Five years ago, Ryan Conklin stood at the intersection of devastating loss and profound possibility. His dream job eliminated. His identity shattered. Everything he'd built carefully constructed around his career in the spirits industry—gone in a single day.

But instead of numbing the pain, Ryan made a vow that would transform his life: "Stay awake for this." That same day he quit drinking, not because he labeled himself with any particular identity, but because he chose presence over escape. What followed wasn't just recovery—it was a complete remaking of how he related to himself, his purpose, and the wilderness both outside and within.

Ryan's journey from spirits industry professional to vision quest guide reveals something profound about the nature of transformation: sometimes our greatest breakdowns become our most essential preparation. Through his Substack "Maps of the Inner Wild," he explores what becomes possible when we stop running from our unraveling and start listening to the quieter voice that emerges from stillness.

Show Notes

[00:00] The Mirror Moment - When Identity Disappears

Ryan describes the moment he couldn't recognize himself after losing his job and relationship
The disorientation of asking "who am I?" outside of professional identity
Why some breakdowns are actually breakings-open rather than breakings-down
The choice between staying in victimhood or empowering transformation

[05:00] From Hospitality to Spirits - A Career Built on Connection

31 years studying "how what we do makes people feel" through hospitality
The spirits industry job that required visiting 8 bars per day with a $4,000 monthly entertainment budget
How professional success can become a sophisticated form of numbing
The difference between creating experiences for others vs. staying present to your own experience

[10:00] The Leadership Program That Changed Everything

"You can't lead others until you can lead yourself" - the teaching that sparked transformation
Moving from preparation for promotion to accepting demotion with dignity
How shadow work and facing discomfort became the foundation for real leadership
The retreat experience that whispered "walk with me" and led to vision quest training

[15:00] Shifting from Monologue to Dialogue

The revolutionary practice of turning self-criticism into self-curiosity
Practical example: How to handle distraction (like scrolling social media) with compassion
"Curiosity is literally a synonym for love" - showing up for yourself with genuine interest
Moving from "you're terrible at this" to "what's going on? what do you need?"

[23:00] Creativity as Survival and Remaking

Ryan's background in professional snowboard photography before spirits
How 5 years of survival mode (parents' health crises, career loss) shut down creative expression
The vow to play: "engaging with something without a need for outcome"
Learning flute, fly fishing, and bow hunting as acts of creative rebellion

[33:00] Vision Quest - Holding Space in the Wilderness

The 9-day process: preparation, 4 days/nights alone on the land with no food or shelter
Sitting inside a question, drawing a spiritual circle, being held by guides
The challenge of returning to society after deep wilderness attunement
How guiding others through transformation has become Ryan's creative expression

[38:00] The Wildest Place We'll Ever Know

"The wildest place we'll ever know is inside of ourselves"
Connection defined as feeling heard, seen, met, felt, honored, and celebrated
The correlation between depth of self-connection and ability to connect with others
Wilderness as the art of noticing - accessible in backyards and bus stops, not just remote forests

[43:00] Making Decisions from a New Place

Shifting from "Am I safe? Do I fit in? Seeking the blessing?" to "I am safe. I belong. Embodying the blessing."
How trauma creates survival-based decision-making patterns
The ontological approach: studying who we're being in everything we're doing
Creating from the future rather than reacting from the past

Key Quotes

"The wildest place we'll ever know is inside of ourselves." - Ryan Conklin

"Curiosity is literally a synonym for love, and when we can show up from a place of love towards ourselves, it makes so much more possible." - Ryan Conklin

"My invitation, my work, is shifting it from a monologue to a dialogue. Shifting these voices, these thoughts from monologues to dialogues... taking something that is internal self-criticism or judgment and shifting it into an allyship." - Ryan Conklin

"Vitality lives on the other side of grief. And grief is not something to be done or completed or moved through, but actually something to be in deep relationship with." - Ryan Conklin

"The way I define play is engaging with something without a need for outcome. Just doing something just to do it." - Ryan Conklin

Resources Mentioned

Maps of the Inner Wild - Ryan's Substack exploring transformation and wilderness connection
The Bridger Coaching - Ryan's coaching practice
Man Uncivilized/Uncivilized Nation - The men's organization where Ryan leads chapters
Vision Quest/The Initiation - 9-day wilderness transformation experience
Rumi's poetry - "Beyond ideas of right doing and wrong doing, there's a field. I'll meet you there"
Tom Brown's Tracker School - Wilderness awareness and primitive skills
John Young's bird language teachings - Connecting with nature through observation
Sit spot practice - Regular time in one outdoor location to deepen awareness

Where to Find Ryan

Website: TheBridgerCoaching.com
Substack:
LinkedIn: Connect for thoughtful conversations about transformation
Availability: Open to connecting with readers in Denver or via phone calls

The Wisdom of Undoing

Ryan's story reveals something essential about the creative life: sometimes our greatest art is the remaking of ourselves. His journey from spirits industry to vision quest guide shows how transformation becomes possible when we stay present with our breaking points instead of numbing them.

If Ryan's approach to wilderness connection and men's work resonates with you, I encourage you to explore The Bridger Coaching and his community work with Man Uncivilized.

For creatives specifically seeking to align their artistic practice with sobriety and authentic purpose, The Sober Creative offers a complementary path focused on the intersection of creativity, clarity, and sustainable business practices.

Thank You

A heartfelt thank you to , , and everyone who joined us live for this conversation, and to Ryan Conklin for his extraordinary wisdom and vulnerability. Your willingness to share your journey of staying awake through life's breaking points offers hope to anyone navigating their own wilderness.

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Episode 009 - When Everything Falls Apart…