Does Outlining Crush Writer’s Block?

Does Outlining Crush Writer’s Block?

I recently began working with a woman who was suffering from a crippling case of writer’s block.

A semi-retired addictions counselor, she (I’ll call her Jan) had been trying to write a memoir about her approach to treating addiction as a family illness. Speaking with her about her project, I could hear her passion. Jan had come from an addictive household herself, a household headed by an alcoholic father, and had later recreated that household when she married an alcoholic.

After eventually leaving him and remarrying, Jan returned to school late in life to earn her Master’s Degree and begin working in the field of addiction counseling. In our conversation, she said she had discovered a new way of helping clients see that the illness affected the whole family, not just the one abusing an addictive substance. She wanted to reach more people, to help more people, with her book.

But she was stuck.


What Does This Have to do with Outlining?

Before coming to me, Jan had been working with another writing coach. When Jan got stuck, the coach suggested she create a table of contents for the book—an outline. Jan created one, a very detailed one. She and the coach had discussed the outline itself: what to cut, what to possibly add, how to reorganize the topics.

But Jan was still stuck.

I get the image of mice running madly around in a closed box, bumping into each other, looking for the door to freedom but not finding it.

Apparently, Jan felt the same way. She was frustrated and teetering on the edge of despair about the possibility of ever putting into words the thoughts slamming around in her head.


You Have to be Messy before You Can be Neat.

Think back to when you were forced to write outlines in grade school or high school. You hated them, right? Do you remember why?

Outlines help you to organize your writing, to get a sense of what comes first, second, third. When I taught college writing, I forbade students (just kidding; it was just a strong suggestion) from outlining until after they’d written their first draft.


Because you have to figure out what you mean first, a very messy process of discovery.

Being forced to organize material you haven’t created yet can create a whole lot of frustration that can lead to (or exacerbate) a mammoth case of writer’s block.


Change the Approach: Ask Questions.

You can ask yourself all kinds of questions to get your hands moving across the keyboard or notebook again.

With Jan, I began with “Who is your audience? What do they know, believe, and feel about the topic?” I asked her to dig deep, but she stayed on the surface, so my next question was:

“You say you used to be one of them, right? What did you know, believe, and feel about the topic? Why do you want to write to them? What are you exploring in your own life?”

That series of questions set her free. She wrote pages of summary peppered with character sketches, a wealth of material. She will continue in that vein and then go back and expand each section: including more detail, creating scenes, honing dialog. And at some point, she will need to organize it.

All that is in the future. For now, Jan is happily writing, the outline tossed in the trash.


What questions can you ask about your writing that will set you free?


Note: Jan is writing a memoir, but the process of discovery holds for all kinds of writing, except straight reporting.



Pam Sourelis writes short stories and personal essays. She assists other writers as a developmental editor, writing instructor, and writing coach/mentor.; also on Facebook


2 Replies to “Does Outlining Crush Writer’s Block?”

  1. I just read this blog about myself. I am still stuck. I do believe this time away has been productive in ways though. I still have the passion for the project, I’m determined to learn how to write, and I’ve learned things about myself.

    I like your new website. I think it is more thorough or I’ve just learned enough to better understand it. I wondered if the Introduction to Memoir would be for me?

    1. Hi Kathleen. I don’t know when you posted this comment. If you’re still feeling stuck, are you interested in a 30-minute chat about what’s going on? There’s no charge, no obligation. Contact me through the contact link on any page of this site. (Sorry, I can’t link it here in the comments.) I look forward to speaking with you.

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