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 — 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: [email protected]

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.