What I Learned About Life and Writing Onstage with Cheryl Strayed

Cheryl Strayed's Brave Enough, A Conversation with Theo Pauline

Photo: Jason Tang

A few weeks ago I did an onstage conversation with Cheryl Strayed here in Seattle about her new book, Brave Enough, a collection of quotes that yield up her trademark no-nonsense wisdom. The entire experience was a Dear Sugar Boot Camp of learning that began the moment Cheryl asked me to do the event (Why would I want to do such a scary thing and yet how could I not want to?) and continued all the way through my preparation (Reading Brave Enough several times in a row alters the molecular structure of your cowardice) and throughout our 1.5 hours onstage.

Here are two of the nuggets of Strayed wisdom I gained from the experience:

Nugget 1: How to Not Let Fear Ruin What Actually Could Be Fun and Joyful

brave enoughAgreeing to do the event meant that for the first time in my life I would be onstage in front of 800 people. Very quickly I decided that I didn’t want this nice opportunity to be a source of dread and anxiety. I  thought about the onstage conversations I’d enjoyed listening to the most, which were invariably the ones in which the interviewer was at ease and the conversation had the intimate quality of friends talking. Even though most of us find public speaking daunting, no one wants to watch the spectacle of anxiety. As audience members, we want to be transported by bold confidence. So my task was to access that confidence pronto. As I was wondering how I might do that, I was reading the galley of Brave Enough and came across this quote from Wild:

Fear, to a great extent, is born of a story we tell ourselves, and so I chose to tell myself a different story from the one women are told. I decided I was safe. I was strong. I was brave. That nothing could vanquish me. Insisting on this story was a form of mind control, but for the most part it worked. Every time I felt something horrible cohering in my imagination, I pushed it away. I simply did not let myself become afraid. Fear begets fear. Power begets power. I willed myself to beget power. And it wasn’t long before I actually wasn’t afraid.

What better way to prepare for the event than to apply the wisdom Cheryl shares in the very book we’d be discussing?  I began to tell myself that being afraid wasn’t an option, and I then remembered how during the 2nd episode of Dear Sugar Radio Cheryl had again talked about laying down the law with herself and ruling out the possibility of negative thinking:

“Right before [the movie] Wild premiered… I went into the bathroom and looked at myself in the mirror and said, ‘You are not allowed to think anything negative about your body, your weight, or your looks anymore. If you think those things, push them out of my mind.’”

As I read deeper into Brave Enough, I began to realize that this Just Say No to Bullshit Thinking is actually a crucial refrain throughout Cheryl’s writing, an essential tenet of Sugarism.

I saw it here: “You know what I do when I feel jealous? I tell myself not to feel jealous. I shut down the Why not me? voice and replace it with one that says Don’t be silly instead. It really is that easy. You actually stop being an awful jealous person by stopping being an awful jealous person.”

And here it was again: “Self-pity is a dead-end road. You make the choice to drive down it. It’s up to you to decide to stay parked there or to turn around and drive out.”

And so–fortified by these just-don’t-go-there quotes–I continued to remind myself that nervousness wasn’t an option whenever anxiety about the event started to bubble up. I also started to imagine how I wanted to feel when I was onstage. I wanted to have fun! Sure,  I wanted the audience to enjoy themselves, but I also wanted the event to actually be enjoyable for me. I felt driven to create that enjoyment for myself because there have been many supposedly fun and exciting things throughout my career that I didn’t enjoy because I was anxious. This enjoyment that I would feel onstage would be my chance to make up for all the needless worry I’d put myself through in the past.

cheryl theo besties

In the green room with Cheryl Strayed, my besties, and my younger daughter.

Did all this Brave Enough preparation work? It did. I felt a brief flash of terror as we stood behind the stage’s velvet curtain listening to our introductions, and then I said to myself, “This is the fun night that you’ve been preparing for! You got this!” And then the stage manager said, “Okay, go!” and I did.

Nugget 2: Cheryl Strayed’s Two Questions for Writers Could Save You Years of Wandering Lost in the Wilderness.

Photo: Jason Tang

Photo: Jason Tang

It seems like there was nothing we didn’t talk about during the next hour and a half. We ran the gamut from feminism, Gloria Steinem, Oprah Winfrey, grief, fear, and memoir to the female orgasm (yep!). But one of the most memorable and nugget-worthy moments of the evening was when Cheryl talked about the two questions she poses to her writing students.

“The first question I have them answer is ‘What’s the question at the core of your work?'” she said. Then she shared that hers was “How can I live without my mother?” She said that after her students form this first question, she asks them to come up with a second question–a universal one that asks “What question are you trying to answer for others?” Cheryl said that the universal question for her work has been “How do we go on when we’ve lost the essential thing?” The second question, she explained, is how the work becomes not just about the writer but about everyone as “we’ve all– at some point in our lives–lost the essential thing.”

These two questions are the gold I’ve carried away from that evening. I’ve been sharing them with all my writing classes and asking my students to formulate both an individual question and a universal one. When they go around the room and share their two questions, I think about how lucky I was to get to do this event with Cheryl and how the best type of wisdom is the kind you can use right away.

You can listen to the recording of the entire event here. If you want to hear Cheryl talking about the two questions for writers, start at minute 57:00.

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