mountains and the lesson in letting go

•       51:00  Flash flood survival and what it reveals about fight-or-flight

•       57:00  Nervous system training and calm under pressure

•       01:02:00  Surrendering control: giving it up to the trail and the universe

•       01:05:00  Spiritual experiences that emerge only at the edge of physical exhaustion

•       01:10:00  Coming off trail softer: how big accomplishments quiet the ego

•       01:15:00  Closing encouragement: you will never be 100 percent ready, so go

•       01:20:00  The expanding ceiling of human limits and what comes next for Madison

 

Connect with Madison Blagden

Instagram & YouTube: @madisonblagden

Website: madisonblagden.com

Substack: substack.com/@madisonblagden

The Trek: thetrek.co/author/madison-blagden

 

Connect with the On Adventure Podcast

Hosted by Josh Self, financial advisor and everyday explorer.

•       Subscribe on YouTube, Spotify, Apple Podcasts, and all major streaming platforms

•       Follow on Instagram for short-form clips and behind-the-scenes content

•       Connect on Facebook: On Adventure Podcast with Josh Self

•       Connect on LinkedIn: Josh Self

•       If this episode resonated with you, leave a review and share it with someone who needs to hear it

Check out this episode!