Part II: The Cowboy Stage: Risk, Wounds, and the Wilderness That Still Calls My Name
A masculine initiation journal from Park City, Utah
“And [the boy] grew in wisdom and stature, and in favor with God and man.” –Luke 2:52
In the high mountain air of Park City, Utah, I’ve been walking a road I didn’t fully understand until recently…a road mapped not by business plans or backcountry trail markers, but by the soul’s need to be fathered. This is the Cowboy stage of masculine initiation, and it’s not about horses and hats. It’s about risk, sweat, and the question that echoes in every man’s heart:
“Do I have what it takes?”
This article is one chapter in a broader content series I’m writing around the stages of masculine initiation, guided by John Eldredge’s Fathered by God, which is a subsequent stage after the Wild at Heart experience. My first article, Embracing the Ancient Paths: A Wilderness Journey of Masculine Initiation, describes my experience of the first phase of the journey, Boyhood. Read it first, if you haven’t yet.
Now to this article…
After years of building companies, surviving loss, and chasing validation, I’ve come to realize something profound: I’ve done a lot of things, but I never truly completed my initiation.
And now, in midlife, I’m letting God father me through it.
What Is the Cowboy Stage?
According to Eldredge, the Cowboy (or Ranger) stage usually begins around age 12 and can carry into a man’s mid-20s. It’s the time when a boy longs for risk and adventure, when his soul starts craving answers to deeper questions:
- Can I handle real danger?
- What am I made of?
- Will I rise when tested?
It’s a season defined by doing. By hands-on, often physical, experience. Boys in this stage learn through getting hurt, getting back up, and trying again. They need mentors , not lectures. They need to face hardship, not be shielded from it.
But here’s the catch: many of us missed it.
Some of us never got the adventures.
Some of us had no one to take us there.
Some of us were thrown into overwhelming work or risk too early–and failed, without any guide to help us interpret the failure.
And all of it left a wound.
My Cowboy Phase: The First Round
I didn’t miss the Cowboy phase.
I survived it.
My first “adventures” were raw and fast. At 16, I was running my own small business. Not the lemonade stand kind the kind where real money was made, lost, and fought over. I dove headfirst into life: entrepreneurship, fraternity life, risk-taking, and physical challenges. I wasn’t the kid playing pretend, I was in it.
I love my Dad, and he is my hero but most of the journey I didn’t have a guide. I was praised for being smart. For being bold. I learned how to win. But I didn’t learn how to fail well. I didn’t learn how to grieve. I didn’t know how to hear the words every young man needs: “You have what it takes.”
I remember trying to prove myself in ways that, now, I can see were more about fear than strength. There was no healthy initiation — just performance. Just hunger. Just hustle.
What I Sucked At
Looking back, I was a terrible listener to my own limits.
I “sucked at” knowing when to rest.
I sucked at asking for help.
I sucked at failing without letting it define me.
Even though I was outwardly succeeding–founding companies, making money, traveling the world–I was inwardly building a life that couldn’t hold up under pressure.
And eventually, it collapsed.
The Second Round: Cowboy, Revisited
Fast forward to now.
I’m in my 40s. I’ve built and exited companies. I’ve lost relationships. I’ve faced heartbreak, doubt, and the deep ache of unhealed masculine wounds. And I’ve come to believe something:
God is bringing me back to the Cowboy stage — so we can finish what was left undone.
So I came here–to the mountains.
To Park City.
To hike.
To write.
To listen.
To be fathered by God.
This isn’t nostalgia. It’s not about “going back.”
It’s about healing through experience.
When I hike a trail alone at dusk and face my fear of mountain lions or hiking in the dark–that’s the Cowboy phase.
When I carry the emotional weight of my past but still lace up my boots and move forward–that’s the Cowboy phase.
When I confront the silence, away from performance and productivity–that’s Cowboy, too.
“Do I Have What It Takes?” (Still Echoing)
That same question from my teenage years hasn’t gone away.
It’s just changed shape.
Back then, I asked it by launching businesses and chasing adrenaline.
Now, I ask it as I stare down my deepest fears:
- Am I worthy of real intimacy?
- Can I build something that lasts–this time?
- Will God really show up for me?
And maybe the most haunting question of all: Is this just another cycle of almost-getting-there, or will something actually change?
There’s a weariness that comes from living in a pattern of peaks and crashes. I’ve been a rocket-ship, and I’ve crashed into the ocean. I’ve been the golden child–and the prodigal. I’ve been celebrated: and very, very alone.
I’m tired of cycling through roles.Now, I want to become a man who walks in a larger story.
The Risk of Hope
It’s risky to hope again.
To believe that God might ask something big of me.
To think that maybe I wasn’t disqualified by my failures, my losses, or my wounds.
That hope doesn’t come easily.
There’s a voice that says:
“God wouldn’t ask that much of you.”
“You’ve already had your chance.”
“Just play it safe. Build something small. Be comfortable.”
But I don’t want comfort anymore.
I want courage.
I want clarity.
I want the kind of life that requires a King’s heart, not just a clever brain.
Remembering David
Eldredge reminds us that David was a Cowboy.
Before he was a king, he was a shepherd.
Before he faced Goliath, he fought off lions and bears.
Those trials weren’t glamorous–but they meant something. They gave David a quiet confidence–not arrogance– that God was with him.
I want that kind of confidence.
Not puffed-up certainty.
Not performative masculinity.
Just presence.
Presence is the proof.
I’m Still in the Middle
Let me be clear: this article isn’t a triumphant conclusion.
It’s a field note.
I’m still on the trail.
I have been divorced 3 times.
I don’t have the million-dollars in my bank account.
I don’t have the “all is well” ribbon tied around my story.
What I do have is a willingness to be led.
To be tested.
To be fathered by God, even now.
And maybe that’s all the Cowboy stage is about.
To the Men Still Wondering
If you’re a man reading this and you feel like you missed something on the way to adulthood– you probably did.
But it’s not too late.
If you never had a guide, let this series be one.
If you’re tired of chasing wins and want a life with roots, not just wings — you’re not alone.
If you’re ready to let God take you into risk, adventure, hard work, and healing–this is your sign.
This series continues.
Next up, I’ll be writing about the remaining phases: Warrior, Lover, King, and Sage. I will be attending a surviaval school retreat, and the Becoming a King retreat. Each of these post will be part story, part reflection, and part invitation to any many who wants to walk the ancient paths again.
Until then, keep walking.
Even if the only way forward is through hell and discomfort.
