Why a CEO Wept in the Wilderness
and Why It Changed Everything
Picture a CEO. Used to the 100-hour weeks, the performance metrics, and the constant management of perception. He is at the summit of the corporate ladder and silently, profoundly, miserable.
On day three of a camel-supported trek through remote northern Kenya, that CEO finally broke. He wasn’t overcome by the heat or the miles. He was overwhelmed by relief.
For the first time in years, the armor came off. There were no urgent pings, no quarterly targets, and no one demanding a performance. Just the vast, silent wilderness, the grounding presence of Samburu elders, and a temporary tribe who saw him for the man he was, not the title he held.
In that desert silence, the deep, collective human ache for true belonging cracked the surface. Not belonging to a network or a balance sheet, but belonging to the land and to each other.
This story comes straight from my conversation with Oli Raison and Boris Maguire, founders of Safarini Leadership—a journey that is shattering everything I thought I knew about what makes a great leader.
When Leadership Means Letting Go
Safarini means “on a journey” in Swahili. And that is exactly what they facilitate: 10-day, device-free journeys into the wilds of northern Kenya. No hotel seminars, no PowerPoint presentations, just a six-day trek through deserts and mountains with the only unavoidable escape being yourself.
Oli and Boris didn’t discuss efficiency models or growth hacking with me. They talked about “naba wisho”: the essential Samburu philosophy, meaning, “we are because they are.” Pure, radical interdependence.
This stands in contrast to the Western corporate ideal: solo grit, quick money, and extreme independence.
The Samburu measure success not by speed, but by the journey. Elders, who spend 15 years serving the community as warriors before assuming the collective decisions of eldership, possess resilience forged in shared roots, not isolation. They have no word for anxiety or depression because they live knowing their neighbor shares without resentment, across generations.
They told me a breathtaking story: A man loses his camels to drought. Years later, he asks total strangers to return camels originally gifted by his great-grandfather. They do. Instantly.
In our world, this is a beautiful impossibility. In the wild, it is the quiet logic of survival and serene joy.
What the Wild Reveals (That Data Never Will)
The traditional leadership playbook is fast, fragmented, and inbox-haunted. Our brains are buzzing on high-frequency noise, leaving no space for genuine insight.
Safarini reverses the equation.
Walking shoulder-to-shoulder with elders, a scientifically proven technique for deeper conversation, executives unpack indigenous truths: resilience is collective support, not solo grit; harmony is prioritized over dissent; decisions honor both ancestors and descendants.
When executives arrive, they are armored, quietly lonely, and focused on control. They leave transformed: lighter, more present, and equipped to build real belonging back home.
One executive, used to wearing a shield of negativity in her male-dominated industry, was changed by a simple observation from an elder: “Why look down? Beauty surrounds you.” A life-altering shift began with those few words. She now leads with her gaze up, radiating positive energy.
This is the power of ancient wisdom meeting modern burnout.
The Question Burning in Me Now
In our hyper-connected, deeply isolated world, we are trading relational wealth for material accumulation. We are prioritizing speed over depth.
What are you doing each day to reconnect truly?
Not just to nature, powerful as it is, but to the people, to the purpose beyond next quarter’s numbers, and to the truth that real strength grows from shared roots?
The wilderness doesn’t rush you. It waits until you slow down enough for it to reveal the truth. And this is the essential truth revealed by the Samburu: Belonging is not a perk you build in a boardroom.
The boardroom builds a hierarchy. The wild remembers a tribe.
Your Turn.
Where in your leadership or life do you feel that ache for deeper connection right now, and what’s one small step you could take toward it?
Hit reply. I read every one.
More Resources
→ Listen to the full episode on Passion Struck
P.S. Download your free companion workbook here. It includes:
Prompts for reflecting on your true leadership values.
Exercises for reconnection in a disconnected world.
A 3-question “Belonging” audit.
If this resonated deeply, share it with a leader grinding metrics but craving real meaning.
I feel this aching for my life’s project. I’m so thankful and blessed for my wife and my amazing family, and I wake up every day, motivated to love them. But in the hours after everyone else has gone to bed, I sit awake trying to create something of my own that I can pour all of my heart into.
I started my Substack to find people who are doing what I want to do, such as yourself, and I’m hoping that diving into the wilderness of the unknown will reveal my North Star.