Writer’s Block? 20+ Writing Prompts From Cheryl Strayed

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Going into the Cheryl Strayed workshop, the tally of words written on my new project was exactly: 0. And it had been that way for longer than I care to admit.

I’m not normally one to delay starting a book. In fact, if memory serves, the first section of all eight books is mine. When we were writing together, Beth and I had a deal that if I started the books, she’d end them. This is, by the way, why you should get yourself a writing partner. For the co-dependent coping.

KONICA MINOLTA DIGITAL CAMERA (image source)

Usually, staring at a blank page is not a problem for me, whereas it makes Beth feel like all good has left the world and she’s standing on the edge of nothing and if she so much as types a keystroke, Michiko Kakutani will read it and mock her like a mean middle-school girl. On the other side of the coin, I am the worst at wrapping up a novel. If it had been my job to end all of our books, they would have each concluded with a section something along the lines of: Why are you still reading this? It’s over! Can’t you see that?! What do you need from me? Should I kill all the characters off? Would that help? Yes? Fine, they’re dead. All of them. Now GO AWAY.

But for whatever reason starting this book was proving daunting. I’ve blogged about writer’s block before and I’m happy to say I have a new cure. Hang onto your dentures. It’s a revolutionary one. Ready for it?

Write something.

That day Cheryl had us do a series of 10-minute writing bursts based around prompts. When she first announced that we’d be doing this, I felt a little grumbly. I wasn’t in my writing chair! And there were 200 people in the room! And my hair hurts!

I’ve had to do these writing exercises before and often the prompts themselves are painful, very “what kind of tree would you be and why.” Usually I spend the entire 10 minutes writing some version of: I’m not a tree. Why on earth would I be a tree? This writing prompt makes no sense…

The prompt Cheryl started with was: Write about when you knew something was over. My fingers hovered over my tablet. I had something for that. In fact, I really wanted to write this story. The clock started and soon my fingers were flying, a sensation that felt even better given how long it’d been.

We did a handful of other prompts and by the end of the day, I was a believer in the power of writing prompts. I won’t use any of the short sketches I pecked out that day, but they got me back on the horse, so to speak. And they reminded the physical me of how this whole writing thing felt and the mental me that this was a thing we knew how to do.

And since then, I’ve been making slow and steady progress on my new book. The secret to writing is, and always ways, writing itself.

Hammond_typewriter (image source)

But if you need a little help getting unstuck, Cheryl was generous enough to share her writing prompts with everyone. You can find them on Albert Flynn DeSilver’s blog (he was the organizer) or I’ve pasted them below. (Oh, man. That first one is so good. Maybe I’ll write that one just for fun.)

 

Cheryl Strayed’s Writing Prompts

 

Write about a time when you’d dressed inappropriately for the occasion.

Write a few pages in which you obsess over something meaningless.

Write about something/someone being born.

Write about something you can’t deny.

Write about what you have too much of.

Write about when you knew you were in trouble.

Write about something you don’t exactly remember.

What about what you used to know how to do.

Write a long apology.

Write about a secret being revealed.

Write about all the secrets that have been kept from you.

Write about a gift that was not well received.

Write a long thank you letter.

Write about something you are certain of.

Write about having no fun at all.

Write about when you knew something was over (or had begun).

Write about someone you forgot.

Write about a question you wished you’d asked.

Write about something that was too small/too big.

Write about what you’d planned to do.

Write about something that doesn’t get better.

 

PS Can we talk about Anne Lamott one more time? I was listening to “This American Life” a few weeks ago and encountered this piece with Anne. It’s definitely worth a listen. It’s about faith, her fear of flying, and music.

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Way back in March, Holly convinced me to sign up for a one-day writing workshop with Cheryl Strayed. Actually, at the time, it took no convincing. I adore Cheryl and have read both Wild and Tiny Beautiful Things. In fact, when someone I know is going through a rough patch, I like to give them a copy of Tiny Beautiful Things. Cheryl is wise and real and kind and flawed, and I love her with that special place in my heart reserved for Wise Women. (Anne Lamott fits into this category too.)*

But as the day of the seminar approached, I was filled with dread. Why had I agreed to give up a precious Saturday during a very busy month? What if it was a complete waste of time and money? And groan, it was an hour away and it started at 9am. I seriously considered canceling. But the great motivator was there: the money was paid.

And so it was that two very pregnant women woke up at 6:30am on a Saturday and drove to Petaluma to see a New York Times bestselling memoirist and do…well, who knew? Holly and I shared our fears about what might happen at the seminar on the drive over: Would they make us read aloud? Trust falls? Picture ourselves as a tree and write about it?

Cheryl Strayed

Within minutes of being in Cheryl’s very capable hands, I was so thankful I was there. Lately, my writing has been suffering. If I so much as sit still these days, I doze off. It’s a struggle at work too–but there I have a full day of meetings to attend and people stopping by to discuss issues, so it keeps me moving. But at home, pecking away at my computer, things get awfully quiet and then the pregnancy exhaustion wins.

Also, it’s time to start the actual writing of my new project and I’ve been putting it off, fearing that dreaded blank first page. I’ve been telling myself that I’m not ready yet. Maybe I should do more research? Take more notes from scholarly texts? Perhaps I should build a detailed outline on notecards like some writers do? But these are just forms of procrastination wearing good disguises.

Cheryl was having none of it. Yes, there were 300 people in the room. You may claim she wasn’t talking directly to me, but I know the truth. She saw me out there and she knew I needed some tough love and she went for it.

Someone asked Cheryl: How do you balance motherhood and writing?

She explained that she wrote Wild when she had two children under the age of 20 months. TWO! To her thinking, you needed to find something that worked for you. She acknowledged that writing every day has never worked for her: she’s a “binge writer.” Instead she would check herself into a cheap, boring hotel near her home for two nights and write non-stop for two days, leaving only to grab food so she could keep going. Then, she’d come home to her family.

Respect? Earned.

But there was something else she said that really stuck with me. Cheryl believes that writers have a central question at the body of their work that they’re trying to answer. She said in her case it was: How do you bear the unbearable?

No matter what she writes–a memoir about hiking the Pacific Crest Trail, a novel about a troubled family, a Dear Sugar advice letter for The Rumpus–she’s always trying to answer this question because it’s the central question of her own life. Cheryl had a particularly brutal childhood and then lost her mother in her twenties. She’s had to bear the unbearble and yet she’s still here. (She suspects the answer she’s come up with is: you keep walking.)

This got me thinking about my own life and what I’m writing about again and again.  I do see a connection in my work, even from the very first scraps of writing I did in college. But I’ve never stopped and thought about what I’m always trying to talk (and walk) the reader through.

Do you know the central question at the heart of your work?

 

*One day I found this amazing video of Anne Lamott and Cheryl Strayed in conversation and my head nearly exploded with happiness. My two favorite wise women know each other! And they got together to discuss wise things!

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