Back in the rollicking 90s when Sara and I were in a band together, we would spend a lot of time in the car together with our two bandmates, Rob and Paddy, traveling from central Virginia to DC, North Carolina, and as far as Atlanta. With that much time in the car together, we had to come up with ways to entertain ourselves—especially in the days when cars had unreliable tape decks prone to overheating and radio was geographically contingent.

The four of us are all intensely verbal, and so were our car games.
20,000 questions was a favorite.* The rules were simple and absolutely wide open. The answer could be anything and the questions could be endless. I wish I could remember some of the absolutely random things we came up with—Paddy had one that somehow involved tinfoil that stumped us all until we gave up in laughing exasperation. There was an art to picking answers that were creative but weren’t completely impossible—and as I remember, we were mostly pretty good at deducing each other’s answers…eventually.
But what we got really good at was coming up with inventive questions to get at the often incorporeal and bizarre answers we each came up with in turn.
Why I am I telling y’all about 20,000 questions? Partly because I love to tell stories, but also because I am increasingly fascinated by questions and the art of asking them. Chalk some of this fascination up to my training and work as a coach in the International Coaching Federation style—but my interest predates my work as a coach by a long time.
Over the years, I’ve developed (or adopted) a bank of questions that I ask of my own writing. Now that I’m working as a developmental editor and coach for academics, I ask such questions of others’ writing. So in today’s newsletter, I offer a few of my favorites:
What’s the story?
This Hiberno-English colloquialism might feel basic, but it has the power to unlock narrative flow even in genres that aren’t “supposed” to be about stories.What does this piece of writing need to DO in the world?
This question was (probably still is!) one of my PhD advisor’s favorites, and I have adopted it with enthusiasm because it can help prevent scope/topic drift. In academic writing, it’s also useful as a prompt for the often-dreaded paragraph about why readers should care about what they’re reading.Who needs to hear this?
It can be terrifying to think about our audience, so sometimes we just try to pretend they’re not there. That’s a fine tactic for getting words down, but at some point it’s time to acknowledge and embrace our readers.What do readers need to know to understand what I’m writing about? What do they not need to know?
I want to tell everybody ALL THE STORIES RIGHT NOW AT THE SAME TIME, but apparently that’s overwhelming? jk. Of course it’s overwhelming! Introducing this question is extremely useful in paring down backstory/background information, especially in academic prose where authors generally know way more than we can include in any one piece of writing.Is it an animal, a vegetable, or a mineral?
Is this post a llama? (Only occasionally.) Does this post have a crystalline structure? (Partially.) Ok, I don’t really ask my writing this question. But I do ask myself questions about its genre and tone—fundamental questions that have to do with the nature of a piece of writing.
Do you talk to your writing? If so, what questions do you ask it? Let us know in the comments!
* Another favorite was “Jumping to Conclusions Day.” Maybe we’ll tell you about that one in some later newsletter….
NTTWC Podcast
In last month’s podcast, Tes interviews Sara about her fascinatingly winding path toward becoming a published novelist. We’ll be recording this month’s podcast soon, but until then, have a listen if you haven’t already!
What We’re Up To
Sara is working on the beginning of a dark/sexy/cozy new novel about cheating death?
Tes has had a really fulfilling week of editing, coaching, and fiddle teaching and is looking forward to studenting—the first Coaching Neurodiverse Clients class with awesome academic coach trainer Katie Linder begins this Saturday!
Schedule: January 12–January 30, 2025
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Sunday, January 12: asynchronous sprint on the Substack chat
Monday, January 13, noon ET: Zoom writing sprint (75 minutes)
Thursday, January 16, 9pm ET: Zoom writing sprint (75 minutes)
Sunday, January 19, 4:30pm ET: Zoom writing sprint (75 minutes)
Thursday, January 23, 9pm ET: Zoom writing sprint (75 minutes)
Sunday, January 26: asynchronous sprint on the Substack chat
Monday, January 27, noon ET: Zoom writing sprint (75 minutes)
Thursday, January 30, 9pm ET: Zoom writing sprint (75 minutes)
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Tes, I love the idea of talking to our writing! Give it autonomy and see where it wants to go! These are great questions! I'm knee deep in writing, currently, so your post is very timely. I love the last question (animal, mineral, or vegetable), actually. It inspired a few others for me that are silly but might push things in new directions:
1. If your book/writing were a piece of music, what genre would it be? Where might it need more dynamics, maybe a crescendo or a rest, etc.?
2. Is your writing whispering, shouting, or singing? What might happen if it shifted its tone?
3. If this section were a meal, is it nourishing, indulgent, or experimental (there's always someone on the cooking shows who is doing some crazy molecular gastronomy thing)? What flavors are missing? What texture does it have?
4. Is your book treating its audience like collaborators, students, or distant spectators? How might that relationship evolve? I love this question because it keeps the reader's experience and participation in mind.
5. What does this chapter/section fear, and what does it desire? Does that emotional undercurrent shine through? In the 90s, I wrote a lot of music and was always asking what does a section need or what is it trying to do and the same can be asked of our writing, of course.
6. If this writing were a physical space, what would it invite readers to do—linger, explore, or pass through quickly?
7. If this writing had a shadow—something it avoids confronting—what would that be? How might engaging it transform the work? I'm currently contemplating this one about a section that I'm struggling with. I think it's because I haven't done the "shadow work" yet on it.
Thanks for the brain food!! It was a great way to start the day and the new week!