I hate outlining...but doing it backwards works

If I have to outline, *reverse* outlining is the method that works for me.

Re-sequenced claims for the overview section of my next book proposal (©B.G. Merkle, 2026)

Dear Troublemakers,

I’m once again away, co-leading the annual proposal writing retreat I co-founded several years ago. As I wrote last spring [1], the essence of the retreat is “any kind of proposal that aims to persuade someone to support your work.”

My co-facilitator and I always bring our own projects to work on, alongside the participants. Last year, I was working on a cover letter and manuscript package to submit my poetry collection to various publishers. [2] This year, I’m drafting a proposal for a book about the emotional side of scientific writing. On Tuesday, I opened up a document where I’d been organizing my ideas and discovered I’d last touched the idea directly in April 2025. In that year-old draft, I found many good ideas about why this book is needed and who it can help.

But, as I re-read and started revising that existing text, I had the feeling that much of my rationale for the book was scattered about in the wrong various parts of the proposal doc. In particular, as I was refining my comps [3] section, I watched myself type out justifications/differentiation claims even as I was aware these arguments should probably appear much earlier in the pitch.

I left that dilemma to future me, which turned out to be Wednesday me. I’m a very visual thinker. Working on a laptop, not my usual double-screen set-up, feels like losing half my brain: I can’t readily see what I have alongside what I am turning it into. So, yesterday morning I resorted to a tool that I discuss in some detail in my current book, Teaching and Mentoring Writers in the Sciences: reverse outlining. [4]

Reverse outlining is yet another awesome tool from the Writing Studies/Rhet Comp disciplines that we should be using habitually in the sciences ( but spoiler: we largely aren’t because we mostly don’t know about it. And even when we, ahem, me, do, we don’t always employ it).

In brief, reverse outlining is the practice of closely reading your own work [5] to identify the content, structure, and flow of the document. This method stands in contrast to typical outlining, which is aspirational or directive and reflects what you intend to write—not what you actually have.

At its simplest, a reverse outline can show you where you’ve put your ideas in a draft text, and whether you have content or flow gaps. In a more involved sense, reverse outlining can emerge as a revision and rethinking tool. And that’s what I tapped it for yesterday.

I specifically needed to corral the justifications I was presenting for why this book was needed. So, I went through my whole draft proposal and highlighted each sentence/phrase that conveyed these claims. As I went, I wrote each claim on an index card, numbering them in order of where I found them in my draft text.

It took me several hours to do this, because I also kept thinking of more justifications and drafting them into the text. Then, I just couldn’t resist re-arranging a few parts directly in the doc, since I knew they should be in a different order. But neither of these interventions fully resolved the issue of my justifications being scattershot throughout the whole doc.

So, I then saved myself a lot of computer angst. Instead of trying to see the whole doc and move all those pieces around on one tiny screen, I laid out all my index cards in the order they were numbered. And then I started re-ordering them, building a coherent flow that would carry a reader into and through my suite of justifications.

My sequence wound up looking like this:

The probable sequence of ideas in my book proposal’s first section (©B.G. Merkle, 2026)

I felt pretty confident about the sequencing, once I had physical objects to put in a coherent, compelling order. While it took me a couple hours to highlight all my claims and write them on index cards, it took me less than 10 minutes to re-order them. Ideas/claims will now run in this order: 2, 3, 1, 4, 18, 10, 11, 5, 7, 9, 6, 16, 8, 12, 17, 13, 14. And, I’ve marked another card with a note about whether last two (13, 14) should actually precede 12 and 17. Revising the whole overview section in 10 minutes was an efficiency contingent upon making the components of the draft tangible. It also relied upon me relinquishing any need for the current draft to dictate the next draft’s content or structure. Considering the state of my emotions and cognitive overload right now, I am confident that it would have taken me hours or days to arrive at this sequence if I had done it only on the computer/in the draft document.

Similarly, I have learned over decades of writing professionally that I do not usually know what I want to say before I start writing. So, while I can create an outline (and occasionally do if forced to), I am consistently certain my outlines are incomplete before I even start drafting. Instead, I’ve found my workflow is more effective (albeit questionably efficient) when I hammer away at the keys a while, then start revising for both content gaps and more compelling flow. What I’ve just re-learned is that I can make that revision far more efficient by physically getting my hands on it.

How about you?

Do you use outlines for your writing? Have you tried reverse outlining? Do you ever go rogue analog and render your revising tangible with good ol’ index cards, sticky notes, or the like? Why or why not, and where have those writing habits gotten you?

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NOTES

[1] Even if you’re not interested in this specific retreat, the post is primarily a word-nerd reflection on the many meanings of retreat and how they can play out in our lives. Lemme know what you think of it!

[2] Spoiler—no takers yet, but I’ll keep trying.

[3] “Comps” are the comparison or competitor books that you are expected to point to, when writing an academic book proposal or similar, to indicate you’re aware of how your book idea fits in the field—and why your book is still necessary/does something the others don’t/takes an idea further, etc. For more context about comps in academic/ac-adjacent proposals see Laura Portwood-Stacer’s The Book Proposal Book. For info about comps for creative nonfiction/memoir and fiction proposals, see Courtney Maum’s Before and After the Book Deal. Both Laura and Courtney also have blogs/newsletters with great insights on the subject.

[4] Reverse outlines are mentioned 10+ times in my book, starting in chapter 3. In particular, we define reverse outlining and suggest several ways to assign, facilitate, and or offer it as a tool to developing writers. See the index of the book to find those spots. The crucial idea, though, is that reverse outlining is not just “training wheels.” It is a valuable tool for experienced writers—that is why we teach it to developing writers.

[5] You can also use it to analyze a model text (e.g., an example of a published paper or successful grant proposal) and identify the necessary sections and key rhetorical moves made in that text. If you’re going to do that, my collaborator Rick Fisher’s “Reading Like a Writer” worksheet (perhaps with modifications you make to recalibrate the prompts to the type of text you’re analyzing) can be a great tool for guiding how you “chunk up” the text into a reverse outline.