Subscribe
Share
Share
Embed
Stories of adventure and lessons in wisdom from Justin Perkins and his network of founders, artists, leaders, athletes, and adventurers and Possibilists. This podcast explores the wonder and grit required to be a successful modern human, bringing big ideas into the world, with an emphasis on the Founder to CEO journey that is the ultimate modern rite of passage for creative humans. Host Justin Perkins is a serial entrepreneur, author, and founder coach, a former competitive athlete, musician and world adventurer. This podcast includes a mix of reflective rite-of-passage experiences, stories, and interviews with exceptional possibilists, intimate coaching sessions that led to breakthroughs, and a deep exploration of possibilism - a skill that anyone can develop. Possibilism is an upgrade to optimism - it is "someone who neither hopes without reason nor fears without reason, but sees progress because they are willing to look honestly at reality." And you will join the Possible List - a network of Possibilists - in creating your own list of what's possible.
A Long Walk With My Shadow: A Modern Rite of Passage Story
By Justin Perkins
In January of 2026, to celebrate my 50th year of life, I gifted myself a five-day wilderness trek along South Africa’s Wild Coast with about a dozen other men.
I thought I was just going for a beautiful hiking adventure with a bunch of amazing guys.
Little did I know it would obliterate the current version of myself and turn into a full-on rite of passage.
A blunt email subject line reading "Join the Pondo Wild Man" from Boyd Varty is what hooked me to do this trip. Boyd is the author of The Lion Tracker's Guide to Life, one of my favorite books.
Despite a demanding schedule, I immediately knew that I was going on this trip.
Several months later, as I purchased a waterproof backpack and a new pair of hiking shoes, I could feel myself squirming with a mix of excitement and anxiety.
Any hesitation passed as I finally boarded the overnight flight to Cape Town.
After one final night at the edge of civilization, a few hours getting to know the guys over a couple of meals, and a serene dip in the wild ocean waves at dusk, the trek finally launched the next morning.
We met our badass trek guide, Ash, and shoved off directly into the waves on kodiak rafts for an hour-long boat ride to the remote Pondo trailhead—a literal threshold crossing from civilization into a rare, wild, pristine place.
Just a few minutes into the ride, a pod of dolphins swam playfully alongside the boat, inviting us to dive in.
The captain cut the engine and gave his blessing to enter the water.
As I took a deep breath and submerged under the choppy ocean surface, I could hear the rapid sonar clicks of the dolphins, and I imagined they were playfully inviting us to let go and enjoy.
It was a precious moment, and the perfect ceremonial send-off from these liminal-threshold guides.
As we climbed back onto the boat, a spontaneous conversation with Boyd Varty unfolded about rites-of-passage and shadow work while we skimmed across the waves, straining to hear over the whoosh of the wind and ripping motor.
Shadow work is the practice of bringing attention to the hidden patterns, emotions, fears, and protective identities that unconsciously shape how we think, react, and relate to others.
Later that evening, after a dynamic day of hiking, waterfalls, and cliff jumping, basically on the movie set of the film, Avatar, Boyd gathered us in a circle.
He wasn't messing around. So much for chilling after an idyllic day. Instead, he issued a provocative invitation to dive right into the deep end of shadow work.
He provoked us to go around the circle and fill in the blank with this prompt: “The thing I don’t want you to know about me is…”
Despite being a trained coach, somewhat used to this sort of experience, for some reason, I hated this prompt.
This was not what I would have preferred to share in front of a group of accomplished guys, most of whom I’d just met.
But Boyd went first, and then we all sucked it up and jumped in.
One by one, as we each responded to the prompt, layers of armor dropped into the middle of the circle.
It's quite a rare thing to witness intimacy blossom from the vulnerable, real-time evaporation of shame - especially in a group of accomplished men.
Right below the surface tension lies a quiet invitation to deep connection. It's like stepping into the secret pocket behind a waterfall.
I was impressed at how universal it is that almost everyone is suffering, and nearly everyone in the group admitted to feeling a need to over-perform and be liked.
I had to wonder: if everyone feels insecure in groups, and often even more so at high levels of performance, then what would happen if we all let our guard down and stopped comparing?
Over the following days, the landscape unfurled into dreamscapes:
rugged cliffs, empty beaches, a hundred-foot-tall waterfall pouring into the ocean…
We soaked up the sun, the wind, the water, the land, and the rare space for long, intimate conversations on the trail.
An endless drone of rhythmic waves pounding the cliffs slowly rewilded our egos to the pace of our souls as we wandered across the land.
And yet, despite the caring men and the wild beauty around us, I could not seem to shake the feeling in my nervous system of being an outsider. I was acutely aware of a lingering, uncomfortable feeling of loneliness in my solar plexus.
It was a low, steady hum of energy that I could best describe as a feeling of insecurity that has lived in my nervous system since childhood.
When I'm in groups, the volume and intensity of this feeling increases.
It can feel like I'm standing behind a one-way mirror, unseen, excluded, and watching everyone else connect without me.
I even caught myself acting out this subconscious pattern by hiding behind my camera at times during this trip.
As a coach, I've witnessed time and again that embodied patterns in the nervous system clearly don’t dissolve just because you have talked about them or want them to go away.
Ignoring and suppressing deep emotions only tightens their grip. And I suppose that digging into the past and staying there doesn't really help, either.
As a human, I was tired of this endless, self-absorbed, lonely feeling that seemed to accompany me and bubble up unwelcome. And I could also see that thinking I should "just get over it" made it worse.
So, I tried a new experiment that I learned from a helpful book called "The Tools," by Phil Stutz.
I visualized a younger version of myself during a phase that really captured the feeling of being an outsider.
I conjured up the feeling of what it was like for me as a shy, lonely, thirteen-year-old boy with braces and awkward hair, not quite in step with the social dynamics at school.
This time, instead of pretending I’d outgrown this embodied fear, I stayed with the discomfort I felt in my nervous system at that age. I welcomed all of my awkward younger self to stay along for the ride, fully seen and included by me, the competent adult I am.
I let myself observe the familiar, stuck emotions, really felt the tension in my body, and noticed the impulses to seek attention or perform.
I noticed as my subconscious habitually tracked the micro-expressions in others and subtly gathered evidence to reinforce my old beliefs that I didn't belong.
I watched myself grow melancholy and allowed myself to withdraw when I needed to.
On day three of the trek, we came upon Bessie’s cave, a majestic cleft in the cliffs overlooking the seething ocean. Boyd invited us to do a "shedding" ceremony.
As we sat in a circle, one by one, we each offered up an outgrown story tainted with shame that was ripe for leaving behind in a cave like this.
Then, we claimed something true and empowering to carry forward in our lives in place of the shame.
The tender stories of adolescent boys slowly spilled out into the circle, gently absorbed by the cave. And what echoed back was the heroic alchemy of courageous men refusing to stay trapped as victims of the past.
I could feel an intense riptide of emotions pulling me under as I appreciated the suffering and courage behind each story.
The younger version of me would have fought back the tears of empathy and gratitude.
But after years of work to understand my internal process, I finally knew how to relax into this wave of energy and let the tears flow naturally without suppression as my turn approached.
The tears were appropriate, and I didn't hide them this time.
They accurately released the colliding clouds of emotion inside: empathy for others, grief for how my life might have been different without insecurity, and gratitude for the younger versions of myself and the others who had persisted and survived, despite the fear, to bring us to this exact, powerful moment.
With the intensity of fifteen souls quietly staring at me, I cherished the invitation to be raw and grabbed the rare space with my whole being. This surprised me even though intuitively I knew it was going to happen - as if it was an inevitable event planned for years.
Speaking slowly, I surrendered to where the energy in me wanted to go.
I asked the group to support me as I touched a feeling finally emerging beneath the grief and shame—a feeling I rarely access and could finally see seething below the patterned, stoic, nice guy personality that had served me well:
Raw, unfettered, powerful rage.
I stepped to the middle of the circle and invited the other men to huddle in close, surrounding me.
I closed my eyes and let myself be held, and then I let go.
A series of primal yells exploded out of me.
The sound that came up from deep inside of me was raw and feral.
It shredded my vocal cords.
I recall Boyd was right next to my face, matching my intensity with his eyes and voice, urging me deeper. This helped.
It felt so strange to have hands all over me, supporting my weight. I had a sense that I was a raging lightning rod for the whole group - not just for myself.
My mind was screaming to eject, but I stayed - there was no going back once I crossed the threshold.
So I bared down and squeezed every drop of anger from my body until I felt relaxed.
I remember cherishing a split second of deep peace and comfort in the silence, suspended like a marionette, held up by a powerful web of hands.
The circle held.
It was the only circle I'd found in my whole life that could hold the true, raw power of my intensity.
And for a man who cherishes words, it happened beyond the words.
The scream emptied something that decades of trying to fit in, explain, perform, or be perfect never could.
--—————————
But...
Relief didn’t last.
There was no tidy fairy tale ending.
There were no fireworks.
I wasn’t hoisted onto shoulders like I’d scored the winning touchdown as we transitioned out of the cave back onto the trail.
And it was time for the next man in the circle to have his turn.
As I sat with ears ringing, trying to listen to the others, an intense vulnerability hangover pulled me back under the waves.
Shame and loneliness whiplashed back into my system like an echo off the cave wall.
As the group dispersed, back onto the trail, what had felt inspired in the moment now just felt risky and regretful.
I know what it can feel like to witness something like this - it can feel awkward and uncomfortable to be with someone being awkward and uncomfortable.
So I feared the worst - that I had even further isolated myself.
But, as we continued along the trail, a couple of the men came up to thank me, privately.
It turned out that witnessing me access rage had given them permission to feel something they’d also been denying.
This external acknowledgment helped me settle - a bit.
A few minutes later, I joined the guys for a spontaneous dip under a massive waterfall tumbling straight into the ocean - one of the few places on earth where you can witness this phenomenon.
It felt good to hand the camera off to someone else and just relax and participate. The cold water made me feel alive as I watched from a dream state while the guys splashed, laughed, and played in the waves like children.
As we continued to wander, something was finally starting to emerge on the surface of this deep pattern for me:
I could see now that I had been the one bringing my own preemptive judgment that I didn't belong, before I even gave groups a chance to get to know me. And so it became a self-fulfilling system of isolation.
How could I belong or connect if no one knows me?
To be unknown is to be alone.
It turns out I was the one holding the invisible one-way mirror between myself and the connection I craved. It was an inside job all along.
On the final evening of day four, we were invited to spend a couple of hours alone, reflecting on the journey.
I found a shaded patch of sand overlooking the ocean, and a family of drifting goats showed up to graze on the sparse dune grasses near me.
The wild ocean hammered the beach while the wind kept playfully flapping the pages of my journal.
Despite the beautiful backdrop and a sense of gratitude for the privilege to be on this journey, a wave of sadness washed over me for a moment. I wondered if I’d missed it.
Had I missed the trip? Had I missed the chance, yet again, to connect and be known?
I imagine this is what it feels like towards the end of life.
Did I miss it?
The internal answer I heard in my head was a gentle and reassuring "no."
In fact, I had accomplished something quite intense and unexpected on this trip, not even counting the nearly 100 kilometers of walking across a remote part of Africa.
I realized how significant a change it was to hold back my usual jokes and performative stories, my go-to strategies to fit in, and allow something else - an uncomfortable experiment.
As I sat in this tension, reflecting, I realized a new, more authentic identity was emerging.
What was true was that I had actually connected deeply one-on-one with each of the guys. It just wasn't done in an unconscious, performative, or public way.
I felt awkward, perhaps, because I had gone beyond my limitations and tried something outside of my uncomfortably comfortable patterns.
And as I reflected further, I realized I had never actually been excluded by anyone on the trip.
That was an illusion and an old story I unconsciously preloaded and expected, long before the trip even started.
I had expected this dynamic for so long that it became an identity, maybe even a badge of honor, and a self-fulfilling prophecy I created in every group situation for the last few decades.
The experiment was totally worth it to finally expose this lie, and I didn't miss anything.
On the contrary, I started to see the profound freedom and future implications of this shift.
____________________________________________________________________
As I was about to return to camp, a surreal, unplanned moment unfolded.
The youngest man in the group appeared from behind the cliffs a few hundred meters down the beach.
Half my age, hair untamed in the wind, skin bronzed, he looked like a wild man.
He was carrying two long walking sticks, using them to balance as he waded across the rising tide in the waist-deep estuary.
As he approached, I stepped out of the shade and walked over to greet him on the beach.
With a trickster grin, he excitedly recounted his private adventure smashing sticks against rocks in an enchanted cove around the corner.
“You should go whack some sticks, too,” he said, not hesitating to hand me one of his sticks like a baton pass.
The invitation was exactly what the still-tender thirteen-year-old in me needed: play, noise, permission to be untamed.
So I walked to a pile of driftwood and started whacking sticks against rocks, inventing childish games, launching them into the surf.
The somatic action loosened something inside me. It brought me back from an internal monologue and into my body.
After losing myself in the play, I found myself making music, banging two short sticks together in a rapid rhythm, a primitive percussion that synced up with the ocean’s pulse.
All of a sudden, a primal melody rose from my throat—a guttural warrior’s sound, neither in English nor a language I could understand, but exactly right for the moment.
Singing by myself to the wind and waves felt like the final seal on this unexpected rite of passage.
Not because the feeling of the old outsider story and shadow had started to diminish, but because I had finally seen it, honored it, and invited it to play.
I could see the choice to honor the shadow as a valuable part of my initiation and development into a full-blown adult and leader, rather than hiding it as a shameful burden.
As the song naturally faded from my lips, I felt a deep gratitude for this place, and by extension, the men I shared this trail with for the past several days.
That evening, as transformational stories and laughter spilled out in our closing circle, it was a comforting reminder that most of us carry a personal version of the same imposter story.
It's a story of loneliness, a desire to be seen, and a hunger for connection that triggers self-referential thinking and self-consciousness.
And, I really saw from this experience that it's true - we have the power to connect with ourselves and generate a feeling of love and intimacy at any moment once we know how to see through the veil of perceived separation.
This poem spilled out in my journal on the redeye plane ride back to my home near Zurich, Switzerland, the next day:
I stay
Even though the body trembles
I stay
And as the mind accelerates, and the gut heaves,
I stay
And as all of the signals in my mind and body, seen and unseen, scream “run away”
I stay
I stay knowing there is an inner warrior guiding me back to center
And an earth supporting my weight
And a circle of souls
seen and unseen
holding me in a powerful web
I stay
even as I hear a primal roar erupting from the depths
My primal roar
echoing back in my ears from the walls of Bessie’s cave
I stay
And as I grieve out loud
held by a hundred powerful witnesses
whispering through me
echoing the beautiful rage of the ocean
pounding the cliffs below us
We stay
purging the shame
shredding our vocal cords
cleansing the humiliation caught in our voices
making gentle space for an ancient warrior's song to return
together, we stay
holding the unseen, frightened children
pulling the lightning into the rocks
and as a wild band of brothers
reunited
for a while longer
We stay.
I jumped right back into my first coaching calls with a couple of my clients a few hours after returning home from the adventure.
I was spent, a bit nervous, and was hyperaware of the drastic shift in context from Pondoland to Zoom as I fired up the first video call. Just twenty-four hours earlier, I was in one of the wildest places on the planet.
I was a bit surprised when the familiar imposter feeling bubbled up again.
But I took a breath, centered myself, and did my best to welcome the shadow back into the moment.
I didn't push it away. I knew this was important for integration.
As I looked into the faces of these clients, I noticed that I felt different. A little more raw - maybe even wild.
I settled into the conversation and listened to their challenges, noticing that I didn’t feel a strong impulse to fix them or to perform. Just to witness, be grateful, be in awe of them, and gently call and respond.
And, serendipitously, a few of the vulnerable insights from my experience on this inner journey came to my lips as just the thing to share with them.
What I'd seen in myself I could now see more easily going on in others, and I could more fearlessly hold a container for them, too, as a result of this initiation. My capacity had grown.
In the weeks that followed, this new baseline has held.
The veil has dropped, or maybe more accurately, it's still dropping or integrating.
It's a new possibility emerging, an ongoing experiment, where I'm more comfortable being uncomfortable - not knowing exactly who I am, but knowing that connection is always available, one breath, or one thought, or one conversation away, if I choose to be seen, if I choose to stay.