Executive Women’s Leadership Retreat
Women Leaders Retreat | Leading with Intention | Jennifer Olson
Santa Fe, New Mexico | April 22–25, 2027
Step away from the pace and pressure of everyday leadership and give yourself space to reconnect, reflect, and reimagine what comes next.
Set at the restorative Ojo Santa Fe Spa Resort, this four-day retreat is designed for women executives and senior leaders who are ready to lead with greater clarity, confidence, and intention. Led by Jennifer Olson and Canyon Calling Guide Emma Lyddan, the experience blends leadership coaching with time in nature, meaningful conversation, creativity, exceptional dining, and space to simply breathe.
Throughout the retreat, you’ll explore courage, curiosity, values, and boundaries, along with leading through change, reinvention, and vision, through facilitated leadership sessions and reflection. You’ll also hike among the dramatic landscapes of northern New Mexico, experience Santa Fe’s art and culture, enjoy spa and thermal pool time, and gather over memorable meals at places including Geronimo, The Compound, and Ojo Santa Fe.
This is not a conference or a packed agenda. It is an intentional pause—a chance to step outside your usual environment, connect with an intimate community of women leaders, and return home with renewed perspective and a clearer sense of how you want to lead.
Highlights include:
- Three nights at Ojo Santa Fe Spa Resort
- Leadership workshops and guided reflection with Jennifer Olson
- Guided hiking and yoga with Emma Lyddan
- Spa, thermal pools, and time to recharge
- Santa Fe art, culture, and creative experiences
- Exceptional dining
- Meaningful connection with other women leaders
- Reflection time designed to turn insight into intention
$3,995
$500 deposit due at sign up, remainder due 30 days prior to trip.
*Trip Pricing does not include airfare, alcohol, or spa packages.
Arrive in Santa Fe by 2:00 PM on April 22.
Depart April 25.
Lead with intention. Return inspired.
The Retreat Experience
Jennifer’s sessions center on four hallmarks: courage, curiosity, values, and boundaries. Each session is paired with unhurried reflection time, so you can ramp down, think deeply, and work through what comes up in the way that works best for you.
Day 1 | April 22 – Arrival, Grounding & Intentional Connection
Arrive in Santa Fe by 2:00 PM and transfer to Ojo Santa Fe Spa Resort. Settle in, then gather for the opening session with Jennifer: Reflection & Intention Setting. Enjoy sunset at the resort, a farm-to-table dinner at Geronimo, and evening reflection and journaling.
Day 2 | April 23 – Leadership & Values
Two longer facilitated sessions with Jennifer, each with built-in reflection time:
- Leadership Through Change – Take an honest inventory of how you are leading. Is it aligned with how and why you want to lead, or is it the “old” you? Are your dreams consistent with where you are, how big is the gap, and what holds you back?
- Values Alignment – What is central to you? Where do your boundaries support your values, and where do they not?
Guided hike with Emma, picnic lunch on the trail, free time for the spa or personal reflection, and dinner at The Compound.
Day 3 | April 24 – Creativity & Reinvention
Session with Jennifer: Identifying Your Impact. Call it impact, legacy, or ROI on life, this is a personal journey into what YOU want to leave behind, what you want people to say about you, and how you want to make your mark. We’ll push beyond conventional norms (and excuses), get creative, and open our aperture. The day also includes a Santa Fe walking tour of art, history, and local artisans, lunch at Café Pasqual’s, a hands-on creative workshop with a local artist, and free time to enjoy the spa, pools, or a final hike.
Day 4 | April 25 – Courage, Vision & Departure
Sessions with Jennifer: Shaping Your Vision with Courage and Building Your “Truth Posse”, the trusted circle who will tell you the truth and champion your next chapter. We close with Gratitude & Grace with Jennifer and Emma before departing for the airport.
Meet Your Retreat Leaders
Jennifer M. Olson, MBA
Strategic Advisor, Thought Leader & Coach
Jennifer is a transformational health executive, award-winning strategist, operator and respected senior leader with over two decades driving enterprise-level impact in complex health systems and more recently, growth stage companies. She is a frequent speaker and thought leader on pediatric and women’s health, prompting colleagues and clients to think about improving health care through curiosity, courage, and transformation, both as an individual and within professional roles. Jennifer’s style is direct, approachable, and intended to drive immediate reflection and results that you can take back to both the home and the office.
Emma Lyddan
Canyon Calling Guide
Emma fell in love with the outdoors at 14 on a life-changing, all-female backpacking trip through the Sierra Nevada. She graduated from the University of Alaska with a degree in Environmental Studies, Geography, and Outdoor Studies, and has guided on Denali and led glacier, kayak, and wilderness trips in Alaska and Patagonia. At Canyon Calling, Emma shares her passion for the natural world, connecting women to the outdoors and to themselves. On this retreat she leads the guided hikes and yoga.
Small Groups, Big Connections
Each Canyon Calling tour keeps it intimate, with 6–12 women per trip. That means no tourist herds, no “flag-following,” and plenty of time to connect.
These aren’t cookie-cutter vacations. They’re immersive, soul-refreshing experiences that remind you who you are outside of your roles.
And something magical happens in these groups…
Women support each other, encourage each other, and laugh until it hurts. It’s like summer camp for grown-ups… if summer camp had hot springs, world-class guides, and way better snacks.
