While it might be a sin in some literary circles to confess, I’ve never written an outline for a single article or story that I’ve published. As early as middle school, I’d sooner get a zero on my assignment than commit to a task I considered so mundane. I resisted that outlining advice well before I learned I love to write. Before my affinity for words had entered into even its most rudimentary stages, I preferred writing more rather than less if it meant I could avoid paring down my thoughts to something so stiff and lifeless.
No matter how many teachers and professors told me I’d be served best by arranging each piece into sections before beginning, the directive never clicked. I was told I should frame each paper as introductions, theses, and body paragraphs — each assigned a separate, designated purpose. I was told the bow to tie each essay together should be neat and tidy conclusions.
With structure, the task of writing 1,000 words wouldn’t feel quite so daunting, our instructors repeatedly preached. For some students, I trust that would have been the case. For those who find themselves paralyzed by all of the forms a blank page can take, structure can provide a foothold rather than a cage. But depending on the person, such rigid mandates might leave someone believing writing is something that it isn’t. That, like math, there are correct answers and incorrect ones. That there are rules so immutable they can never be defied.
For those who turn to outlines because it’s difficult to organize their thoughts, it’s often lost on them that it’s supposed to be. We shouldn’t expect the opening stages of any creative or intellectual pursuit to be frictionless. But once we outgrow the training wheels of our first bike, we’re suddenly less restricted in our movements.
Writing is a fundamental exercise in thinking and our minds are so chaotic that they’re difficult to corral. But the practice of sitting with our thoughts long enough for them to meaningfully congeal is much of what this creative endeavor is about.
I couldn’t put words to why my teachers’ prescribed formula for approaching this art felt so unnatural. But always, when I broached a new essay or writing assignment of any sort, I was happiest just launching into my ideas.
Even classes that didn’t call for verbosity in the least I greeted as opportunities to hone my craft. My health teacher told me she’d never read the word “disinter” before reading my essay on Super Size Me. She admitted that she was forced to refer to a dictionary by the time she’d reached my third paragraph. I was awarded 100% on the should-have-been-throwaway assignment.
My AP U.S. History teacher rarely gave me less than a B for my research papers, but would jeeringly remind me, “You know, you really don’t need to treat each of these as an English exercise….” Mr. Lancer was astute enough to notice that citing my sources invariably took a backseat to crafting unnecessarily polished sentences on Andrew Jackson. My love for language was the driving force behind my work, and history never interested me much back then.
Mr. Lancer’s brother and sister-in-law were English instructors at the same school, and I reasoned since he shared their last name, he probably had a few kernels of Lancer writing wisdom to impart as well. (Despite the other two Lancers’ religious insistence on outlines — and unflappable belief that linking verbs ought to be avoided at all costs — their classes were the ones that really began to foment my passion for the subject.) So I was determined to pull that same linguistic value from Mr. Lancer’s class — despite its stubborn status as a history course. Whether the assignment was on the Revolutionary War, slavery, or the Great Depression, my eyes lit up as I got lost in each new essay and research assignment.
This lengthy opening tangent feels especially appropriate because it perfectly conveys both why I began working on this piece — and why I hate outlining. Initially, my inspiration behind this screed was the concern that I’d left something integral out of the previous article I published, and wanting to explain why that happened. I wanted to bring people inside my mind and walk them through the way that ideas snowball, drift course, and divide.
Oftentimes, a narrative will start one way and turn another. Sometimes a brief parenthetical side note will want to evolve into an entire diatribe or dissertation. Other times, as a story nears completion, I’ll realize I’m simply trying to cram too many disparate ideas together, and that each would be better off evolving into its own article. Ideas need adequate room to breathe and develop. And like cells multiplying, one column suddenly becomes two.
Despite the sheer number of times that my writings have turned into something different than I initially envisioned, there’s no other way I’d desire my creative process to unfold.
In this most recent case, the article “We Don’t Know How to Process Travel Anymore” was previously almost double its current length. In short, it’s about the way that modern travel has altered our relationship with the world. Instead of simply examining the cultural vertigo of going to sleep in one continent and waking up in another, that unabridged draft dove more into the way that contemporary travel is something so grand that it calls for words we don’t yet have. We not only struggle to adjust mentally after such geographic shifts, but we lack the vocabulary to even truly make sense of them. I included a long-winded analogy about the amorphous nature of psychedelic experiences. But as the piece stretched beyond the 10-minute marker, it started to feel too loose and incohesive for each of the distinct ideas to be housed under the same roof.
I made the decision to simply split the draft into two separate ones. And I decided that this new one would open with a brief anecdote about the writing process and then transition into my broader observation. But again, soon after I began typing, it became clear that I had more to say about my disaffection for outlines than I assumed, and that, once again, my thoughts about the wordless nature of travel would best be shelved for later when I could unpack them more thoroughly and without the added fog of an overly long anecdote.
Were I to outline my pieces beforehand, it’s likely that I wouldn’t run into such hurdles as often. But it’s these specific hurdles that are one of my very favorite parts of running along this track. I love how writing prose, at its least structured, gives me an opportunity to sit with my ideas in a more organic setting and more meaningfully grapple with the ways they connect. In what order does it make most sense to present my thoughts?
Very often, there’s such a fluidity to the mental process that when we write down our reflections on a subject in the order that they arrive, they present more humanly to others than if we’d constructed an outline. Being at the mercy of my internal dialogue as I write — rather than referring to a few bullet points about what each of my sections are supposed to contain — results in something that feels more lucid, relatable, and conversational. Less mechanical and more reminiscent of the way that our minds actually work.
Considering where an insight is leading, and how to get there without any jarring “additionally,” or “In this other example…” signposting, grants me an opportunity for deeper and more deliberate thinking. Such speed bumps detract from a train of thought’s pacing. Worse, they can derail those readers who crave continuity and logical progression.
It’s for this reason that I’ve held an enduring distaste for subheadings. While in occasional pieces they’re called into action, most often when I see them employed in prose they’re being used as shortcuts. When people don’t know precisely how one idea or event bleeds into the next, subheadings negate the need for such understandings. Vaulting over those natural bridges between notions can leave a story feeling at once jumpy and dispassionate. The logical leaps are as convenient in the moment as they are detrimental in the long term. They sidestep the intellectual legwork that enables a narrative to come together naturally.
As an editor, very often when I review a draft about a breakup, I’ll find that it’s divided into sections such as, “How We Met,” “Where It Went Wrong,” and “Moving On.” Or a travel essay might be carved into infantilizing chunks with the subheadings, “Arrival,” “Exploration,” and “Reflections.” In each case, they not only disrupt readers’ momentum, but give them an unsolicited preview of what’s coming next instead of allowing them to follow along as events unfold on their own.
When constructing new articles, I don’t usually know how to correctly order my thoughts or what form the finished product will ultimately take. So often, I convince myself beforehand that I have less to say on a certain topic than I actually do. And sometimes, it’s in writing about a subject, and sitting with it more deeply than I ever have, that my thoughts take shape. That rumination helps me to see connections that aren’t always apparent to me as I begin my work.
The exercise is as invigorating as it is vital. And when we follow outlines rather than allow thought to flow organically, it can sap the joy in the creative process. That framework flattens what should be a process of discovery into something fixed and preordained. It assumes our thoughts are settled before they’re given the proper chance to develop and cohere.