16 minute read
Sheryl Ott: Finding Freedom Through the Detours
by Lauren Burgess
images by Danielle Lopez & Devin Helen Archilla
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I can see Sheryl Ott sitting in her new kitchen, gazing back at me through our Facetime call with focused, engaged energy scarcely less tangible than when I see her in person. Her sweep of golden-gray hair glows in the low-angled morning light of late November. It teases into a curl where it kisses collarbones and crowns the soft curve of breast, subtle reconstructive surgical scars hidden beneath a neutral-colored, chunky knit sweater. She tilts her head and smiles through blue-light glasses, a subtle coyness grounded by the substance of her honesty and wit. She speaks of the newlyhung bird feeders outside her window, and I imagine two words held close in her palms as if they are themselves delicate birds— crushed if held too tight, yet in danger of being released before their time. Divorce. Breast cancer. Then, unafraid, she sings each word into the song of our conversation, part of her life that sweeps up both those shadowed truths into a full, achingly beautiful symphony.
This moment in time feels somehow separated from reality, juxtaposed against how I know Sheryl best: kicking up her boots in the sunshine at a historic ranch in southwest Montana, inhabiting her surroundings with a cool, casual elegance, breathing in the wind with power, purpose, and a ready smile. We met when Sheryl first extended an invitation to me, sight unseen, to be part of her Dare to Detour retreat. The image of Sheryl leading Dare is how I hold her in my mind. Passionate. Joyful. At peace. But this moment, while foreign— as we sit separated by a screen, hungry for the sense of grounding and connection that have been many months out of reach— is just as real. At this moment, we collectively and individually feel our souls exposed to the elements, cast out from the comforts in which we’ve taken solace for so long. For Sheryl, it’s been a crucible of transformation. And she would not just survive, but— perhaps for the first time— wholeheartedly thrive.
Sheryl carries cool within her bones like a mountain stream. If I closed my eyes, I’d let her words flow over me like the mist from a waterfall. Her energy is so expansively real that I can feel it emerge from the screen’s pixels and shift the aura of my home office; there’s just something in this woman that wakes the spirit. She reminds you of your better self, who you were, and who you could become. A few minutes with Sheryl will have you belly-laughing while reconnecting to your power and purpose. She doesn’t do this intentionally— it’s simply what she lives, emanates, and shares. But today, we’re not laughing—we’re grieving the part of herself that Sheryl leaves behind as she recognizes that she was only ever meant to climb the mountain, not to carry it.
image by Danielle Lopez
With that heart-on-her-sleeve, matter-of-fact way of sharing that disarms the listener with sincerity, Sheryl describes her week to me, and the words hit deeply. “I just decided not to visit my family for Thanksgiving. I’m feeling tremendous grief right now, on so many levels, but I didn’t fully realize it until I had to tell my parents I’m not coming. My 81-year-old mom, this dear woman who’s never dropped an f-bomb in her life, responded, ‘F*ck covid.’ My dad said, ‘Dear!’ and then she said it again. I won’t see my parents anytime soon, I haven’t seen them in a year, and I won’t be with my kids, either, so there’s that.”
In 2020, a year of upheaval and loss, Sheryl inhabits a uniquely liminal space in both the physical world and the world of the heart. She recently left the expansive landscape of the Bridger foothills for a downtown Bozeman home. With it, she released the closeness and restriction of a dying marriage for the promise of independence. The house is smaller, but entirely hers. She explores every inch of her new home in parallel with plumbing the depths of her soul, experiencing both with tender realness— new beginnings wrought by possibility and pain. “When I say I have layers of grief, I’m grieving the loss of the woman who I was. And I’m celebrating where I see that woman heading.”
Sheryl’s life has been defined by new beginnings, both chosen and unexpected. She recalls her last childhood memory of feeling freely, utterly herself, around the age of ten. And then, “as I grew up, comparison crept in. I’d loved volleyball in middle school but failed to make the cut for the high school team, and I let that failure define me. And that is when I first put the mask on. So, instead of doing things for the love of it, out of curiosity and joy, I began following the path of least resistance. I started to bury my inner child’s spirit of creativity and adventurousness under the burden of what was expected of me. I threw myself into the role of being ‘good.’ I was the good student, the safe driver, the cheerleader, student body secretary. I became— and remain— adept at reading a situation and adapting to it, good at meeting expectations. And whether or not those expectations were healthy, or anything I wanted, didn’t matter. I was driven by external affirmation. I think most people mean well when they place their expectations upon you— but that doesn’t really matter in the end, when it subdues the soul.”
“College was my first real open door to freedom. I took the mask off, but that is a risky moment of vulnerability— you’re at risk of just slipping on a different mask. I was so young when I went to college, just 17, and not emotionally equipped to stand in my own power, still seeking external affirmation. I didn’t pursue a major I loved, just whatever would get me through on time, to stay in keeping with my parents’ wishes that I’d graduate in four years.”
But despite the decades of serving others, of defining her success by the voiced and unspoken expectations of those around her, Sheryl has always had a spark of rebellious, courageous fire within. It’s come out in ways over the years— bucking the expectations of becoming a navy wife to her college boyfriend, and instead, moving to New York City by herself to pursue a career in the financial industry. Applying to over 100 jobs and enduring rejection from all but two. Going up against blue-blooded ivy leaguers for interviews, armed with a state school education funded by a 4-H scholarship and a walletful of tips earned as a nighttime truckstop waitress. Carving out her niche at the first online trading company in the world, and then in investment banking, where she met her future husband.
Together, they moved back to San Francisco, where Sheryl tried to continue her thriving career, but job after job turned her down because of her visible pregnancy. She threw herself into caring for her children. She was happy, mostly, but found identity almost solely in being a parent and a wife.
Eventually, she abruptly transitioned from stayat-home mom of 18 years to empty nester. She’d defined herself by her career, then motherhood. And now, the doors and windows were wide open. The nest was empty in more ways than one.
“It was groundless. I felt like a hot mess, and I wondered out loud, ‘What happened to the brave girl who moved to New York City on a dare?’ As I struggled with finding purpose and meaning, I realized my North Star has been there all along; it just required a detour. I needed to go in a new direction: back to myself. It all came rushing to me at once. I was going to Dare to Detour, and take other like-minded women with me.”
image by Devin Helen Archilla
What she did then has rippled outward to impact women from different backgrounds and situations, with unique stories but the same questions. Who am I, beneath outer expectations? How can I liberate that part of myself and connect with who I am now?
Sheryl’s story, in many ways, feels like the eternal story of being a woman. Our true selves, vibrant and free in childhood, become stifled by expectations, woundings, heartbreak, and fear. So we let the course of our life flow down the safe path, the beaten path. We are ruled by “shoulds” instead of passion. We spend time listening to outer critics, but the most powerful criticism of all often comes from within— the voices and stories we internalized and the masks we now use as a means of self-preservation. And yet, the “self ” we’re protecting may be far from who we actually are— we’ve worn a mask for so long that we don’t even know who’s beneath it.
But still, we feel a sense of longing, a feeling that we are meant for more. The greater the ache, the larger the disconnect between our masked self and our true self. Eventually, we reach a point where remaining the same causes greater discomfort than the vulnerability of change. That moment is where our detour begins.
In 2018, Sheryl created a community of inspiration and transformation. Dare to Detour is an in-person retreat held each fall at the Nine Quarter Circle Ranch in southwest Montana, adjacent to the ruggedly beautiful Lee Metcalf Wilderness. Women join together for five days in an empowering exploration of their own hearts. The retreat has grown over the years, with more participants coming, others returning, and an infusion of increasingly poignant exercises and retreat offerings. I can say firsthand that Dare to Detour supports women in realizing their strengths, resilience, and creative potential.
And why Montana? We give the feelings different names, but the meanings run deep, parallel with one another like long lines of ancient strata. Freedom. Possibility. Untaming our wild hearts. When we feel our little human bodies pressed against the stoic grandeur of such powerful wildness, we feel at once grounded and uplifted. A simultaneous departure from the known and a return to what we somehow knew all along. An invitation to explore who we are beneath the distraction of societal or familial expectations. There is nothing as freeing as the moment we lean fully into the bracing clarity of the wild mountain winds of Big Sky Country, with the knowledge that nothing looks back to judge us. We feel only openness and truth, connecting with something larger than ourselves and stepping wholeheartedly into the purity of the expanse. The only requirement to entry, perhaps even to enlightenment, is that our mask be left at the trailhead.
So, Dare to Detour began to take off. Sheryl Ott was invigorated with the success of her third annual retreat, poised to bring Dare to a new reach of influence. And then, the world crashed down around her with devastating news. Breast cancer.
A family history of breast cancer had motivated her to do regular self-checks and screenings since the age of forty. For over a decade, the results were silent. Healthy. “Finally, last year, the screenings revealed a tumor. It was Grade 1, which meant slow-growing, less aggressive. But still— cancer.”
image by Danielle Lopez
Over the next six months, Sheryl pursued an aggressive treatment plan. On March 16th, as the world entered pandemic lockdown, Sheryl courageously underwent a double mastectomy and reconstructive surgery. And as she recovered from surgery, learning to self-advocate and care for her changed body in the midst of a global crises, the threads of her twenty-five-year marriage unraveled in her fingers. "We had been struggling for a long time, and we'd hoped moving to Montana, a fresh start, would bring the two of us back in alignment. But it did not. It's profoundly sad. We'd become too isolated from one another—we were too different in our identities and our paths."
In late summer, they separated. Sheryl said, “I had no idea how much my confidence had been impacted over the years until I walked away. I feel very vulnerable… a word which is up there with ‘self-care’ right now. To be vulnerable carries deeper meaning and heartache than most of us give it credit for. Let’s not just throw that shit out there— ‘be vulnerable’— unless we’re really willing to do it. To be terrified, sitting in a space of grief and sadness and uncertainty. Yet with all of that heartache, vulnerability is so essential in starting anew. Learning to be comfortable with my whole self may be my most significant opportunity right now. Just showing up every day, messy but real. I’ve never allowed myself to be this real before.”
“When we talk about new beginnings, there’s a lot of optimism and excitement, but with that also comes grief. Grief because you’re often leaving something behind, or recognizing that something may not have happened in the way you’d hoped. I’m in a season I never expected. And when this began, I knew it’d be hard, but I didn’t know how hard. I have been fortunate in my life to not have felt lots of grief… but everything that happened in the past, and is happening now, I’m feeling that grief, all of it at once. It’s f*cking hard! But I want to feel the full spectrum of these emotions because it’s a privilege for me to know all of this— even to feel the heartache. I could have been given a very different diagnosis. My cancer could have taken a very different path. I could have been in a different situation, where I wasn’t able to treat it aggressively or advocate for myself. But here I am, cancer-free. And I truly feel like I have a second chance in doing things well for myself and my kids.”
image by Danielle Lopez
The losses of those parts of her identity, her body and soul, have opened the door to a renewed sense of authenticity. Sheryl told me, “Detours like these— my breasts, my marriage— it’s a deeply vulnerable position. But there’s an opportunity for a new beginning in every detour. In a way, I’ve been given the greatest gift: the chance to start over. Each morning I wake up and go through everything I’m grateful for. My new health. My children. My people. My resolve. When we’re in the middle of challenging times, we might not notice that we’re building our resilience, little by little. But once we step through the door of a new beginning— bravely acknowledging our transformation— we can flex those resiliency muscles, illuminate our purpose, and feel truly free.”
“For my entire life, I was out there interacting with a mask on. And taking it off was so hard. It’s not just about what others see— it’s about what I see in myself. Where I find myself now, I’m starting to feel fully capable of keeping the mask off this time. It feels good to my nervous system. I’m not looking back over my shoulder wondering what someone’s thinking, if they’re judging me, if I’m being scrutinized. I haven’t had that in so long, I can’t even remember. It’s so freeing.”
As I listen to my friend share her lived wisdom, I think about my own mask. Removing it is terrifying because it brings not just a fear of rejection, but the danger of being rejected for who we truly are. Yet, if the mask remains, we never have the opportunity to be seen. Masked, we will always feel starved for love, acceptance, and safety, because it cannot genuinely be ours.
Oprah Winfrey
When Sheryl was first diagnosed with cancer, she wrote down the five things she feared the most. Her fear of heights was at the very top of the list. So, in August, she went skydiving. She incorporated the adventure as part of a DIY Detour Challenge series she hosted during the pandemic, in lieu of an in-person retreat— she wanted to conquer her fear, and invite other women to conquer theirs, too. Sheryl and her daughter Isabel sat in a small plane, harnessed to complete strangers, and flew to an elevation nearly 10,000' above the valley floor.
I believe this moment was the manifestation of Sheryl’s truth. The tipping point at which being anything but her authentic self felt too small a life to live. At this moment, she craved truth above all else, stepping into the unknown of who she could truly be. Flying high above the earth, with no expectations, she was driven wholly by joy and trust in the creative universe. Her deeper self, wild child, daring seeker of adventure, that strong, brilliant being within, was ready to reemerge.
image by Devin Helen Archilla
The instructor opened the door. Sheryl stood upon the small struts of the plane, leaned into the wild winds… and let go. She jumped into the void.
As the atmosphere rushed past, all those hidden burdens, the tendrils of expectations, the narratives which did not serve her, were stripped away and released into the vast blue. All that remained was her. She was weightless. Utterly free.
“I gave myself the gift of presence, letting go and trusting fully. When people talk about the act of trust as you step into the void— that’s exactly what I did. And diminishing the fear we feel, trying to negate it, doesn’t actually serve us. We can simply acknowledge it and let it naturally drop away as we move further into the unknown, into the truth.
Because what’s out there, ultimately, is me. My true self. That’s what’s waiting. And that is the most worthy, wonderful gift, the best existence possible.”
. . .
LAUREN BURGESS is a sincere listener, creative optimist, and plucky adventurer. Seeking the connective threads between the everyday and the sublime, she writes from lived experiences— on foot, with hands, and from the heart. At the helm of First Light Writing, Lauren creates everything from website copy for neighborhood startups to organizational brand strategies; ad one-liners to multi-million-dollar fundraising campaign themes. Her philosophy is that marketing should be meaningful— how we tell our stories can change our world for the better. A chronic dabbler and exuberant neophile, Lauren takes pride in her non-vocational titles: wife to a man who always knows how to make her laugh, dog mom, cheerful ultrarunner, intermediate whitewater rafter, rookie ice climber, and aspiring mandolinist. The quickest ways to her heart are fresh-baked bread, good storms (with good gear), a sung harmony, or a starry night sky.
image by Danielle Lopez
