Give Yourself Space to Tell Your Story
My Weekend with Cheryl Strayed
I was a little intimidated when I walked into a room at Omega Institute filled with over 300 people (and 700 additional attendees from around the world on Zoom) for the Wild Awakenings writer’s workshop led by the best-selling author, Cheryl Strayed.
My goal was to gain insight and tools for making my writing more engaging—specifically with challenging topics. Cheryl wrote the best-selling memoir Wild, about her personal journey through grief on the Pacific Crest Trail.
During the weekend workshop, I started to realize that Cheryl had a lot more to teach me than just writing.
It was evident that Cheryl is a rock star in the publishing and podcasting world. In addition to her gigantic fanbase, “Woos” from the crowd echoed throughout the weekend. She wrote a best-selling and beloved memoir. She’s an experienced, passionate, empathetic writing instructor with an MFA from Syracuse.
But what impressed me most was her down-to-earth personality and approachable spirit.
Throughout the weekend, Cheryl shared stories about herself with an openness that I rarely experience in the world. She views writing through wounds of tragedy as a source of power. While I have found writing helpful over the decades, I had never seen it as a source of personal power. She inspired me to want to write about the suffering, trauma, and loss that I had been avoiding.
The weekend was full of her lectures, 15-minute writing prompts, paired sharing, and readings from audience members for each assignment.
The stories we shared—about pain and suffering, redemption and triumph—were some of the most empowering I have ever heard. One that continues to resonate came from a woman who shared her experience of watching her husband withdraw from her. He refused to do simple chores, such as trimming the trees that were overtaking their house and blocking their view of the valley below them. One day, her husband left for work, leaving a note that he wouldn’t be back.
Through the grief that followed, the writer learned to use their electric saw and cleared the view herself. She could—once again—see the gorgeous valley below.
Her story made me laugh and cry within minutes. These intimate stories, these moments in these writers' lives, made me feel a connection that I hadn’t felt in years, particularly since the pandemic began.
“After nourishment, shelter, and companionship, stories are what we need most.”
I was reminded that a former mentor encouraged me to share personal stories in my first leadership role. But I resisted. I didn’t enjoy sharing my unhappy childhood. Rather, I focused on overcoming past baggage. I preferred not to share the past with others.
However, I did finally share that I was hired to work in the Goldman Sachs talent management group because I had been a former top amateur tennis player and that I had worked with juvenile delinquents as a therapist. My colleagues were impressed, whereas I viewed my experiences with embarrassment since most of my co-workers came from Ivy League schools and prestigious internships. It took me until my early 50’s to get comfortable sharing my stories. This is not easy or comfortable for most of us to do.
And, yet here was Cheryl telling us:
Vulnerability is strength. It’s courage on the page. Dare to show us your wildest self.
(It’s) not who you are, but who you REALLY are.
Aspire (for) credibility, not likeability.
These exercises made me nervous. Yet when I wrote and shared my story with a partner, I felt better and more connected to others— and to myself.
On Saturday over lunch, a fellow participant shared that they were training their leaders at her company on storytelling as a way to help reconnect people after the pandemic. That struck me as a wonderful idea. If there is ever a time we need heartfelt stories, it is now.
That’s when I realized what Cheryl’s writing class was really about: living and leading.
What if I could start owning my writing instead of feeling embarrassed? I had never viewed myself as a writer. What if I could, instead, view my writing as something that is teaching and informing me, making me better at everything I do—as a tool for sharing a piece of myself?
Good writing opens up those vulnerable places. Just as a strong leader is willing to be selectively vulnerable. The more you can show your true self, the more others can relate to you. You certainly need boundaries, but as a writer, you are in control of what you share. You are in control of the story.
And you decide what criticism to accept.
This was another eye-opening moment. Oftentimes the biggest fear of sharing something personal is the potential for it not landing well with or being rejected by the person receiving it. It reminds me of dating (the worst part of dating). But, like dating, if that person holds no value in your life, you don’t have to accept their criticism.
Most of us think we have to accept and react to the criticism others give us, but once you realize that only you are in control of what you accept, the feeling you are left with is lightness and freedom. Rejection, loss, and imperfection are part of the learning process. Many of us have these imposter or rejection fears. Instead of avoiding them, welcome them in! Just don’t let them drive the bus. Take ownership. Don’t relinquish your power to the outside world. Don't let your fears of writing something awful stop you. Perhaps that is the key to being a good writer. Better yet, perhaps that is the key to being good at anything.
I returned from Cheryl's workshop a little braver and a bit more confident. From here on out, I am calling myself a writer. I am writing stories that involve feeling pain or embarrassment, and I am telling those stories more in my work as a coach. It doesn’t always feel comfortable, but I am no longer waiting for it to feel easy—since it may never feel comfortable.
It’s up to us to tell our stories—I hope you’ll join me in telling yours.
“You can’t wait for inspiration. You have to go after it with a club!”