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

 

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Hosted by Josh Self, financial advisor and everyday explorer.

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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

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Episode 32: Epic Adventures and Life Lessons with Skip Schweiss


In this episode of the On Adventure podcast, I sit down with Skip Schweiss, a seasoned executive in the financial services industry and a passionate adventurer. Known for his years of leadership at TD Ameritrade, Skip has seamlessly woven his professional life with a personal quest to push physical and mental boundaries in the great outdoors. We dive into Skip’s career journey, from his work in advisor advocacy to how he’s now dedicating more time to his love of the wilderness.

But Skip isn’t just about hiking the occasional trail—he organizes an annual group hike called “Excellent Adventures,” attracting dozens of people to tackle challenging hikes across some of the most beautiful landscapes in the U.S. From the majestic peaks of Colorado’s 14ers to this year’s adventure in Telluride, Skip shares his motivation for doing hard things, the camaraderie that comes from shared suffering, and why he believes that testing our limits makes us better.

Whether you’re a seasoned adventurer or someone looking for inspiration to push past your comfort zone, Skip’s stories will encourage you to set bigger goals, embrace the challenge, and find joy in the journey.

Episode Highlights:

[2:42] – Skip’s journey in the financial industry, his role at TD Ameritrade, and how his love for adventure began.

[7:00] – How the Rockies ignited Skip’s passion for hiking, leading him to complete all 54 of Colorado’s 14ers.

[12:15] – The origin of Skip’s “Excellent Adventures” group hikes, which have now grown to include 70 people, and the importance of camaraderie in adventure.

[29:00] – Handling adversity on the trail: The lessons Skip has learned about staying calm when things go wrong, and how to apply that mindset to life.

[40:30] – A recap of the most recent “Excellent Adventure” in Telluride, where Skip led a group on a brutal 26-mile hike with 8,000 feet of elevation gain.

[52:00] – What’s next for Skip and the group? A sneak peek into next year’s adventure to Zion National Park and some of the epic hikes planned.

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