VAIL, COLORADO · SEPTEMBER 24–26
No Matter What
Adventure Retreat
2 MONTH CONTAINER
Pause with purpose. Return with clarity.
2.5 day in-person retreat. For leaders ready to step away from the day-to-day, gain perspective, and prepare for their next season of growth.
2.5 Day Immersive Retreat
Vail, CO
September 24-26, 2026
"Keep close to Nature's heart, and break clear away, once in a while, and climb a mountain or spend a week in the woods. Wash your spirit clean."
— John Muir
The thing holding you back probably isn’t what you think.
During Colorado’s peak aspen season, you’ll step outside the noise, challenge yourself physically, and discover what’s actually driving your decisions, your results personal and professionally, and your next level of growth.
You’ll leave with a breakthrough: an understanding of the pattern that’s been limiting you, clarity during transition with tools to lead differently and a commitment to what comes next.
At a Glance
The Experience
Adventure Retreat: 2 Month Experience
Where
Vail, Colorado
Dates
September 24–26
Format
2 Month Experience. 2.5 Day In-Person Retreat
Hosts
Sterling Hawkins and Haviland Hawkins with special guests Ericka Jones · Tony Videen
Payment + application:
By registration + application acceptance only
THE EXPERIENCE
More than a climb. You’ll leave with.
Thursday we arrive. Friday takes you deep into the unknown. Saturday brings you back home.
“The unknown isn’t what stands in the way—it’s the path itself. Every step into uncertainty is a step into leadership.” - Sterling
YOUR HOSTS
Spending two days with the people who built this.
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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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Tony has always been a creator at heart. You can see this in the businesses he’s started in design, construction, and real estate, and in his drive to build community. No matter if he’s working on a home, an event, or a company, he’s always asking the same question: what’s truly real here, and how can we build it together?
That question led him to his latest and most uncertain adventure: co-founding a start-up in the AI space. He’s now working to help bring the resistant construction industry into the tech age.
Walking the Path Himself: Tony loves spending time in the mountains and brings that same spirit to his life. For most of the past decade, he’s explored the Rocky Mountains of Colorado, enjoying nature, fresh air, quiet moments, and trails that reveal what really matters. The mountains help him reflect on what’s real for himself, and he’s just as interested in discovering what’s real for others. On the trail, Tony offers a calm presence, honest conversation, and a playful energy that helps keep everyone grounded when things get tough.
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Ericka believes that everyone has a unique spark, and when we embrace and share it, everyone gains. One of her guiding philosophies is, "I'll take care of me for you. You take care of you for me." She encourages lifelong learning and personal growth so we can become our best selves. When we focus on our own development, we help organizations grow, support healthier communities, and create a more connected world.
Building Cultures Where People Thrive: For over 20 years, Ericka has worked with Fortune 500 organizations to strengthen leadership, shape culture, and align social impact with business strategy. Her expertise spans organizational culture, Diversity, Equity & Inclusion, leadership development, talent strategy, recruitment, and community impact. She helps leaders create inclusive workplaces by embedding the systems, practices, and leadership behaviors that enable individuals and businesses to thrive.
Awakening What's Already Within: Whether Ericka is working with executives, teaching yoga/meditation, or leading community experiences, she brings together coaching, mindfulness, movement, and real conversation to help people reconnect with their inner spark. She believes that when we slow down, heal, and connect more deeply with ourselves and others, that spark can inspire more compassionate leadership, stronger relationships, and healthier communities. Through her work, she invites others to lead from within, with courage, joy, and integrity.
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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. And spending time with her dog, Asher.
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.
THE CONTAINER
This isn't 2.5 days. It's a 2-month container, designed to hold real change instead of a single, forgettable weekend.
Most retreats give you a high and hand you back to your regular week with a memory and mild jet lag. Whatever surfaced when the phone was off comes back into contact with the same email inbox, the same team, the same patterns, and it fades in about two weeks. That's not a failure of you. It's a failure of design. Two and a half days on a mountain was never going to be enough on its own.
So we didn't design a retreat. We designed a container: two months, three phases, one arc.
Before you arrive | A kickoff call with the full group, so nobody starts as a stranger. Weekly guided meditations and a short workbook to get you present before you land in Vail. A 1:1 check-in with a facilitator. A growth partner assigned to walk this with you, not just alongside you.
On the mountain | The two and a half days you've read about above. This is the container's most intense moment, not its entirety.
After you leave | An integration workbook built to carry what surfaced back into how you actually lead. A closing call with the full group. Ongoing check-ins with your growth partner, so the insight from the mountain has somewhere to go once you're back at your desk.
The climb creates the opening. The container is what makes sure it doesn't close the moment you're back in range of your phone.
THE INVESTMENT
Everything is built around one thing: getting you fully present, without the logistics getting in the way.
Everything is built around one thing: getting you fully present, without the logistics getting in the way.
Limited spots total · this exact group, on this exact mountain, doesn't happen again
- Full day of mountain guides
- Three Dinners and lunches
- Gravity Haus wellness access — yoga, sauna, cold plunge
- Pre-climb Zoom session with the full group
- Weekly guided meditations leading up to the retreat
- Weekly workbook to prepare before you arrive
- 1:1 check-in call with a facilitator
- A growth partner throughout the experience
Registration holds your spot, balance due 30 days before the retreat. Or pay in full today.
Registration closes for good on September 4.
The aspens peak for about three weeks a year. This retreat is timed to that exact window, there's no version of this where the date moves and it looks the same.
WHY NOW?
You don't get a version of this year twice.
Vail's aspens peak for two weeks a year. Miss this window, and it's not a delay, it's another full year of the same routine.
limited Spots
These retreats are intentionally small. Once the spot is gone. The spot is gone.
Sept 4
Registration ends. Step away. Step outside. Step into the unknown. Then come home differently.
Once those seats and that date are gone, this exact group, on this exact mountain, doesn't happen again.
“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.”
IS THIS FOR YOU?
This Is For You If…
You feel a pull toward something more, and you want to answer it — no matter what.
You're willing to do a hard thing on purpose, even when it would be easier not to.
You believe real connection happens when people stop performing and start being honest.
You want to grow the way the aspens do — a whole grove, one root system, nobody standing alone.
You can give two full days to this, and really mean it.
This Is For You If…
You want easy, not real.
You'd rather check your phone than watch the sunrise.
"No matter what" sounds to you like just something people say.
You can't be away from work for two days right now.
You're not ready yet. That's okay — this will still be here.
Frequently Asked Questions
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Submit your application and payment to reserve your place.
After your payment, you will get a link to a written application to complete. Once your application is reviewed and accepted, your registration is confirmed.
If you're not accepted, your payment will be refunded in full.
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The loop is 9 miles with real elevation gain over about six hours. You don't need to be an athlete, but you should be a regular hiker or comfortable on your feet for a full day outdoors.
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Lodging, meals outside what's listed, and getting yourself to Vail. We'll send lodging recommendations near Gravity Haus once you register.
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It's not a retreat about feelings for their own sake. It's built to surface the one leadership pattern that's currently capping your team's growth, the kind no boardroom conversation reaches, and give you a concrete way to operate differently starting the week you're back. The mountain is the mechanism. The business result is the point.
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That's most people. Day One exists specifically so nobody starts the hike as a stranger.
Ready to lead into the unknown?
This retreat is by application only. Reserving your spot with payment starts the process, it isn't automatic acceptance. If you're not accepted, you'll receive a full refund.
If you've been waiting for a sign to get out of the office and into something real, this is it. This program is by application only.