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7 Tips for Writing and Life from Author Cheryl Strayed

cherylbyjoni-edit-680If you’ve read the book Wild: From Lost to Found on the Pacific Crest Trail or seen the movie, you know that words from Cheryl Strayed have a way of evolving into a deep, inspirational lift while stemming from dark, tragic life experience.

Author George Sanders describes Strayed’s writing best:

“Big-hearted, keen-eyed, lyrical, precise…Cheryl Strayed reminds us in every line that if defeat and despair are part of human experience, so are kindness, patience, and transcendence.”

That is the best-selling author and person, Cheryl Strayed, boiled down to one sentence.

I had the chance to hear Strayed speak at Iowa State University recently, and I was amazed by her prolific voice. She speaks the same way that she writes–ruthlessly honest and vulnerable, offering an abundance of beauty and enriching messages by stringing together a few small words.

I’m guessing I wasn’t the only writer in the audience who kept thinking, that is the kind of writer I want to be. 

Takeaways from Cheryl Strayed on Life and Writing

I filled up several pieces of notebook paper with one awesome quote after another, and listed below are some of my favorite takeaways from Strayed. The first four points are geared toward writers, but for those of you who are looking for a little shift of perspective toward life in general, the last three are for you.

Find the metaphor. Strayed recalled a rough time of her life with the visual of her digging out snow with a shovel, leading to how she’d metaphorically dig herself out of her grief. She said meaningful messages often present themselves in physical realities of moments.

“Often the metaphor is right there in your hands.”

I love this as both a general practice for looking deeper to see the meaning of a situation, but also for writers. Opening our eyes, looking around and seeing the metaphor is a great way to get a story idea or find the meaning in a story.

Write to connect, not to brag. Strayed didn’t write about her journey hiking the Pacific Crest Trail (Wild) until several years after the fact, when she could finally wrap her head around her experience. It took some time for her to see how the things she learned could help other people.

“I didn’t want to write about it just to tell people what I did,” she said. “I waited until I had something to say about it.”

We’re often eager to write about every exciting moment in our lives as they happen, but I know I’m guilty of coming back much later, reading my work and thinking man, I would write that differently now.

Our views on our experiences, especially those that impact us the most, change over time. Often, the lessons learned take greater shape in our perception after some years have passed.

Aim to seek the answer. This one was an eye-opener to me as a writer. Whenever I start writing a new story, I think of the message I want to convey. I think of what I want the reader to get out of the story.

Strayed says writers don’t provide the answers, but they provide a way of seeking the answers. Many of her readers gained different messages from Wild.

Words affect every individual differently, so they should provide a way for readers to seek their answer. Because honestly, how can we portray the same unified message to an audience with diversified experiences and thinking patterns?

Enforce disciplined writing time over a schedule. Strayed says she doesn’t need to write every day to finish a project or feel connected to her work. Scheduled daily writing time doesn’t work for her lifestyle. When she does carve out time for her writing, she makes sure that time is focused and disciplined.

This is a good take on a writing practice that I don’t hear too often. We can spend time writing every day and not get anywhere if we’re not focused on it. Strayed implies that a disciplined and purposeful session is more important than frequency.

Some lessons have to be taught more than once. It’s easy to be hard on ourselves when we make the same mistakes more than once, but some lessons have to be learned over and over. It takes repeated failure for some things to stick.

Meaning, have compassion for yourself. Give yourself some grace and know that even if you messed up something you think you should know, you’re still learning from it.

When you pretend you’re not afraid, you get to do things in life. 

“It’s not that you’re not afraid, but that you don’t let fear hold you back.”

I love this. Think of what things you haven’t done because you were too afraid–too scared of failing, scared of change, scared to shake things up in your life. But like Strayed said, you get to do so much more when you pretend you’re not afraid. It’s the whole “fake it til you make it” mentality.

There is no moving past it. It’s learning how to carry the weight the tragedy brings. Strayed’s memoir Wild is strongly based on her grief of her mother’s death. At the age of 45, her mother died of cancer only a short time after being diagnosed.

We all face grief in our lives at some point. Strayed learned she would never get over her mother’s death, but instead shifted her mindset to, how do I carry this? She learned to be grateful for the weight of her grief, because that weight was a gift of love rather than a burden.

Whether you’re a writer or not, I hope you can take away something meaningful for your life from author Cheryl Strayed. For more of her rich insights, check out Tiny Beautiful Things: Advice on Love and Life from Dear SugarTiny Beautiful Things, an exceptional book full of advice and life lessons.

Are you a fan of Cheryl Strayed’s work? What is your favorite book of hers or a lesson you learned from her writing? Leave a comment below!

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