Chapter 69: Cheryl Strayed on forging fearlessness and fracturing facades

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I am so delighted to close out 2020 with the magical wisdom of the one and only … Cheryl Strayed.

Cheryl is the New York Times bestselling author of Wild, the Oprah’s Book Club pick turned blockbuster film starring Reese Witherspoon, Brave Enough, a collection of raw and unflinchingly brave quotes, and Torch, her award-winning debut novel.

And then there’s my personal favorite! The Dear Sugar Column she wrote for years in The Rumpus literary magazine where she navigated the deep tissue of the human experience through raw and honest advice under the pseudonym Sugar. Since the letters were also written under pseudonym it’s an exquisite portrait of anonymous loving beating hearts of humanity connecting with no names and no faces — just riding the waves of life together. Cheryl’s bestselling book Tiny Beautiful Things is a magnificent compilation from the column that spawned the hit podcasts Dear Sugars and Sugar Calling.

How did Cheryl gain such deep perception of the human experience?

Is it through the abuse she discusses suffering as a child and her upbringing in “the boondocks” of Minnesota in a house her family built without electricity or plumbing? Was it through the sudden death of her mother Bobbi while she was in her senior year and the famed walk she took afterwards up the Pacific Crest Trail? Was it the MA in Fine Arts she got from Syracuse where she was mentored by George Saunders? Or is it simply the sum total of her incredible perception on top of the varied experiences she’s had through jobs as waitress, youth advocate, political organizer, activist, and even emergency medical technician?

All I know is Cheryl is a singular, lyrical, big-hearted voice who never shies away from the deep questions. In this conversation we discuss things like: How do we deal with grief? How do we live objectively in a subjective world? How should we think about meeting our heroes? What is the power of community and connection? How do we write with vulnerability?

And of course, what are the eminent Cheryl Strayed’s … 3 most formative books?

Let’s go!