The Five Things Essay

An all-purpose writing prompt to help you find your voice, lose your voice, beat writer's block, or figure out what the hell you want to write about in the first place.

The is your brain on the Five Things Essay (Getty).

What Is A Five Things Essay?

A Five Things Essay, or a Five Things draft, is an all-purpose writing prompt to help you find your voice, lose your voice, beat writer's block, or figure out what the hell you want to write about in the first place. Structurally, it is a piece of nonfiction writing, published or unpublished, that either a) includes a numbered list of five sections, or b) was originally written as a numbered list of five sections, before being edited into a more cohesive whole.

It does not have to have five paragraphs or five topics. The number five functions more like five little shoves to keep you thinking, to keep your pen moving across the page or your fingers on the keyboard.

Where Does The Five Things Essay Come From?

Back in the misty olden days of writing on the Internet (i.e., some time around 2013 or so), writers I followed online would often share posts on Tumblr or other blogs that were structured around a numbered list of five things. These “things” usually included a mix of observations, thoughts, confessions, memories, recommendations, or questions, each ranging in length from many paragraphs to just one short sentence apiece.

I don’t know who, if anyone, originated the form. It may have come from LiveJournal blogs of the early 2000s, out of which emerged a popular type of entry called Five Things Make a Post. Or it might have been adapted from a fanfiction trope that goes back at least to the early 1980s, called Five Things, or Five Times. Or it may have developed separately, a kind of writerly convergent evolution, a carcinization of words, like the way different animals keep independently evolving into the shape of crabs over and over again in the dark depths of the seas. Creatures forged by the same environmental pressures.

Why Five Things?

I don’t know. There seems to be something about the number five that helps give a satisfying structure—at least to the writer, if not to the reader. But maybe there is something special about the number five, too. In mathematics, five is both the first good prime, and the first safe one. We have five senses, five basic tastes, and five fingers on each hand. The human body, with arms and legs outstretched like those of Leonardo da Vinci’s Vitruvian Man, resembles a five-point star, a symbol of wholeness, nature, and divine blessing to Pythagorus and his followers. The pentagram is an infinitely self-regenerating shape in which can be found the golden ratio, long believed by philosophers and artists to possess the secret to aesthetic harmony. There are Five Pillars in Islam, five books in the Torah, five wounds on the body of Christ, and five faces attributed to the god Shiva. In the cosmology of the ancient Greek philosopher Pherecydes of Syros, the God of Time distributed his seed—a “watery chaos”—into the five recesses of existence so that the cosmos could be born.

How Do I Write A Five Things Essay?

There are certainly many ways to write an essay based on a numbered list of five things, but this is how I write them.

Start by writing down the number 1, like you’re beginning a list. Then write the first thing that comes to mind. To borrow from Ernest Hemingway, write one true sentence. Hemingway says to write “the truest sentence that you know,” but this might be intimidating to the overthinkers among us. Just quiet your mind for a moment and then write the first true thing that comes to you. Something you’ve been thinking about. Something you noticed or saw. There is no need for explanation or preamble—just dive right in. There are no wrong or stupid choices. Write one true sentence, and then see if there is another sentence that wants to come after it. Keep writing until you come to the end of this particular thought, whether it’s one line, a paragraph, a whole page, or even more.

Regardless of length, when you’ve finished with the first thing, simply make a new paragraph, write the number 2, and start again. This second thing can flow thematically from what you’ve just written, or it can be wildly unconnected, coming entirely out of left field. Maybe they are connected but you don’t realize why just yet. Don’t stop to ask questions, just go wherever your mind takes you. Trust the intuitive, connective tissue of the writing process. It doesn’t have to make sense just yet. Rather than complaining, or bemoaning our to-do list, we’re placing five found objects inside a box, like stones or shells found on a hike or a beach walk. Keep going until you’ve finished writing your third, fourth, and fifth thing.

At the end, read through what you’ve written and see of you can spot any themes that might connect the different points. After letting the draft rest for a while—hours, days, weeks, months, whatever you prefer—you can come back and start to edit. If you want to keep the numbers, feel free to cut or add in large sections as you see fit. Rearrange the order. Elaborate and remove. When I was doing this exercise every day, my edited drafts usually ranged between 800 and 1,200 words. Leaving in the numbers may help tie together a piece that doesn’t naturally flow from topic to topic, but you can also take the numbers out, combine it with other Five Things Essay drafts, or, really, do with it whatever you want. The numbers are only training wheels, and for most work that you intend to publish, the time will come to take them off.

A Prompt For Writers Who Don’t Like Prompts

There is another option for the rough drafts of your Five Things Esssays, which is to put them aside unedited and use them later as personalized prompts. I don’t usually like to use outside prompts. Maybe it’s the rebel in me, but whenever I’m explicitly told to write about something in the context of a workshop, to describe the house I grew up in, or tell the story of a lesson I learned, something in me freezes up. With the Five Things exercise drafts however, I can revisit them when I’m looking for something to write about, and there they will be, a cache of lines and paragraphs to be used as a jumping off point. For me at least, these are usually more creatively fruitful and less mundane than a traditional free-form diary, which so often fills up with daily anxieties and chores, that revisiting it can feel more distressing than inspiring.

It’s okay if you repeat yourself, write badly, or have no idea where you’re going with any of this. In fact, it is encouraged. This is an exercise for putting thoughts down on the page, not for crafting pretty sentences. Not yet, anyway.

Write like nobody is watching.

Because nobody is watching.

Happy writing, and good luck.

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