We’re so proud to bring you a beautiful collaboration from a passionate and talented crew! Each of these women has forged her own path and experienced her own transformation, and we’re delighted to have them be part of our experience. They will be supporting you in a holistic approach to self-care.

Meet Your Host


Sheryl ott

As a young woman, I moved from my hometown in rural Oregon to New York City on a dare and ended up with a successful, thriving life and career. I met + married my dream man, rocked it at work, and felt like I was living the dream.

After a move to San Francisco, I left the corporate world to take care of my precious babies, but in what felt like no time at all, my babies were no longer babies.  As they started to grow up and leave the nest, I realized I was staring into my own unknown future. I missed the bold Sheryl from New York! I felt out of touch with the person I once was, living on a dare in one of the most exciting cities in the world. Even though everything on paper was wonderful in my life - fabulous family, amazing community, and beautiful home - this time of transition was truly unsettling.

In hopes of finding what was next for me, I ended up on a women’s hunting retreat in Texas, and instantly felt the spark of connection with my younger self, the one who was courageous enough to move to NYC on a dare. And it was thrilling to reconnect with that bold part of myself again. 

I realized that I had far more grit and gumption inside me than I remembered. I felt a bold awakening from the experiences I had on that trip, but when I got home, my family didn’t quite know what to do with that transformation in me. I felt triumphant at my newfound courage, but was challenged in how to share that with my family and friends.

I knew I wanted to create something equally wonderful and transformative for women, but with a kind of support to help women navigate the entire experience, not just the “trip” -- starting before the trip begins, and offering continued support upon the return home. This retreat, my friends, is just that. We’ll be rallying around you before, during, and after the Dare to Detour weekend, because we know firsthand how important it is to hold onto the authenticity we discover within ourselves.

I’m so looking forward to meeting you. 



Whenever I get together with Sheryl we hit the trail or a cafe and dive right in. That’s Sheryl. She dives right in. As she launches Dare to Detour I can’t be more excited to watch her share her dreams and drive to create an extraordinary life and share that exploration with others. I have always known Sheryl to be a dreamer with a quick wit and a desire to understand life’s twists and turns. But she is not just a dreamer or a questioner, she is a resolute badass, who knows how to get things done. The combination of Sheryl’s tenacity and her sense of wonder always brings a smile to my face and before we part ways, there is always a plan for our next adventure.
— Jessica Gerber, Regional Leadership Director, The Brady Campaign to Prevent Gun Violence

Your Coaches


Laura Riordan

Laura will help you rediscover what lights you up, clarify what makes you tick and map your targets with practical instruction on how to get there. With a Ph.D. in Psychology and 20 years in the mind & body wellness industry, she brings wisdom, clarity, and swiftness to her coaching practice. She is interested in digging deep into passions that might have been forgotten and realistically tying those threads together. It is through this connected narrative that her clients can feel “in tune” with themselves again. For this retreat, Laura will focus on helping you to integrate what you’ve learned back into your daily life.


Linda Lesem

Linda will help you take a deep look at your whole person, identify strengths, navigate crossroads, and brain storm future possibilities. As a career counselor, trained therapist, and certified life coach, Linda specializes in Positive Psychology, the scientific study of optimum living and happiness. Linda works with a range of clients in her private practice, as well as creating and leading curriculum and workshops to help her clients pursue their next best steps. Linda will be leading our group sessions during the retreat.


Your Crew


nicole gianni

The talented Nicole Gianini, founder of Siren Salon and Apothecary in San Anselmo, California, will be on hand to help you redefine your look for the new stage in your life, no matter what that means for you. She has a keen eye for beauty and style, and will work with you to help the outside reflect the inside. Every attendee gets a 30-minute consultation with Nicole, and a digital lookbook to help guide you when you return home.


cassidy wendell

Cassidy Wendell is a wellness writer, online educator, and community builder for people all over the world. Like many, she found her calling in a very roundabout way after losing her dad to a serious stroke in 2013. As a way to express her stress and emotions, she started a blog and soon found an exciting and meaningful career path in the digital space. 

Cass believes That community plays a huge role in professional and personal success.

With this notion at the forefront, she's now a full-time blogger, social media consultant, and brand strategist based out of Bozeman, Montana. Cass will be with you every step of the way during your time in Montana to make sure everything flows as it should.


kait costanti

Kait Costanti, Owner of BASH , a full service event design/production company + alternative bridal shop, is always up for an adventure [often times with her husband and two dachshunds, Hillshire and Finch!]. Having traveled all over the world in locales such as Africa, Turkey and Nepal, her designs are informed by her experiences and individual style. She lives in Montana but grew up on the beach in Southern California where relaxed surfer vibes were ever present. She will be guiding you through a Shibori dying workshop which reminds her of her hometown, Cardiff by the Sea, and can't wait to see your creations!



Kate Murphy is a certified Foundation Training instructor, kinesiologist, bio mechanics and wellness guru, and the founder of Health Revolt.

She has worked twelve years as a personal trainer. For seven of those years she wrestled with chronic pain, failing to find relief on the symptom-chasing treadmill of conventional health care.

During her journey to find relief she spent thousands of hours researching and consulting with leading fitness, nutrition, and wellness experts. She truly believes that we don’t have to settle for a life of adjusting to our symptoms and rearranging our lives around problems we’re told have no solutions.

The answers and freedom Kate found drastically changed her life and now it's her passion and purpose to help other's change theirs.


Monica Michael Willis

Editor and writer Monica Michael Willis has spent 25-plus years as a magazine journalist. She was the features director at Country Living, and has written for dozens of consumer magazines, including Martha Stewart Living, Real Simple, HGTV, Food Network, Parent & Child, and Everyday with Rachel Ray. She is currently the editor at large for ModernFarmer.com, where she edits the news section and spearheads the publication’s food coverage.  In addition to covering travel, design, and the culinary landscape, Willis has written extensively about the environment and the many conservation issues facing us as a society. In her writing workshop, Willis will prompt participants to use honesty and humor to cultivate their distinctive voices and gain insight into the experiences that have shaped and defined them as friends, mothers, partners, and women of the world.


Lo Magee

Lo Magee is a Tennessee native who planted her roots in Montana two years ago. To her, photography is about telling stories - the joys and details of life that shouldn't be missed. This is exactly what she plans to capture at Dare to Detour. When she isn't taking photos, you can find her with her gracious husband and pups on some sort of adventure. 


kimmie geer

Lover of coffee, skiing + adventure, Montana quickly became the dream home to Kimmie Geer almost ten years ago, when she moved from the Pacific Northwest for a college experience in the mountains.

Her love of photography has unfolded through her career in digital marketing. Capturing authentic human emotion brings her pure joy, and she is thrilled to come along on the Dare to Detour journey with you all and do just that.