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Simplify Happiness: Cheryl Strayed On Three Main Life Questions We All Struggle With

Simplify kicks off Season 4 with words of wisdom from Cheryl Strayed, the author best known for her blockbuster memoir, Wild, and advice column, Dear Sugar.
by Natallia Darozhkina | Aug 23 2018

In the first episode of Season 4, Caitlin talks with Cheryl Strayed about how tending to humanity’s toughest quandaries has become her calling, and the three central questions that keep us all up at night.

Through years of listening deeply and sensitively to others’ experiences as well as her own, Strayed has unlocked what makes a good advice-giver and friend: sincerity, listening without judging, and connection. This—paired with her straight-shooting style—is why thousands of people have trusted Sugar with their deepest secrets. In all of her work, from memoir to advice to fiction, she teaches us all to listen deeply to our own inner voices for the truth we already know.

Using simple, poetic language, she explains how to treat ourselves with respect and how to connect with those around us.

“You could write a lot of really competent sentences and say nothing, if you’re not willing to really examine the human, the soul, the spirit, and the heart.”
Cheryl Strayed

Get comfortable and tune into this episode with Cheryl Strayed to ponder how to move on after a deep loss or a heartbreak and reflect on the three major questions people struggle with throughout their lives.

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Who’s Cheryl Strayed?

Cheryl Strayed

Photo of Cheryl Strayed by Joni Kabana

Cheryl Strayed is the author of the #1 New York Times bestselling memoir Wild, the New York Times bestsellers Tiny Beautiful Things and Brave Enough, and the novel Torch. Wild was chosen by Oprah Winfrey as her first selection for Oprah’s Book Club 2.0. Strayed’s books have been translated into nearly forty languages around the world and have been adapted for both the screen and the stage.

Cheryl Strayed’s recommended reads

1. Educated: A Memoir by Tara Westover

Educated is a memoir and an autobiography of Tara Westover – the seventh child of Mormon survivalist parents. Born sometime in September, 1986 with no birth certificate issued, Westover grew on a remote mountain in Idaho. At the age of 17, she chooses to leave home and get a formal education – the decision which drives her book, and has changed her life.

Comment from Cheryl:Educated by Tara Westover is a really interesting memoir about essentially her coming of age and going from living in this rural, Idaho house with her family, and essentially being kept from modern society. She didn’t even begin her formal education until she was like 17 and went to college, and the whole world opened up before her. Really an extraordinary book about about her journey.”

2. Okay Fine Whatever by Courtenay Hameister

For most of her life, Courtenay Hameister lived in a state of near-constant dread and anxiety. But in her mid-forties, she came to realize that she must fight back against her fears and anxieties. She chose to become braver by experiencing those kinds of things she has spent her life avoiding. Thus, during a whole year she was doing things that scared her: attended a fellatio class, got high during a workday, had a session with a professional cuddler, went on twenty-eight first dates, and possibly actually met someone who appreciates her for who she is.

Comment from Cheryl: “…It’s about her struggles with anxiety and essentially body image and, you know, all of the many many struggles many of us go through. And then she invented a few of her own as well. And it’s about her sort of year or so of trying to push herself out of her comfort zone in order to heal some of her wounds. Really really good book, really funny and also poignant.”

Extra credit reading

If you would like to learn more about how to better communicate your needs and listen to your inner voice, check out this book list composed by Ben and Caitlin!

This book introduces the principles of Nonviolent Communication (NVC) as a compassionate way of being with ourselves and others. Through simple techniques, you can learn how to consciously change your language and thinking to forge better quality relationships with others.

Walden (1854) is the result of the two years Henry David Thoreau spent in the woods on the north shore of Walden Pond, a lake in Massachusetts. It is both a practical and philosophical account of how he sustained himself through farming and by building his own house, and what he learned about human nature by living a simpler life. Although it was a deeply personal experience, Thoreau’s approach to society teaches us how we, too, can approach the modern world.

On the Road by Jack Kerouac

On the Road tells a story about cross-country journeys of two friends, Sal Paradise and Dean Moriarty – the fictional alter-egos of Jack Kerouac and the Beat writer Neal Cassady. It is the defining work of the Beat Generation, a movement of young people in the 1950s and early 1960s who rejected conventional society, valuing free self-expression and favouring modern jazz.

The Art of Asking is Amanda Palmer’s personal account of how she developed her philosophy of asking, sharing and connecting. This book gives you an in-depth understanding of how to accept help, reciprocate the generosity of others and build a tight-knit, family-like fan base to support you in whatever you do.

What’s Simplify?

Simplify is a podcast for anybody who’s taken a close look at their habits, their happiness, their relationships, or their health and thought “There’s got to be a better way to do this.” We talk to bestselling writers, productivity wizards, sex geniuses, and happiness experts to find it for you.

Simplify is made with love by Blinkist. Click here to try Blinkist free for 14 days with the voucher code: sugar

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Talk to us!

We want to hear from you! Reach us at [email protected].

If you want to say hi to Ben and Caitlin in the meantime, you can find them on Twitter: @bsto and @CaitlinSchiller.

Who made this?

Your hosts are Caitlin Schiller and Ben Schuman-Stoler.

Research and production assistance by Nat Darozhkina, sound and editing by Ben Jackson.

Thanks to Nico Guiang for our awesome intro and outro music. Listen more on Soundcloud or check him out on Facebook.

Got links?

Cheryl Strayed’s website:
Dear Sugar Advice Column:
Dear Sugars Podcast:

Read the transcript here!

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