The Most Powerful Writing Prompt I Ever Gave
The prompt broke participants in my in-person writing workshop wide open.
It’s the second night of my expressive writing workshop. Everyone’s settled with their tea and pastry. Our space, a historic building born out of the women’s suffrage movement, is dim and quiet.
We’ve debriefed. Talked about how writing at home was challenging for some, easy for others. We discussed procrastination and the angst that arose for some of us as we chided ourselves: “OK, just do the writing thing already.”
There is so much resistance from the writers, many of whom tell me, “I’m not really a writer.”
“Can you put words on paper or screens? Do you do that regularly when you send emails or post on social media?” I ask.
Everyone nods.
“Then you’re a writer. Nobody asked whether you’re a career writer or even a talented writer. But can you write? Of course. That’s why you’re here.”
I feel like I’m butting my head against a brick wall. My participants paid to come to a writing workshop, but they lack the motivation to actually do the writing. And it’s my job to encourage them.
I’d told them about the science behind expressive writing, and how it actually helps ordinary people—not people who call themselves writers, but people who know how to form words and sentences in writing—process and heal from traumatic events.
They don’t seem convinced.
I realize that I could talk about the benefits of expressive writing all night long, but my group of would-be writers won’t take those benefits seriously until they experience them firsthand. The benefits of expressive writing haven’t clicked for them just yet. I need a powerful, universal prompt to engage them.
So, I cue up some ambient music. I invite the writers to ground themselves by noticing their breathing for a minute or so.
Then I issue the prompt that breaks them all wide open. A prompt I’ll share with you in just a moment.
Throughout our timed 20 minutes of writing, I watch from a distance as pens scribble furiously on notepads. Every one of my writers is bent over their paper, not looking up, writing in a steady stream that flows from somewhere deep.
When the 20 minutes ends and everyone puts their pens down, I look around at everyone’s faces. Some rise from their pages as if rising from a trance. Others draw their shoulders up to their ears and glanced around anxiously. I know they’ve each found a surprising well of truth within themselves.
“I’ll never ask you to share your writing if you’re not comfortable,” I say, “But if anyone does want to share a few paragraphs, we’re all here to listen without judgment.”
I glanced around. A few people shake their heads. What they’ve written is too personal, too raw, for them to expose.
Then, two friends of mine (a married couple who’d joined my workshop more to support me than anything) offer to read. Olivia [names changed] reads first, and what pours out leaves us all stunned. It’s poetic, vulnerable, beautiful, terrifying, and we all seem to relate. Then Joel reads his writing, this man who seemed least likely to participate in a writing workshop. And again, it is raw and devastatingly real.
I’ve never seen such a visceral response to a simple writing prompt, one that I dreamed up on the fly to spark a response.
Want to give it a try?
The Writing Prompt that Broke Through
Before I share the prompt, take a moment to prepare.
Putting pen to paper is best if you can manage it, but writing on your computer or device works, too. Set a timer on your phone for 20 minutes or so. The timer helps create urgency, pushing you to “write hard and clear about what hurts.” (That’s advice from Hemingway, by the way.)
Center yourself with some deep breathing. (There’s absolutely no way to do this wrong!) Tell yourself that you have everything you need to write honestly and openly. Remind yourself that you will not censor yourself as you write. You won’t stop to cross out or fix errors.
Know that if the words don’t flow, it’s OK to just write a simple phrase over and over, like “I don’t know what to say” or “I’m thinking, I’m thinking…”
And now, here’s the prompt:
What is a mask you wear that no longer serves you?
Write fast. Write true.
If something hurts or scares you, tug that thread. There’s light at the end.
This is a sample of the writing prompts my paid subscribers get every Friday. You’ll also get encouragement, advice, and a growing, supportive community of people writing to discover their own truths and, in many cases, share them with the world. Because sharing your writing leads you to one beautiful truth—whatever you’ve experienced, however you feel, you are not alone.



