Breakthrough
Adventure Retreats
for leaders
No Matter What
Immersive, high-impact expeditions that strip away comfort, build resilience, and forge real growth through challenge, connection and the wild.
These aren’t your typical leadership retreats. They’re not just another networking event or a vacation. These are once-in-a-lifetime journeys designed to expand who you are and how you lead.
Experience growth in real time
Whether you’re on a No Matter What Adventure or a Leadership Immersion, you’ll move through real challenge, deep reflection and meaningful connection. The kind that strips away pretense and brings you face to face with your own potential. Each experience is guided by seasoned facilitators and designed with care, combining physical movement, honest dialogue, and nature’s perspective to reset how you lead and live. Before and after the journey, structured integration ensures that what you discover out there becomes lasting change back here… in your work, your relationships, and your impact.
What You’ll Walk Away With
Real breakthroughs. Deep internal alignment. Tangible outcomes.
Unshakable Self-Trust & Clarity: Know who you are, where you’re going and how to act decisively, no matter the fear, doubt, or pressure.
Renewed Purpose & Inner Strength: Build the courage and confidence to face discomfort, make bold decisions and move forward even when it’s hard.
Embodied Resilience: Strengthen the connection between body, mind and spirit so you can stay grounded and lead with presence through any challenge.
Transformational Tools for Growth: Learn how to turn discomfort into growth long after the retreat ends, with practices you can use in your business, relationships and life.
Sustained Momentum & Meaning: Leave with the energy, alignment, community and the capacity to live a bigger, more meaningful life and reach your next level of performance, No Matter What.
Who are these
Adventures for?
These adventures are for leaders who feel the next chapter calling, and are ready to answer it.
You might be…
A founder or entrepreneur at a crossroads, personally or professionally
A C-suite or senior leader navigating change and seeking renewed purpose
A high-performing creative or innovator ready for deeper alignment
Someone who’s done the mindset work but wants transformation that lasts
A human drawn to real connection, meaning, and impact, not status or surface-level success
If that sounds like you, you’re in the right place.
Where growth becomes
a lived experience
Growth isn’t found in comfort, it’s forged through the unknown.
Every No Matter What Adventure blends:
Adventure: physical challenge that brings clarity and confidence
Culture: local wisdom and community woven into the journey
Integration: tools and reflection that translate insight into action
You’ll come home with the self-trust, focus, and presence to lead through anything, No Matter What.
Upcoming No Matter What Adventures & Immersions
Chile — The Space Between Worlds
Where silence reveals what’s real | August 1-8, 2026
A 3-month leadership journey culminating in an 8-day expedition through Chile’s Atacama Desert, one of the most awe-inspiring and silent places on Earth.
Morocco — Thresholds of Change
Cross the thresholds that separate who you’ve been from who you’re becoming | September 26 - October 4,2026
An 8-day journey from the Atlas Mountains to the Sahara Desert, designed to strip away distraction and reconnect you to what’s essential.
Mount Bierstadt, CO — Return to Simplicity.
Step out of the noise and back into presence | June 27, 2026
With its open meadows and steady climb, Bierstadt invites you to slow down, breathe, and remember what matters most. In a world racing forward, this climb is about reconnection, to yourself, to others, and to the ground beneath your feet.
Mount Quandary — Discernment in uncertainty
Leading when clarity disappears | July 17, 2026
The trail’s changing weather and steep switchbacks demand presence over prediction. Each step becomes a lesson in trusting intuition and staying grounded when direction blurs. This climb isn’t about mastering uncertainty, but moving with it.
Mount Blue Sky, CO — Lead with Awareness. Rise with Integrity.
A call to lead through care and responsibility | August 20, 2026
Renamed to honor the Arapaho “Blue Sky People” and the Cheyenne “Blue Sky Ceremony,” it reminds us that leadership is about presence, not power. Each step invites reflection on how we use influence to uplift others and the world around us.
Grays Peak, CO — Strength in Tension.
A metaphor for integration | September 19, 2026
Twin to Torreys, it represents the meeting of opposites—drive and stillness, self and team, inner and outer worlds. The rugged saddle between summits challenges you to find balance amid duality, turning tension into connection. Grays closes the series with a simple truth: leadership isn’t about conquering mountains, it’s about crossing them together.
Thailand — Leadership and Soul
An invite-only women’s retreat | June 12-18, 2026
Begin in the stillness of Khao Sok—limestone cliffs, emerald waters, and time slowing to breath. Kayak misty lakes, explore hidden caves, and connect with elephants in their sanctuary. Then move east to the Gulf of Thailand: yoga by the sea, coral reefs, and creative expression on Koh Phangan. A journey of reflection, connection, and renewal—where leadership grows grounded, alive, and open to possibility.
-
This proved that the ‘impossible’ is often just untested potential—pushing me mentally, physically, and spiritually beyond what I once thought I could do.
JASON
-
“This retreat changed how I show up in my life.”
BIRAME
-
I came for growth. I left with a deeper understanding of myself, my purpose, and a community I’ll carry for life.
ANDREW
Real Growth.
Lasting Impact.
Every expedition reshapes what’s possible. Hear from those who said yes, and never saw life the same again.
From the Andes to the Sahara, every No Matter What Adventure transforms challenge into clarity. Leaders return home grounded, reconnected, and ready to lead from a deeper place of truth.
Transformation
In action
These experiences aren’t escapes, they’re high-return growth systems...
Designed for high-level leaders, each No Matter What Adventure follows a proven process that bridges inner change with measurable results.
From identity to innovation, discomfort to trust, and insight to sustained growth, each phase compounds into lasting transformation.
Ready to Explore a Breakthrough ExperiencE?
Complete the short application form below and we’ll be in touch to help guide your next step, No Matter What.
If you’re interested in a 1:1 Personal Breakthrough Lab session with Sterling or bringing No Matter What to your company, please contact us for more details or visit…