Writers in the Storm

A blog about writing

storm moving across a field
June 29, 2018

Top 10 Success Tips From Cheryl Strayed

Top 10 List

Over the last few months, I've shared "Top 10" lists from several authors on the topics of writing and success. This month I chose Cheryl Strayed, author of WILD (one of my favorite books),  because she has so much practical wisdom to share about life. For years before WILD gained popularity, Strayed moonlighted as Rumpus advice columnist, Dear Sugar, answering questions about life and love, sex and marriage, about dysfunctional families and the importance of healthy boundaries.

Here are ten of my favorites gems from Cheryl Strayed on success, in life and in art:

1. Every book is inherently full of possibilities.

In WILD, Strayed recounts her 94 day journey on the Pacific Crest Trail where she pushed her body in an effort to heal her spirit. The trail was the thread that ran through the book and she built off that. Your book could be about war or mermaids or housewives but you will decide what goes in it, based on the lesson you want to impart or the "why" of your particular story. Be open to the possibilities.

2. "Success" is a subjective term.

As Sugar, she wrote, "You don’t have to get a job that makes others feel comfortable about what they perceive as your success. You don’t have to explain what you plan to do with your life. You don’t have to justify your education by demonstrating its financial rewards. You don’t have to maintain an impeccable credit score. Anyone who expects you to do any of those things has no sense of history or economics or science or the arts. You have to pay your own electric bill. You have to be kind. You have to give it all you’ve got. You have to find people who love you truly and love them back with the same truth. But that’s all.”

3. The world owes you nothing.

One of Cheryl's most famous quotes is, "You don’t have a right to the cards you believe you should have been dealt. You have an obligation to play the hell out of the ones you’re holding. There is no why for which cards you get. They just are. Earning a living, even in ways you find unpleasant, will give you faith in your own abilities." [Amen, sister!]

4. You can find peace in the "obliterated place."

In her Rumpus column, Dear Sugar spoke with a father who had lost his son to an impaired driver.  She called that deep well of grief "the obliterated place."

"The obliterated place is equal parts destruction and creation. The obliterated place is pitch black and bright light. It is water and parched earth. It is mud and it is manna...The real work of deep grief is making a home there. That’s now your world, where everything you used to be is simultaneously erased and omnipresent." She said, "You go on by doing the best you can, you go on by being generous, you go on by being true, you go on by offering comfort to others who can’t go on, you go on by allowing the unbearable days to pass and allowing the pleasure in other days, you go on by finding a channel for your love and another for your rage."

5. Self-pity is a dead end road.

"Nobody's going to do your life for you. You have to do it yourself, whether you're rich or poor, out of money or raking it in, the beneficiary of ridiculous fortune or terrible injustice. And you have to do it no matter what is true. No matter what is hard. No matter what unjust, sad, sucky things have befallen you. 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."

6. How to get unstuck.

So many people, writers or not, feel stuck. Like they couldn't possibly move from the place they are now to where they want to be.

Strayed says, “This is how you get unstuck... You reach. Not so you can walk away from [what or who] you loved, but so you can live the life that is yours — the one that includes the loss...but is not arrested by it. The one that eventually leads you to a place in which you not only grieve, but also feel lucky to have had the privilege of loving. That place of true healing is a fierce place. It’s a giant place. It’s a place of monstrous beauty and endless dark and glimmering light. And you have to work really, really, really effing hard to get there, but you can do it.”

The person she gave that advice to had lost a child. Most losses are less than that - loss of hope, identity, dreams. We can move beyond them to the place where we don't feel stuck.

7. Be gentle with yourself.

Strayed believes, "You will not write well from a position of shame. You are creating something out of nothing. Be gentle with yourself while you create. Only when I'm gentle with myself can I actually let go and do the work." She must forgive herself for any lapses so she can get back to doing the work.

8. Write.

The only way to be a writer is simply to write, then write some more. Keep the faith that your work is meaningful and just WRITE. If you can only write one day a week, write your heart out that one day. Write as often as you can and never give up.

9. Writing teaches you resilience.

"You can only take each day as it comes," says Strayed. "Sometimes you fail and sometimes you succeed, and every day is different. Resilience means you come back to the page to chase the dream for one more day."

10. Embrace "Motherfuckitude."

In this interview, Strayed mentions "the Art of Motherfuckitude," and explains what that sentiment means to a writer. It all began with a Dear Sugar column, where so much of her wisdom first came to light.

She told a young twenty-six year old writer, "I thought a lot of the same things about myself that you do...That I was lazy and lame. That even though I had the story in me, I didn’t have it in me to see it to fruition, to actually get it out of my body and onto the page, to write, as you say, with 'intelligence and heart and lengthiness.' But I’d finally reached a point where the prospect of not writing a book was more awful than the one of writing a book that sucked."

Strayed sees the unifying theme of any writer's life is an intersection between resilience and faith.

"The unifying theme is being a warrior and a motherfucker. It is not fragility. It’s strength. It’s nerve. And “if your Nerve, deny you –,” as Emily Dickinson wrote, “go above your Nerve.” Writing is hard for every last one of us—straight white men included. Coal mining is harder. Do you think miners stand around all day talking about how hard it is to mine for coal? They do not. They simply dig. So write... Not like a girl. Not like a boy. Write like a motherfucker."

Bonus Ten: 10 Pieces Of Timeless Advice On Love And Life From Cheryl Strayed That Can Ail Almost Any Situation


Strayed's Dear Sugar advice column was both painful and uplifting in its naked honesty. How do you bring that naked honesty to your writing? Which of these ten bits of wisdom resonates the most for you? Which ones do you struggle with?

*  *  *  *  *  *
About Jenny Hansen

By day, Jenny provides training and social media marketing for an accounting firm. By night she writes humor, memoir, women’s fiction and short stories. After 18+ years as a corporate software trainer, she’s delighted to sit down while she works.

When she’s not at her personal blog, More Cowbell, Jenny can be found on Twitter, Instagram and Facebook, or here at Writers In The Storm.

23 comments on “Top 10 Success Tips From Cheryl Strayed”

  1. Resilience is such an important aspect of being a writer. Things just don't go your way enough times that if you can't get back up and keep going, you won't make it. This year, I actually thought about having a theme song and decided on Kate Bush's "Rubberband Girl," in which she says:
    A rubberband bouncing back to life
    A rubberband bend the beat
    If I could learn to give like a rubberband
    I'd be back on my feet
    Yep, I want to be a rubberband writer. 🙂

  2. Love that, Julie. All of the above. I loved Wild, and her raw, laser focus that made it impossible to turn away from harsh truths. I strive for that in my writing, and in my life.

    1. In that video she says she spent years working on her craft before she tried to publish. She also managed to procure some of those elusive fellowships where they help support you financially as you write your book. (Can you imagine???) Its interesting to see what different roads each writer takes, isn't it?

  3. I love this article! Each and every one of us needs this advice at some point or another in our writing lives. I will share the link to this post on my blog for next Friday's 'Week in Review', which you can find at harmonykent.co.uk. From past experience I know how important both resilience and confidence are. Thanks for a lovely post 🙂

  4. Wonderful article! I especially relate to forgiving one's self for lapses then move forward, and the resilience writing helps with - every day is a new day.

    1. It has always amazed me how much harder It is for me to forgive myself than it is to forgive others. She writes a lit about forgiveness and I have soaked up every word like a starving woman. ?

  5. I love these thoughts, Jenny--and thank you for your own responses to your well-chosen top 10 from Strayed. What you chose says a lot about you, or your aspirational you--and I see wisdom, generosity, love, and tenacity.

    I'll be sharing this column.

  6. "Your book could be about war or MERMAIDS..." Yes, ma'am - got my attention in the first paragraph. LOL Thanks for these words of encouragement, Jenny. I'll especially take to heart about being gentle with myself while creating.

    1. I put the mermaids in for you, my friend. 🙂 I'm glad you liked them. And it is so (SO) hard to be gentle with oneself. But we make something wonderful out of nothing but imagination - if we aren't gentle with ourselves, those new worlds cannot be born. Think of THAT next time you try to kick your own ass!

  7. "Write like a motherfucker."

    She's so right! I think something's happened to me lately in terms of my writing, and this, I can blame it on! i just don't care anymore about the fear. Fear of success, fear of failure, fear of writing so bad that it stinks like my dog's business!

    I have to write because the opposite, living the life I dread, working a dead-end job I hate and not leaving anything with my name on it behind, well, that is the motherfucker for me!

    Thanks much Ms. Strayed, and WIS for reminding us all of this!

    Write on peeps!

    1. Lisa, I am going through the same renaissance! She expressed that the pain of not writing her novel became greater than her worry of what would come out of her. That's where I'm at, and we shall write on...like the magnificent motherfuckers we are. 🙂

  8. 9. Resilience...because coming back and doing it after a rejection or a loss or whatever gets in your way means you don't give up. fight the fight.


  9. […] Jenny Hansen just got her world rocked by Jennie Nash’s class at CreativeLive: Write Your Book – Start Strong and Get It Done. If you watch the class, you’ll see Jenny in the front row of the audience!  Currently, Jenny is hard at work on a memoir she describes as “Like WILD, but with pregnancy…and funny.” You can enjoy her silly fun at her personal blog, More Cowbell, or read her latest post here at WITS, Top 10 Success Tips from Cheryl Strayed. […]

  10. Thank you for this inspiring post! Cheryl Strayed's advice rings so true to me because she grounds her optimism for a bright future with reality about the hard work that future will require. Plus she leaves me feeling capable of both the hard work and success. I loved the post and the video.

Subscribe to WITS

Recent Posts





Copyright © 2024 Writers In The Storm - All Rights Reserved