On Adventure Podcast with Josh Self

About On Adventure Podcast with Josh Self

A podcast of conversations with the Everyday Explorer. Why do we pursue adventure and what do we find when we push past our limits? Buckle up and enjoy the ride as we go On Adventure.

Publisher

Josh Self

Category

leisure · sports

Language

en

Explicit

No

First episode

28 Nov 2022

Latest episode

2 Oct 2026

Latest episodes

82 episodes in the feed.

1. 

   2 Oct 2026

   Episode 81: Why We Need the Wilderness - Identity, Purpose & Soul Rest with Todd Pinkston

   Most of us are constantly adding something to our lives - a better routine, another goal, a new piece of technology, one more strategy for getting everything under control. Todd Pinkston has built an entire organization around doing the opposite. As co-founder of Wayforward Adventures, Todd takes adults into the Southern Colorado backcountry for four- and five-day backpacking trips where the phones and watches stay behind, the distractions disappear, and participants aren't even told what time it is. The idea isn't to conquer the biggest mountain or push people to their physical limits. It's to remove enough noise that they can finally pay attention to what's happening beneath the surface. In this episode of On Adventure, Todd shares how a single question on a backpacking trip - "If money wasn't an issue and you could do anything to make a difference in the world, what would you do?" - helped launch Wayforward Adventures. Todd and Josh explore the fear underneath entrepreneurship, why high performers can struggle to surrender control, and the surprising reason people return from the trail physically exhausted yet deeply rested. They also dig into one of Todd's most important ideas: the difference between living for your identity and living from it. Along the way, they talk about leadership, faith, family, discomfort, purpose, and Todd's newest adventure - training for his first 100K ultramarathon. In This Episode Todd and Josh explore: Why Wayforward is built around subtraction, not addition The question that changed the trajectory of Todd's life Wrestling with "Do I have what it takes?" Entrepreneurship, anxiety, and learning to lead from a healthier place Why surrendering your phone, watch, and schedule can be harder than carrying a backpack The difference between physical rest and "soul rest" How the wilderness strips away the personas we maintain at home Why intentionally choosing discomfort can prepare us for everyday life The role of vulnerability and community in lasting change Living from your identity instead of for it Why Todd sees purpose as a daily practice Training for his first 100K ultramarathon Episode Chapters 00:00 — Meet Todd Pinkston Wayforward Adventures and the idea of using the backcountry to reset priorities. 02:00 — Football, identity & the outdoors Todd's early search for identity and the mentor who introduced him to backpacking. 04:00 — Ministry through subtraction Why removing distractions can sometimes accomplish more than adding another program. 05:00 — The question that changed everything "If money wasn't an issue, what would you do?" 07:00 — Do I have what it takes? Fear, entrepreneurship, and launching Wayforward Adventures. 11:00 — When grinding stops working COVID, leadership stress, and Todd's realization that deeper internal work was needed. 16:00 — Why the wilderness works Discomfort, authenticity, and what happens when the facade starts to disappear. 19:00 — The idea of "soul rest" Why people can finish a backpacking trip physically exhausted but deeply rested. 22:00 — Giving up control No phones. No watches. No schedule. No need to know what's next. 27:00 — Why adults need adventure How life experience changes what people bring into—and take away from—the wilderness. 30:00 — Managing risk in the mountains Altitude, acclimation, guide training, and knowing when to turn around. 33:00 — Why community matters Going below the surface and building relationships that continue after the trail. 35:00 — Choosing the hard thing How voluntary discomfort can reshape our relationship with adversity. 38:00 — Todd's first 100K Why he signed up for an ultramarathon despite the fear of failing. 40:00 — Running without distractions Long, slow miles as a space for solitude, prayer, and reflection. 43:00 — When suffering has a purpose Knowing the difference between productive challenge and simply pushing too far. 46:00 — Young guides leading accomplished adults What 21- and 22-year-old guides learn about trust, judgment, and leadership. 49:00 — It's all about perspective Why the exact same trail can feel completely different to two people. 50:00 — The cost of entrepreneurship Todd opens up about stress, marriage, family, and the harder years of building Wayforward. 55:00 — Living FROM your identity The difference between doing meaningful work and needing your work to prove who you are. 58:00 — Unstuck and Alive Recognizing and unlearning the stories that drive our internal dialogue. 1:00:00 — Purpose is a practice Why purpose isn't something we discover once—it's something we continually live. 1:03:00 — Where to find Todd & Wayforward Memorable Moments "We don't give ourselves what we actually need. We give ourselves the comfort that we think we want." Todd describes one of the biggest surprises of Wayforward: people return from several days of hiking and sleeping on the ground physically exhausted, yet they repeatedly say they feel rested. His explanation is that sometimes we need less physical rest and more soul rest—time when nobody needs anything from us and the phone isn't demanding our attention. Another question captures much of Todd's personal journey: "Am I living from my identity or am I living for my identity?" Living for identity means accomplishments continually have to prove something about us. Living from identity allows us to work hard without making the outcome responsible for telling us who we are. About Todd Pinkston Todd Pinkston is the co-founder of Wayforward Adventures, a Southern Colorado backpacking organization that takes adults into the backcountry for multi-day experiences centered on challenge, community, faith, and reflection. Todd's journey into the wilderness began in high school and continued through guiding backpacking trips in Southern Colorado. He launched Wayforward in 2014 after seeing firsthand how powerfully the backcountry experience could impact adults. What began with roughly 25 people on trail during the first summer has grown to hundreds of participants each year. Resources Mentioned Wayforward Adventures (https://www.wayforwardadventures.com/) — Multi-day guided backpacking experiences in Southern Colorado. Unstuck and Alive — Todd Pinkston and Steven Neuner's book exploring identity, purpose, and the stories that shape our lives. Unstuck and Alive Podcast — Conversations centered on many of the same themes. Also mentioned: Arthur Brooks, David Brooks' The Second Mountain, and the Bear Chase 100K. Connect with Todd Wayforward Adventures: wayforwardadventures.com Email: todd@wayforwardadventures.com The Takeaway Sometimes the next step isn't adding something. It's removing enough noise to hear what's already there. Todd's story is a reminder that adventure doesn't have to be about conquering the biggest mountain or proving how much discomfort we can endure. The wilderness can simply give us enough distance from everyday life to examine what is driving us, reconnect with who we are, and return home with a clearer sense of how we want to live. If you enjoyed this conversation, subscribe to On Adventure, share the episode with someone who could use a little less noise and a little more adventure, and join us for the next episode.

2. 

   18 Sept 2026

   Episode 80: Living Your Great Life Right Now with Monica 'Moss' Aguilar

   What happens when you build your life around the things that make you come alive - not someday, but right now? Monica Aguilar, known on trail as "Moss," is an artist, long-distance hiker, and everyday explorer who has intentionally built a flexible life around creativity and adventure. After graduating from UMass Amherst, she spent a season working in Alaska before thru-hiking the Appalachian Trail in 2018. Since then, she's continued exploring on foot and by bike, including the Pacific Crest Trail and more than 3,000 miles on the Continental Divide Trail. In this conversation, Monica and I talk about what keeps drawing her back to long trails - the community, the challenge, the highest highs and lowest lows, and the chance to experience a place slowly rather than simply passing through it. We also get into fear and risk, including difficult snow travel on the PCT and the decision to change course in Colorado's San Juans when challenge began moving beyond her comfort zone. But Monica's story is also about designing a life around what matters. She's built enough flexibility into her work, spending, and art business to disappear onto a trail for months at a time while still saving for what she calls "future Moss." That philosophy overlaps beautifully with something I talk about often: living your great life right now without ignoring the future. We also explore the connection between adventure and Monica's art. Through Chasing Trails Art, she creates murals, window paintings, and nature-inspired work influenced by the places she encounters along the way. Even there, she finds another version of doing hard things - the uncertainty and struggle of creating something that didn't exist before. Episode Highlights 00:00 — Meet Monica Aguilar: artist, thru-hiker, and unconventional career builder 08:30 — Working in Alaska and discovering space for creativity 14:00 — Taking on the Appalachian Trail as a relatively new backpacker 15:00 — Trail community, rainy days, and learning to embrace uncomfortable conditions 18:00 — Solo female hiking, trusting your instincts, and uncomfortable encounters 24:00 — Why Monica keeps choosing long-distance trails and hard things 25:30 — How "Moss" became her trail name—and why you should apparently pet the moss 29:00 — The PCT, CDT, and squeezing every last drop out of an adventure 33:00 — Snow travel, fear, and knowing the difference between growth and too much risk 39:00 — How Monica financially makes months-long adventures possible 42:00 — Saving for "future Moss" while still living for "now Moss" 44:00 — Turning nature and travel into Chasing Trails Art 50:00 — Why making art can sometimes feel harder than hiking thousands of miles 58:00 — Dreaming about a traveling mural tour and combining work with adventure 59:00 — Living your great life right now About Monica Aguilar Monica Aguilar is a Massachusetts-based artist, thru-hiker, and adventurer whose travels inspire much of her creative work. She has thru-hiked the Appalachian Trail and Pacific Crest Trail and completed more than 3,000 miles on the Continental Divide Trail. Through Chasing Trails Art, Monica creates murals, seasonal window paintings, and nature-inspired artwork drawn from the landscapes and experiences she encounters along the way. Connect with Monica Aguilar Chasing Trails Art (https://chasingtrailsart.com/) Instagram (https://www.instagram.com/chasingtrailsart/) Facebook (https://www.facebook.com/chasingtrailsart/) 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 along on Instagram and Facebook for clips and behind-the-scenes content, connect on Facebook at On Adventure Podcast with Josh Self, and find Josh on LinkedIn. If this episode resonated with you, leave a review and share it with someone who might need the reminder that you can prepare for the future while still living your great life right now.

3. 

   4 Sept 2026

   Episode 79: Why Altitude Humbles Even Experienced Climbers with Karl Frank

   _*]:min-w-0 gap-3 [&_>_*:last-child]:mb-0 print:block print:[&_>_:where(:not(:first-child))]:mt-3 font-claude-response" style= "box-sizing: border-box; margin: 0px; padding: 0px; outline-color: hsl(var(--accent-100)); display: grid; grid-template-columns: repeat(1, minmax(0px, 1fr)); gap: calc(var(--spacing) * 3); font-family: var(--font-claude-response); border: 0px solid var(--cds-border);"> What do you find out about yourself when the mountain sends you back down? In this episode of On Adventure Podcast, Josh talks with Karl Frank, a Colorado native, mountaineer, and President of A&I Wealth Management in Denver. Karl grew up hiking out the back door of his family's home at 7,000 feet, and he is now working his way through the Seven Summits. They discuss two very different trips up Kilimanjaro, a December summit of Aconcagua that most of the group did not finish, and a winter ascent of Mount Whitney where a single misstep by a teammate would have taken everyone off the wall. Underneath the stories is a running theme: the mistakes Karl remembers most are the ones that came from being sure of himself. In This Episode Growing up in the Colorado foothills and hiking alone as a kid Why he keeps looking for a personal limit he has not found yet Turning back at 16,000 feet on Kilimanjaro, and the trail that opened up because of it Altitude, arrogance, and the medical help he did not ask for Summiting Aconcagua in a bad weather year Frostbite, impaired judgment, and gear left in the pack Training on stairs and the Manitou Incline The Seven Summits plan, and why Denali is the hard one Faith, quiet, and the spiritual pull of high places Being genuinely afraid of heights and climbing anyway Episode Chapters 00:00 – The question behind every conversation Josh explains what he is really after: not the summit list, but the reward that keeps people going back. 01:00 – Growing up in the Colorado foothills Karl describes a childhood spent hiking alone at 7,000 feet, thirty years of marriage, and how easily you can lose yourself inside what you build. 02:30 – Two very different trips up Kilimanjaro A chest cold on a dry, dusty Lemosho Route turns into a turnaround at Barranco Wall, and a rare descent down the Umbwe Route. 05:00 – A Land Cruiser ambulance and a one room clinic The evacuation, the doctor who was unimpressed with his symptoms, and an antibiotic that is not sold for humans in the United States. 07:30 – When the detour becomes the trip Josh draws the parallel to planning. The contingency you never wrote down is sometimes the part you remember. 10:30 – Aconcagua in December Mendoza, a guide who has done the mountain sixty times, camps at 14,000 through 19,600 feet, and a summit on day twelve of a nineteen day window. 14:45 – A leveled camp and how you respond A climber walks into camp smiling after a night of 100 mile per hour winds, a collapsed tent, and altitude sickness. Karl's takeaway is about not judging what you can see. 16:00 – Turning around, frostbite, and judgment at altitude How Karl decides to push on or stop, the heavy gloves he carried and did not wear, and why you spot impairment in your partners long before yourself. 21:00 – Stairs, the Manitou Incline, and the Seven Summits His training approach, plus what is next: Carstensz Pyramid, then Denali, and why Denali is considered the hardest of the seven. 30:30 – Why he keeps going back Karl says he feels most alive when he is a little bit in danger, and explains the spiritual weight the mountains carry for him. 31:45 – The most dangerous moment: Mount Whitney in winter A traverse across concrete snow, a fifty meter runout, and a stretch where the outcome was entirely out of his hands. 38:30 – Calm, faith, and a droplet of water What he has learned about himself, and a Buddhist image about how briefly any of us are here. 43:45 – Facing a little fear, often Karl is afraid of heights. He explains how repeated small exposure lets him stay steady when the stakes are real. 46:30 – Skiing kids, football, and building A&I Raising three mogul skiers, a college football injury that changed his direction, three master's degrees, and how A&I Wealth Management got its name. Memorable Quotes "What's my personal limit? I haven't found it yet, so I keep pushing to find it." "You miss out on who you are if you just think about what you build." "It's how you respond to what the world lays out on you." "I feel most alive when I'm a little bit in danger." "We're here for just a little bit." Key Takeaways Turning around is not the same as failing. The Kilimanjaro attempt Karl did not finish sent him down a trail few climbers are permitted to use, and he counts it among the best hikes of his life. Arrogance is the real altitude risk. Two physicians in his group were carrying a full medical kit. He never asked, because he was the guy from the big mountains. Carrying the right gear is only half of it. He had his heaviest gloves in his pack on Aconcagua and skipped them to move fast. He lost the skin on the tips of all ten fingers and toes. Getting up is optional. Getting down is not. The summit is the halfway point, and most of the trouble starts after it. Face a little fear on purpose. Small, repeated exposure is what builds the calm you need when a situation turns serious. Nobody goes couch to Aconcagua. Capability gets layered in over years, and that is true well outside the mountains. Resources Mentioned A&I Wealth Management, assetsandincome.com (https://assetsandincome.com/) The Money Trail Guide, our free resource on planning for any adventure, minimizing trail waste along the way, and moving toward what matters most. Grab your copy at ridgelinewealthadvisors.com About Karl Frank Karl Frank, CFP®, MSF, MBA, MA, is the President of A&I Wealth Management, a second generation Colorado firm founded in 1986. He holds a Master of Arts in English from CU Boulder and a Master of Science in Finance and an MBA from the University of Denver. A Colorado native, former college football player, and lifelong skier, Karl has climbed many of Colorado's fourteeners along with Kilimanjaro and Aconcagua. He and his wife Stacy have three grown children. Keep Exploring Subscribe to On Adventure in your podcast app and on YouTube for more conversations with everyday explorers finding the edge of possible. Share this episode with someone who needs permission to turn around.

Who has been a guest on On Adventure Podcast with Josh Self

Names identified in recent episode analyses. Showing up to five guests.

• Holly Budge
• Jess Hanson
• Hudson Self
• Wells Jones

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

48

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

13 ratings

Spotify

5.0 / 5

4 ratings

Podcast Authority Score: 54 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

54

Social presence

0

YouTube

65

Engagement

71

Contact On Adventure Podcast with Josh Self

Guest appearances

Does not typically book guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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