Climb Higher. Grow Deeper. Lead No Matter What:
Mount Quandary
No Matter What 1-Day Growth & Leadership Immersion: Quandary Peak (14,265 ft)
Discernment in the Face of Uncertainty
This experience brings leaders face-to-face with the paradox of uncertainty. Quandary Peak—its name itself a symbol of confusion and choice—reveals how clarity often emerges from chaos.
Once part of the Sky Path traveled by the Ute and Arapaho, this landscape was considered a place where the veil between worlds thinned, where silence became teacher. Here, altitude meets ambiguity—and both become mirrors for leadership in uncertain times.
The question isn’t whether you can find the path. It’s whether you can stay present when the path disappears.
“The unknown isn’t what stands in the way—it’s the path itself. Every step into uncertainty is a step into leadership.” - Sterling
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Discernment — Cultivate clarity amid uncertainty
Quandary teaches that clarity isn’t found by forcing answers—it emerges by staying with the questions. As you climb, each moment of doubt becomes a chance to listen more deeply: to your breath, your instincts, and what’s truly calling you forward. You’ll learn to navigate complexity not by eliminating it, but by finding calm within it.
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Presence — Strengthen focus when direction blurs
When the path disappears into fog or rock, the only next step is the one in front of you. This mountain becomes a live exercise in attention—how to stay anchored when things feel unclear or shifting. Presence becomes your compass, guiding you through uncertainty with grounded awareness.
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Courage — Lead without needing control
At altitude, leadership transforms. Control gives way to courage, and certainty gives way to trust. Here you’ll experience what it means to move forward without a guaranteed outcome—to lead from conviction rather than confirmation. This is where authentic leadership is forged.
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Trust — Build inner steadiness in external ambiguity
Quandary asks for a quiet kind of trust: not blind optimism, but embodied confidence. It’s learning to rely on what doesn’t waver—your breath, your integrity, your presence—when everything else feels unpredictable. That’s the trust that separates reactive leaders from resilient ones.
Growth doesn’t happen when things are easy.
It happens when you step into the unknown — and stay long enough to see what emerges.
In business, in life, and in leadership, that’s the real edge.
This adventure gives you the tools and the trust to navigate it — No Matter What.
Container details
TRAVEL BRIEF
Overview
Container at a glance
Total Duration: 1 day (mountain climb) + 2 online sessions
Format: Live pre- and post-adventure Zoom calls, plus 1 full-day mountain immersion
PRE-ADVENTURE (Zoom 1) | 60 min
Intention-setting, mindset preparation, and physical readiness overview
Framing the climb through the No Matter What ethos: commitment, presence, and trust
Orientation on logistics, gear, and group coordination
DAY OF ADVENTURE | Full Day (Approx. 10–12 hours roundtrip)
Early Morning Start (3:30–4:30 AM): Trailhead departure under headlamps
Ascent: Guided climb with reflection prompts and group check-ins
Summit Experience: Ritual circle at the peak, honoring what’s been overcome and what’s being called forward
Descent: Embodied integration, translating lessons into leadership application
Evening Return: Community debrief over shared meal or celebration
POST-ADVENTURE (Zoom 2) | 60 min
Guided reflection and actionable integration
Accountability framework for sustaining growth
Shared commitments: how each participant will carry the No Matter What mindset forward
“This journey gave me clarity for the next chapter of my life and the courage to live it with authenticity and joy.”
“This transformed how I lead, how I show up, and how I see what’s possible”
“This wasn’t a typical retreat. It was a space that brought out connection, reflection, and growth.”
Who is it for?
For executives, entrepreneurs, and changemakers ready to grow beyond achievement.
For founders, team leaders, and high-potential professionals navigating change.
For creators, coaches, and culture-builders committed to growth that serves others.
Inside
your trip.
Duration:
1 day (mountain climb) + 2 online integration sessions
Dates:
COMING SOON
Location:
Colorado Front Range — (Mount Quandary)
Investment:
$2,400 USD per participant
(50% deposit required to confirm spot)
Group Size:
Limited Group Size
(limited intentionally for depth, safety, and connection)
Included:
1 Pre-Adventure Zoom preparation session
1 Full-day guided 14er climb with professional guide and No Matter What facilitation
1 Post-Adventure Zoom integration session
Reflection workbook + growth framework
Group communication & logistics support
Optional post-climb meal and celebration
Not Included:
Travel, transport, meals or lodging
Meet Your Guides
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Sterling Hawkins is an author, investor, entrepreneur, and keynote speaker who is globally
recognized as a thought leader in personal and organizational growth. Founder of the No Matter What Movement, he shows people how to achieve the performance, results and fulfillment they want regardless of obstacles.
Sterling developed his methodology to learn from the painful collapse of his multibillion dollar startup involvement. He's since combined his business background, research, study and practice to come back and launch, invest in and grow more than 100 companies. He's taken that experience to work with C-level teams and leaders and speak on stages around the world. He's been featured in magazines like Forbes, Fast Company, The New York Times and Inc.
He believes that there is no growth without discomfort – and it requires courage, commitment, community and the cultivation of trust to move through the uncomfortable and uncertain and into breakthrough results. To inspire people to unlock their own inherent potential, he shares key practices that help us push beyond our perceived limits to make a difference for our companies, communities and families. When he's not at home in Colorado, he may be out skydiving, swimming with sharks or adventuring with the No Matter What Movement.
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Haviland Hawkins is an entrepreneur, strategist, and keynote collaborator who co-leads the No Matter What Movement alongside her brother, Sterling. Together, they design and lead immersive leadership retreats and adventures around the world (from the mountains of Peru to cultural immersions in Africa) each crafted to challenge limits, spark transformation, and inspire breakthrough results.
With a background in marketing strategy, operations, and transformational leadership, Haviland has worked with Fortune 500 companies, entrepreneurs, and global organizations to drive both personal and organizational growth. Her expertise lies in translating bold ideas into actionable outcomes, ensuring that the No Matter What methodology extends beyond the keynote stage into lasting change for individuals, teams and companies.
She believes growth requires courage, commitment, and community. Through her work, she creates spaces where people can confront discomfort, unlock their potential, and discover what they’re truly capable of. Whether uniting executives across cultural barriers, supporting leaders in breaking free of limiting beliefs, or guiding participants step by step on the Inca Trail, Haviland blends clarity, compassion and challenge to deliver breakthrough results.
When she’s not home in Colorado, you’ll find her alongside Sterling, leading No Matter What adventures and retreats or exploring new frontiers that continue to push her own edges.
Ready to lead into the unknown?
This 1 day immersion is intentionally limited. Every application is reviewed to ensure the group is the right fit for each other and the experience. Please answer the questions honestly and from the heart…there are no “right” answers.