Climb Higher. Grow Deeper. Lead No Matter What:
Grays Peak
No Matter What 1-Day Growth & Leadership Immersion: Grays Peak (14,278 ft), Featuring Special Guest
1 Day Immersion
Grays Peak, Colorado
September 19, 2026
Union of Opposites
Grays Peak (often paired with its twin, Torreys) embodies the paradox of partnership. Two distinct paths converge toward a single summit, separated only by a short, rugged saddle.
This mountain teaches that growth often comes through tension, the reconciliation of difference within ourselves and with others. For Indigenous peoples, twin peaks represented harmony between masculine and feminine energies, or between seen and unseen worlds. To climb Grays is to cross that threshold: from separation to integration, from competition to collaboration.
Special Guest
Greg Scheinman
Founder, Midlife Male · 25,000+ weekly readers
This Grays Peak immersion is joined by a guide whose work is built on real-world transformation under pressure.
Greg Scheinman brings decades of experience helping leaders translate challenge into clarity and discipline into lasting change.
A serial entrepreneur with two seven-figure exits and the founder of Midlife Male, Greg has interviewed 200+ high-performers and coached 100’s of individuals and teams through meaningful reinvention. His work is grounded not in theory, but in lived experience, having navigated panic attacks, addiction, profound loss, and the hard work of rebuilding from the inside out.
On Grays Peak, Greg joins as a co-guide with the No Matter What Team, walking the ridge alongside you, deepening the practice of integration, steadiness, and trust when conditions shift.
“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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Integration | Bridge inner and outer alignment
Grays and Torreys sit side by side, connected by a narrow ridge. Crossing it makes something clear: leadership works best when your inner values and outer actions stop pulling in different directions. This climb helps close that gap, so how you lead matches who you are.
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Partnership | Strengthen collaboration through discomfort
Partnership isn’t built in meetings. It’s built when things get hard. As the trail steepens and energy drops, you’ll experience what it means to rely on others, and be relied on. The mountain shows how trust and collaboration grow when you move together through challenge.
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Balance | Harmonize action and reflection, drive and stillness
The climb requires effort, but it also demands awareness. You’ll move forward, stop, listen, adjust, and move again. Balance here isn’t about slowing down, it’s about knowing when to act and when to recalibrate, without losing momentum.
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Trust | Deepen relational leadership
Trust isn’t a concept on Grays Peak. It’s built step by step, through shared effort, honest presence, and navigating uncertainty together. You’ll feel how trust forms naturally when people show up fully and move forward as a team.
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:
September 19, 2026* Date subject to change with weather
Location:
Colorado Front Range — (Grays 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
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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.
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Greg Scheinman helps men take full ownership of midlife. A serial entrepreneur with two seven-figure exits – Insgroup (acquired by BRP/NASDAQ) and Team Baby Entertainment (acquired by Michael Eisner) – Greg now leads Midlife Male, a platform reaching 25,000+ accomplished men weekly. He's interviewed over 200 high-performers and coached more than 100 individuals and teams from mediocre to maximized.
Greg's also lived the lows: panic attacks, depression, alcoholism, and profound loss. Through it, he built a proven operating system for transformation – from fat to fit, drunk to sober, broke to wealthy, rudderless to purposeful. His approach isn't theory. It's tested daily and featured in Men's Health, The Wall Street Journal, and The New York Times.
At 52, Greg's in the best shape of his life: two-time D10 Decathlon winner, third place at HYROX Nationals, and a regular at 29029 Everesting and Spartan races. He's an ISSA-certified trainer, CrossFit L1 coach, husband of 24 years, and father of two sons.
Proven Transformer: 30 years turning setbacks into systems that work.
High-Performance Realist: Creator of the 5 Rules, 6 Fs, and 1 Question framework for midlife mastery.
Competitive Athlete: Competes in endurance events and lives the habits he teaches.
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.
This deposit secures your place in the Grays Peak No Matter What Immersion.
This experience is intentionally small and commitment-based. Your spot is not confirmed until the deposit is received and your application is submitted.
After submitting your deposit, you’ll receive:
Please schedule your brief interview call SCHEDULE
Next steps and preparation details will then be sent upon acceptance along with required forms and logistics information
If you have questions or need a custom payment arrangement, reach out to haviland@sterlinghawkins.com
Your payment includes a credit card processing fee. If you are not accepted, you will receive a full refund.
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.
