The Counterintuitive Advice Author Cheryl Strayed Gave About Achieving Greatness

Cheryl Strayed is a New York Times bestselling author whose work has been translated into 40 languages around the world and whose memoir “Wild” was turned into an Academy Award-nominated film starring Reese Witherspoon.

Yet when she was just getting started, she found her ambition paralyzing.

To be great, Strayed first had to get over wanting to be great.

When Strayed talked to entrepreneur, investor and author Tim Ferriss in Austin for the South by Southwest Conference & Festivals, she revealed that if she could put any phrase on a billboard, it would be, “Surrender to your own mediocrity.”

She recognizes that the advice may sound depressing. But, she insists, it’s liberating.

Early on in her career, “I really felt like, ‘OK, I am going to try to write the Great American Novel.’ Like every writer,” says Strayed. “There is this American idea that you reach for those kinds of heights, and I found when I was about two-thirds the way into that endeavor, writing that book, that the idea of greatness was what was keeping me from fulfilling this dream.”

Strayed had to walk back her own expectations.

“What I had to do was that humble thing: ’Guess what, it’s true, I might be writing a mediocre book. I might be writing a book that nobody ever reads. And I just have to surrender to the truth of that, and I have to surrender to this notion that even if I am mediocre, what matters more to me than writing a great novel is writing a novel. And that was a huge lesson.”

Paralyzed by a desire to write impressive “literature,” Strayed often had a hard time starting to write. She learned to side-step her anxiety by writing whatever portion of a piece she could. That sometimes meant starting to write the middle section and jumping around once she was more relaxed.

Strayed became a mainstream success after Oprah Winfrey selected her memoir “Wild” to be part of her namesake book club. In “Wild,” Strayed heals from the untimely death of her mother by hiking the Pacific Crest Trail. She learns to keep hiking despite painful blisters, to keep moving through disappointment and hurt.

Writing her memoir about the hike was painful, too.

“Did I sometimes cry writing ‘Wild’? Yeah, I would say probably every day. Probably every day. And, was that good for me or bad for me? It was really good for me,” says Strayed. “It is through writing that I have come to understand who I am and what I have been through and therefore who we all are. And that’s really been an emotional journey and one that I am better for having taken.”

In the painful, messy process of working through her own story, Strayed did, eventually, find success.

“What I have found in my journey as a writer, is that even though I aspire to greatness, even though I wanted to make beauty and truth and all those big highfalutin things, the only way that I could do it was to be humble and to say, ‘I am really going to try, and I might fail and I am not going to feel sorry for myself, I am going to be strong in the midst of my humility.’”