Cheryl Strayed's "Humble Journey to Greatness" at Oprah's Super Soul Sessions

Cheryl Strayed's "Humble Journey to Greatness" at Oprah's Super Soul Sessions

I had the great privilege of attending Oprah's Super Soul Session Series 2 in Los Angeles over the weekend. I heard spellbinding speakers such as Shaka Senghor, Marie Forleo, Caroline Myss, Amandla Stenberg, Kris Carr, India.Arie, Dr. Shefali Tsabary, Eckhart Tolle, and Kerry Washington. The entire event was moving and inspirational beyond words. But as a writer, Cheryl Strayed's talk particularly resonated with me. 

Her talk was called "The Humble Journey to Greatness," or as she mentioned later, "AKA, Don't Let Your Dreams Ruin Your Life." It's about a trap that a lot of people fall into, artists and creators especially: not fulfilling your dreams. 

At the time Cheryl graduated from her MFA program, she had half to two-thirds of a completed book, but her fear was that she would go back to waiting tables and again her dream of writing would take the backseat. So she and her husband, despite not having much money, decided that she wouldn't go back to work for the year after she graduated. They took on credit card debt for her portion of the bills. 

Even with days of uninterrupted time to write, Cheryl wasn't making progress. She felt the pull of reality TV and was many times sucked into the void, having reached the end of the day without much writing to show for it. 

Reality TV was only in part to blame. She had also placed upon her shoulders the burden of writing the best novel ever written. She wanted to write the Great American Novel, something I myself was pressuring myself to do until recently. 

Cheryl asked us to consider "What happens when we don't act upon our most important intentions? What happens when we do one thing and say another? What happens when we only have ourselves to blame?" 

Or rather, what happens when you pressure yourself into a dream so lofty and unattainable that you nearly give up your dream because the work you produce never feels good enough?

As Cheryl said, "stacks of pages do not add up to a novel. Books require a greater concentration." 

She said that her days alone in her cabin writing her novel were some of the hardest of her life. But there was one thing that kept her going and allowed her to eventually finish her novel: mediocrity. 

"I had to surrender to the idea of my own mediocrity," she said. "Don't remember what it's like to be perfect because you've never been there. Remember what it feels like to reach. When you surrender to mediocrity, you acknowledge that the best thing you can give us is what you already have. Sing with your own voice. That is greatness."

Surrendering to our mediocrity is an act of humility. It requires reckoning with the self. Telling ourselves things we don't want to hear. Many writers have wanted to be writers for their entire lives, and they dream of having impact like that of Harper Lee and Gabriel Garcia Marquez. To admit that we may not ever do that is, in a way, accepting defeat. 

As Cheryl put it, and as all writers have to learn, "You have to ask yourself not who you aspire to be, but who you really are." Writing a mediocre novel is still better than writing no novel at all. There is valiance in the effort. And you might end up becoming a great writer after all. Don't let your dreams ruin your life. 

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