Episode 52: Skydiving Everest, High Mountain Summits and Empowering Female Rangers with Holly Budge


In this special episode of the On Adventure Podcast, I sit down with the unstoppable Holly Budge—an adventurer, conservationist, and the first woman to skydive over Mount Everest. With World Female Ranger Week in full swing, this conversation couldn’t be more timely. You can find out more about what these incredibly brave female rangers do here and why they are being celebrated this week.  Holly opens up about transforming fear into fuel, climbing the world’s highest peak solo, and how her bold expeditions became a platform for championing female wildlife rangers.

We explore her work with How Many Elephants and the founding of World Female Ranger Week, diving into the challenges and triumphs of the women on the front lines of conservation. Whether you’re an adventure junkie, a purpose-driven leader, or someone looking for that next spark of inspiration, this episode delivers the goods.

Timeline Summary:

[2:15] – How a single conversation launched Holly’s journey to skydive Everest
[6:47] – What it’s like to freefall at 29,500 feet over the Himalayas
[12:22] – Training your mindset for mental toughness and high-altitude endurance
[17:31] – The origin story of How Many Elephants and connecting passion with purpose
[21:18] – Launching World Female Ranger Week and elevating unheard voices
[27:05] – Grit, resilience, and the power of women protecting the wild
[35:40] – What Holly’s adventures have taught her about life and leadership

Links & Resources:

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What the Everyday Explorers of the On Adventure Podcast Have Taught Me About Making a Good Life Great

You have a solid job that covers the essentials and taps into your talents. Your relationships with your spouse, children, extended family, and close friends are meaningful and enriching. Your home offers both comfort and safety, and your golf outings or local volunteer work add enjoyable dimensions to your routine.

On paper, you’re living the ideal life. Yet many who tick these boxes still feel there’s a gap—something intangible yet deeply felt.

Recently, a compelling study published in Affective Science explored exactly what constitutes a truly “good life.” Researchers surveyed nearly 4,000 individuals from nine countries, including the U.S., asking participants to envision their ideal lives and rank various descriptors reflecting happiness, meaning, and psychological richness.

Happiness as the Foundation

The study identified foundational happiness with descriptors like:

  • Stable
  • Comfortable
  • Simple
  • Happy
  • Pleasant

This is your baseline. Achieving this level of happiness means your basic emotional and physical needs are met. From here, you have the stability and clarity needed to expand your life in meaningful ways.

Adding Layers of Meaning

The next dimension is meaning, expressed through terms such as:

  • Meaningful
  • Fulfilling
  • Virtuous
  • Sense of purpose
  • Involves devotion

This aligns perfectly with the conversations we have on the On Adventure podcast, highlighting individuals who choose purpose over mere comfort. Whether through meaningful work, volunteerism, or mentoring, creating a life of purpose enriches your emotional experience and builds a legacy.

As I’ve discussed frequently on the podcast, meaning becomes even more critical during life’s transitions, especially retirement. Those who pursue meaningful work or passions tend to continue finding fulfillment long after their career concludes.

Embracing Psychological Richness

Perhaps most intriguing—and closely related to our ongoing discussions on adventure—is the third dimension: psychological richness, characterized by:

  • Eventful
  • Dramatic
  • Interesting
  • Full of surprise
  • Psychologically rich

Adventure inherently creates psychological richness. It involves challenge, uncertainty, overcoming obstacles, and embracing curiosity. It keeps you from stagnation and boredom. Guests on the On Adventure podcast consistently affirm that embracing adventure dramatically enriches their lives, offering insights, perspective shifts, and growth opportunities they never anticipated.

The interplay between happiness, meaning, and psychological richness evolves as you journey through life. Adventure, in various forms, ensures that you continuously grow and remain energized.

So how do we balance these elements effectively, especially as our lives change over time? That’s where Life-Centered Planning comes into play—helping you strategically align your resources with the kind of life that genuinely excites and fulfills you right now. Let’s explore together how your personal adventure can guide the design of your great life right now!

Episode 51: The Journey to Ultra – Why Endurance Athletes Need a Strong Mind and Stronger Community with Jess Hanson


In this episode of On Adventure, I sit down with Jess Hanson—a certified mental performance consultant, ultra runner, and coach—to explore what it takes to build a resilient mindset for both high-performance athletes and everyday adventurers. Jess shares her journey from playing lacrosse in college to coaching athletes across sports like skiing, mountain biking, and ultra running. We dive deep into how the mental game shapes athletic success, and how pushing your physical and emotional limits can unlock deeper purpose, confidence, and grit.

If you’ve ever faced the “dark moments” in endurance sports or wondered how to mentally prepare for big goals, this conversation is for you. We talk about identity, risk, motivation, and what it really takes to show up when things get hard. Plus, Jess gives us a behind-the-scenes look at her own ultra journey – yes, even the gritty details of 100K races, helicopter skiing, and rim-to-rim-to-rim Grand Canyon adventures.

⏱️ Timeline Summary

  • [1:20] – From lacrosse to ultra running: Jess shares her athletic evolution

  • [4:45] – Why mental performance matters—and how it’s different from traditional coaching

  • [11:40] – Facing fear in the backcountry and building confidence in uncertain moments

  • [16:50] – Running her first 50-miler with just two months of training (!)

  • [21:55] – Mental spirals and self-talk strategies during her 100K trail race

  • [33:10] – Why she loves working with high school athletes and how she helps them reshape their relationship with sport

  • [45:10] – What drives Jess to keep pushing her limits in running, skiing, and life

🔗 Links & Resources

💬 Closing Thoughts

If this episode gave you fuel to keep chasing your goals – or gave you tools for when the trail gets tough – please rate, follow, and share On Adventure. Also find us on our new YouTube page and click to subscribe!  And if you haven’t yet, go back and check out Episode 36 with Jess’s dad, Scott Hanson, for more inspiring stories from the trail.

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Episode 50: What My Son Taught Me About True Strength and Courage with Hudson Self


In this heartfelt episode of the On Adventure Podcast, I sit down with a younger Everyday Explorer, my son Hudson, for a conversation that redefines what adventure truly means. While we often explore tales of physical challenge and bold travel, this episode takes us on an inward journey—a story of persistence, identity, and the courage to live fully despite daily challenges. Hudson lives with Prader-Willi Syndrome (PWS), a rare genetic condition, and he brings us into his world with sincerity, wisdom, and humor.

We talk about what it’s like to grow up with PWS, the unique joys and struggles that come with it, and how it’s shaped Hudson’s perspective on life. He shares how adventure isn’t just found on mountaintops or across oceans—it’s in the relationships we build, the obstacles we face, and the love we share. From exploring WWII history in Europe to dreaming about the Great Wall of China, Hudson reminds us that the truest adventures are often the ones that take place in our own hearts and homes. This episode is not just a story of difference—it’s a story of belonging, resilience, and the extraordinary power of being seen and included.

⏱️ Timeline Summary

  • [0:00] – Meet Hudson Self and an introduction to Prader-Willi Syndrome Awareness Month

  • [1:00] – Hudson’s heartfelt presentation on living with PWS

  • [3:00] – Sharing his passions and personal joys beyond the diagnosis

  • [5:00] – The importance of inclusion and being treated like everyone else

  • [7:00] – Discussing the constant challenge of hunger with PWS

  • [9:00] – How PWS brought meaningful relationships and mentors into Hudson’s life

  • [10:00] – Visiting historical sites in Europe and the emotional impact of Normandy

  • [12:00] – Dreaming of a future adventure to the Great Wall of China

  • [13:00] – Favorite memories from a Jurassic-themed trip to Hawaii

🔗 Links & Resources

🎧 Closing Thoughts

This episode is a powerful reminder that adventure comes in many forms. If Hudson’s story moved you, inspired you, or made you think a little differently, please consider rating, following, and sharing the podcast from our YouTube (this is brand new!), Instagram and Facebook pages (this is new too!). And don’t forget to leave a review—we’d love to hear from you.

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Episode 48: Beautiful rebellion and choosing creativity over conformity with Thad Cockrell


In this episode of the On Adventure Podcast, I sit down with singer-songwriter and creative visionary Thad Cockrell for a conversation that took an unexpected but deeply inspiring turn. Thad opens up about his journey from wrestling mats and seminary halls to Nashville stages and international acclaim—all while forging a career based on creativity, authenticity, and saying a bold “yes” to uncertainty. We explore what it means to create from love rather than fear, and how rebellion, doubt, and wonder can be sacred tools on the creative path.

From Thad’s bold decision to sell his album for $100 directly to fans, to the moment Jimmy Fallon discovered his song in a hardware store, this conversation will challenge the way you think about success, security, and what it means to truly create without an agenda. Whether you’re an artist, entrepreneur, or just someone seeking a more intentional life, this episode is packed with insight and soul.

⏱️ Timeline Summary:

[1:45] – Thad on how creativity is a daily act of defeating doubt
[4:00] – Why you can’t conform and create at the same time
[9:55] – The childhood moment that sparked Thad’s unexpected path toward music
[14:20] – Discovering Neil Young and realizing, “This is what I’m supposed to do”
[24:30] – Moving to Nashville and the wild story of unexpected community support
[33:50] – Thad’s transformative shift from insecurity to creating from security
[44:00] – How he released his latest album for $100 and made more than 13 years on Spotify
[49:50] – What it means to create from the present moment with no need for external validation
[56:00] – Thad’s big dream: building a new music economy and going platinum without streaming

🔗 Links & Resources:

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Episode 47: Suffering together with Patrick Serfass


Some stories grab you right from the first sentence—and this one, with Patrick Serfass, took me on a ride I didn’t want to end.

Patrick isn’t just a triathlete, or a renewable energy leader, or a dad raising two adventurous boys. He’s a guy who once said yes to sailing a 26-foot boat with no refrigeration all the way to South America. A guy who climbed the Grand Teton without any prior climbing experience. But what really makes his story stick with you is what happened when all of that—his athletic identity, his mobility, his very sense of self—got upended in a moment.

In this episode, we talk about what it means to suffer well, how ego can drive growth, and why the most powerful moments in life often come through challenge. We talk about trust, adventure, the loneliness of injury, and the healing that comes when you’re surrounded by people who say, “I’ve got you.” If you’ve ever been forced to let go of something you thought defined you—this one’s for you.

⏱️ Timestamps

[1:12] – Patrick introduces his family and his lifelong pull toward movement and travel
[5:55] – A spontaneous dinner conversation leads to a year-long sailing adventure
[12:01] – Why shared suffering forges deeper connection than comfort ever could
[17:40] – Losing the ability to run, and finding new purpose beyond the podium
[30:17] – What happens when your body becomes the limiting factor—and you say yes anyway
[35:12] – Climbing Grand Teton without climbing experience: fear, faith, and the magic of the mountains
[47:40] – The unexpected rewards of pushing through what scares us
[56:00] – What it really means to “stay in shape for the next adventure”—and why it’s not just physical

🔗 Links & Resources

If you’ve ever had to redefine who you are, if you’ve ever stood at the edge of something scary and whispered “yes,” I hope this episode reminds you: you’re not alone.

And hey—if it did speak to you, don’t forget to share the love. Follow, rate, and leave a review to help On Adventure reach more listeners who need these stories just as much as we do.

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Episode 46: The Great Nearby – Chasing Wild in North Carolina with John Norwood


In this fun episode, Josh sits down with John Norwood, a commercial banker from Raleigh, North Carolina, whose second identity is that of a passionate adventurer. While John’s day job revolves around numbers and negotiations, his soul is stirred by trails, waterfalls, and sunfish sails. Rather than jetting off to exotic lands, John finds endless wonder in his own backyard—the mountains, lakes, and coastlines of North Carolina.

Together, they explore John’s lifelong connection with the outdoors, how he blends adventure with a full-time career, and how he’s cultivated a community of fellow explorers. From Christmas Day hikes to dry-suit sailing in winter winds, John shares stories that blend practical inspiration with a bit of wanderlust magic. 🌲🛶

⏱️ Timestamps

  • [00:00:00] Introduction to John Norwood and his adventurous alter ego

  • [00:03:00] Family traditions and the origin of the “dreaded Christmas hike”

  • [00:06:00] Sailing in dry suits and winter wind at Falls & Jordan Lake

  • [00:11:00] An unforgettable halibut fishing trip in Alaska

  • [00:16:00] Why John chooses to adventure local

  • [00:18:00] The magic of Grayson Highlands and wild ponies

  • [00:24:00] John’s roots in outdoor exploration

  • [00:33:00] The 11-year quest to complete 100 Classic NC Hikes

  • [00:37:00] Turning solo trips into a thriving hiking community

  • [00:41:00] The deep “why” behind adventuring: mental clarity, physical challenge, and spiritual renewal

  • [00:51:00] Upcoming trips: Cape Lookout Jeep expedition & AT alternatives post-Hurricane Helene

🔑 Key Takeaways

  • Adventure is everywhere – You don’t need a passport to find wonder.

  • Make space for solitude – Recharging happens when you unplug and reconnect with nature.

  • Community grows through shared challenge – John’s trips turned into a tribe.

  • Local treasures, lifetime stories – From Grayson Highlands to the Sycamore Trail sleep hack, there’s beauty in repetition.

“The trail gives me solitude, structure, and stories—and that’s what keeps me coming back.” – John Norwood

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Episode 45: What’s worthy of your finitude with Patrick Moody


I love these conversations, but this one was fun.  We hit on the depths of the human condition to drive each of us on to our own adventures.  So what happens when a dedicated trial attorney makes adventure a non-negotiable part of his life? In this episode, I sit down with Patrick Moody, a prosecutor for the state of Montana who refuses to let a demanding career keep him from chasing adventure. From trail running right out his back door to tackling high-altitude mountaineering, Patrick has found a way to integrate the wilderness into his daily routine.

We dive into his experiences traveling across five continents in a single year, climbing some of the world’s most stunning peaks, and even navigating a life-altering arthritis diagnosis that nearly took away his ability to walk. Patrick shares how he mentally and physically pushes through challenges, what drives him to keep pursuing difficult things, and why he believes that truly living means stepping into the unknown. This conversation is packed with insights on adventure, resilience, and making the most of the time we have.

Episode Highlights:

[1:30] – Patrick’s background as a Montana-based attorney and adventure-seeker
[3:15] – Why Helena, Montana is a paradise for outdoor lovers
[6:45] – The shocking arthritis diagnosis that nearly ended Patrick’s ability to move
[10:20] – How he rebuilt his body and got into trail running post-diagnosis
[15:45] – The lessons of adventure: losing a parent young and growing up without wealth
[22:10] – Learning to listen to his instincts on when to push forward and when to turn back
[31:05] – The scariest moment of his mountaineering career—trapped in a lightning storm
[35:55] – A year of adventure: how Patrick traveled to five continents in 2024
[44:30] – The importance of intentionality in adventure, career, and finances
[50:10] – Type 1, Type 2, and Type 3 fun—why suffering is part of the reward

Links & Resources:

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Episode 44: From high heels and fashion to hiking boots and fly fishing with Kimberly Brookshire


What would you do if failure was a real possibility? If suffering was inevitable, but you had the option to walk away? Would you still go for it? My guest today, Kimberly Brookshire, knows this challenge well. She’s a long-distance hiker, a women’s adventure guide, and a passionate fly fisher—always choosing the hard path, the uncertain path, because that’s where she finds the most growth.

In this episode, Kimberly shares her journey from fashion and city life to hiking thousands of miles on some of the toughest trails in the U.S. and beyond. She opens up about why she keeps pushing her limits, how she finds meaning in suffering, and the lessons she’s learned from guiding women through their own adventurous pursuits. Whether you’re an outdoor enthusiast or simply looking for inspiration to take a bold step in your own life, this conversation is packed with wisdom, humor, and a fresh perspective on what it means to live fully.

Episode Highlights:

[2:15] How a childhood filled with adventure led Kimberly to long-distance hiking
[6:40] The pivotal decision to hike the Mountain-to-Sea Trail—and why no one thought she’d finish
[15:20] Why guiding women’s adventure trips is about more than just the outdoors
[25:00] Handling adversity on the trail: lessons from near disaster
[37:45] The mental toughness strategies that keep Kimberly pushing forward
[45:10] Finding the balance between solo adventures and guiding others
[54:30] The Arizona Trail: what’s next on Kimberly’s adventure list

Links & Resources:

If you enjoyed this episode, be sure to subscribe, rate, and leave a review! It helps others find the show and keeps the adventure going.

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Episode 43: Beyond the Pavement with Frank Trotter


What do banking and backcountry exploration have in common? More than you’d think! In this episode of the On Adventure, I sit down with Frank Trotter—banking pioneer, entrepreneur, and avid adventurer. From his early days racing cars in Europe to co-founding EverBank and now launching Battle Bank, Frank shares how his career has been driven by innovation and a passion for pushing boundaries. But it’s not all business—Frank also dives into his love for outdoor exploration, from summiting 14ers in Colorado to backcountry treks in Argentina.

We talk about the lessons learned from extreme environments, the balance between risk and reward, and how his entrepreneurial spirit aligns with his drive for adventure. Plus, we dive into the incredible Excellent Adventures group and why surrounding yourself with the right people makes all the difference—whether in business or the wilderness.

Episode Highlights:

  • [2:00] Frank’s journey from hockey in St. Louis to racing cars in Europe
  • [6:30] The evolution of internet banking and why he’s launching Battle Bank
  • [10:45] The hidden ways big banks profit off their customers
  • [18:20] The Excellent Adventures hiking group and its impact on Frank’s outdoor pursuits
  • [24:15] Facing physical challenges—how a medical study changed his ability to keep exploring
  • [35:40] The connection between adventure, mindfulness, and perspective
  • [48:00] Knowing when to push forward and when to turn back—lessons from the mountains
  • [52:30] What’s next? Zion, GoPro Games, and upcoming adventures

Links & Resources:

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Make sure to subscribe, leave a review, and share with a fellow adventurer. And if you haven’t already, sign up for my newsletter, The Money Trail Guide, at www.ridgelinewealthadvisors.com to stay inspired on your financial and adventure journey!

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