Recently, I converted all of my (very old) academic writing from outdated document formats (WordStar and Microsoft Word 6) to more future-proof formats: either Markdown or OpenDocument format (.odt). While I did not re-read every essay I ever wrote for school during this process, I did notice something in my files that surprised me: From my junior year of high school to my final semester of grad school, I created outlines—full sentence outlines¹—for all of my papers that were over a few pages in length. I had forgotten that I used that type of outline for more than two important projects in my academic career: my first English thesis project and my last.

My first English thesis project, wherein I learned about the sentence outline

I was first taught (i.e., forced to use) a sentence outline in high school. It was a requirement of my grade 10 English thesis project, which was a 10-page research and literary criticism paper. At the time, I understood how to create high-level outlines pretty well, but could not understand why I would create an outline that contained full sentences of the essay I was trying to write. I figured that if I could write a sentence outline for an essay, I could just as easily (or more easily) write the essay itself. In grade 10, that is precisely what I did: I wrote the essay and then split apart every paragraph and every sentence into a hierarchical outline. In doing so, I learned almost nothing.

My last English thesis project, wherein I mastered the sentence outline

For my final English thesis project, my senior honors thesis in English at Brandeis University, I resorted to a sentence outline to solve my writer’s block. It was a year-long, independent study project, and my thesis advisor—who mostly told me that despite my anxiety I was doing fine—was not terribly helpful or available. Understandably, I lacked direction. I had no idea how to write a big, scary, and academically significant 80-100 page essay. When I sat down to write, I would either produce a jumbled mess of thoughts and quotations that did not fit together, or I would compose a coherent paragraph that I could not connect to anything else I wrote. As my senior year went by, I felt as if I was falling further and further behind my brilliant, thesis-writing peers. Counterintuitively (or understandably, depending on how you look at it), this feeling of dread led me to procrastinate instead of write.

In the early spring, I realized that if I created an outline, I could work on my big, scary thesis essay without actually writing it. To that end, I split the work that had been going nowhere into two Word documents: (1) a simple, high-level outline that consisted of just a few headings at the start; and (2) an unorganized junk drawer of ideas and quotations from my source material. Outlining quickly became a productive form of procrastination for me. Instead of writing my essay, I would pluck out ideas from my junk-drawer document and drop them into the outline. From there, I would change these ideas, move them around, flesh them out, add to them, or delete them, all without committing to their precise wording or location. Because these ideas were all sentences or block quotes, my outline necessarily became a sentence outline.

Using keyboard shortcuts I no longer remember, I collapsed sections and paragraphs of my thesis outline and moved them up and down to organize my ideas, and I shifted individual sentences up and down to make my arguments clearer and easier to understand. Because I was avoiding the writing phase of my project, I avoided gluing my sentences together with logical-, narrative-, or stylistic flow until I felt sure they were in the right place in the document and in the right order in their paragraph. Doing so took some time to get used to, but granted me a feeling of tremendous freedom as I worked out the essay’s high-level structure and the fleshed out the arguments I was advancing within it.

I didn’t realize until I was finalizing my thesis—when my outline was a 100-page outline full of section headings, topic sentences, and body sentences organized into paragraph-level nodes—that I was doing exactly what I was supposed to do. I had organized my research and my findings in a format that was incredibly flexible, and I was constantly revising it and shaping it into something coherent. By accident, I had finally learned why a sentence outline is useful: It explodes an essay into individual thoughts that are physically separate² and logically atomic³. Doing so makes it easier to evaluate each one independently and—with a good word processor—to quickly group, ungroup, reorder, and move them into place.

In the end, I never wrote my thesis paper. Instead, over the course of a few months, I wrote a sentence outline. I converted it to a manuscript only a day or two before I turned in the final draft. My only edits to it, in manuscript form, were related to applying Word styles to the various paragraphs and adding a title page. The final draft must have been pretty good because it was awarded the Doris Brewer Cohen Award for best senior honors undergraduate thesis in the humanities at Brandeis University.

In grad school and beyond

I went to business school after college, and did not have to write nearly as many long papers to earn my M.B.A. as I did to earn my undergraduate English degree. Despite the small number of major papers I wrote, and despite not remembering the writing process I followed for them, I discovered that I wrote sentence outlines for each one.

After grad school, almost all of my long-form writing has been technical writing for work. While I do not have any old drafts lying around, I recall using outlines extensively to plan and structure my work, but I never again used sentence outlines to draft and perfect it. One reason for that may be that I used different software to write with: mostly plaintext editors, rarely Word (not until I had a first draft nearly completed), and never a dedicated outliner like OmniOutliner. Another reason is that much of my technical writing had to fit into pre-existing document templates that already consisted of many short sections laid out in a specific, required order.

After discovering my longer-than-remembered history of using sentence outlines, and reminiscing about the senior honors thesis project on which I mastered the use of them, I now wonder if I should go back to using them for my larger writing projects.