The Pikes Peak Leadership Immersion
No Matter What 1-Day Growth & Leadership Immersion: Pikes Peak
1 Day Immersion
Pikes Peak, CO
August 20, 2026
Reverence and Responsibility
Pikes Peak isn’t just a landmark on the Colorado horizon; it’s a 14,115-foot reminder of what’s possible when we get above the noise. But here’s the thing: we aren't climbing to "conquer" a mountain. We’re climbing to find some much-needed clarity.
When you get high enough, the daily fires and endless emails start to look pretty small. In that space, leadership stops being about "control" and starts being about stewardship, taking care of your vision, your team, and yourself. It’s a day to slow down, breathe deep, and trade your blind ambition for real awareness.
“The unknown isn’t what stands in the way—it’s the path itself. Every step into uncertainty is a step into leadership.” - Sterling
-
Lead in a way that matches what you stand for
Pikes Peak is a chance to look at how your actions line up with your values. Integrity is not just about what you believe. It is about how you lead when things get hard, unclear, or uncomfortable.
-
Understand your impact
This mountain carries history, change, and meaning. It invites you to lead with more awareness of how your choices affect other people, the systems around you, and what comes next.
-
Lead with care, not ego
The climb is a reminder that leadership is not about proving yourself. It is about showing up with respect, staying grounded, and creating space for others to grow.
-
Build real community through shared challenge
Doing something hard together creates a different kind of bond. Through the climb, reflection, and shared experience, connection becomes more honest, grounded, and real.
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:
August 20, 2026* Date subject to change with weather
Location:
Colorado Front Range — (Pikes Peak)
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
-
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.
-
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?
Includes pre/post sessions, guided climb, and reflection workbook. Note: This is an intentionally small group. Every application is reviewed to ensure a cohesive, high-impact environment.
The Inner Journey
of No Matter What Leadership
Our No Matter What Process
Where personal transformation becomes embodied leadership.
Every No Matter What Adventure follows a universal rhythm. The journey from the known into the unknown and back again. It’s a process that has guided heroes, leaders, and seekers for centuries: a crossing of thresholds, a shedding of what no longer serves, and a return with something new to give.
This isn’t just a travel experience. It’s a lived process of becoming the kind of leader who can navigate the unknown, within yourself, your team, and your organization, no matter what.
