Application Essay Tips from John Kennedy Toole

I touch the books. When I’m in the bookstore, I pull the books off the shelves, open to the first chapter, and see if the author can make me turn the page. Last night, in my search for more application essay tips, I undertook this exercise with my books at home. The eighth and final book I pulled down was John Kennedy Toole’s novel A Confederacy of Dunces. Today's application essay tips come from these three sentences:

“A green hunting cap squeezed the top of the fleshy balloon of a head. The green earflaps, full of large ears and uncut hair and the fine bristles that grew in the ears themselves, stuck out on either side like turn signals indicating two directions at once. Full, pursed lips protruded beneath the bushy black moustache and, at their corners, sank into little folds filled with disapproval and potato chip crumbs.”

5 Application Essay Tips from A Confederacy of Dunces

What application essay tips can we learn from three sentences? Here are five to consider:

Application Essay Tips | Tip #1: Use vivid verbs.

Look at the verbs Toole uses. Squeezed. Stuck out. Protruded. If you only showed me these verbs, and nothing more, I’d still want to read on. Each of these verbs communicates a sense of things being out of place, which makes me want to know more about this weirdo in the green cap.

To upgrade your verbs, start by circling them. Then examine each to see if you can find a better alternative. When you’ve eliminated all (or nearly) all uses of “has” and “is,” and when you’ve avoided repeating verbs, you’ve improved your essay’s verbs.

Application Essay Tips | Tip #2: Find a different perspective.

In the opening, Toole is just telling us that a guy with a big head and lots of hair is wearing a funny green hat. Big deal. The big deal, actually, is that Toole makes the mundane interesting. That’s the same challenge you have when you write your application essay. Your essays will cover topics admission officers have already seen, so your goal is to make the ordinary fresh.

Toole makes the ordinary fresh by taking a different perspective. Normally, we think of people wearing hats, but Toole describes a hat squeezing someone’s head. Normally, we think of a person’s face as a single unit, but Toole describes the protagonist’s face as a collection of some of its component parts: large ears, uncut hair, fine bristles, pursed lips, and bushy moustache.

How do you find your new angle on a familiar topic? First, figure out the conflict your essay will describe, whether between you and yourself, you and another person, or you and an external obstacle. (Remember, conflict is the key to a good story!). Second, try to frame your conflict in a less obvious way. That is, if the obvious description of the conflict is between you and yourself, see whether you can instead frame the conflict as between you and an external obstacle.

In my admission essay, I wrote about a cross country race (I know – boring!) as a conflict between me and an external obstacle: the course. But I could have written a better essay if I had framed the race as a conflict between me and another person: my coach, or perhaps a teammate. If you avoid describing your conflict in an obvious way, you can develop a fresh take on a familiar subject.

Application Essay Tips | Tip #3: Use a simile.

The fantastic feature of similes (comparisons that use “like” or “as”) is that they require you to use an image, which immediately makes your writing more interesting. Toole writes that the ear flaps of the protagonist’s cap “stuck out on either side like turn signals indicating two directions at once.” Anyone who’s driven a car can picture these ear flaps sticking straight out from the main character’s head. And anyone who’s paying attention can appreciate that the reference to two turn signals suggests the main character is experiencing an internal conflict. When you choose the image for your simile, make sure you select one that both shows how clever you are and reveals something deeper about your outlook on life.

Application Essay Tips | Tip #4: Surprise the reader.

If you want to delight your reader, surprise her. Toole surprises the reader by describing the corners of the main character’s lips as being filled with “disapproval and potato chip crumbs.” What’s the surprise? The surprise is that Toole’s description combines an assessment of the protagonist’s mental condition, disapproval, with his physical condition, potato-chip-crumb-covered lips. Seeing disapproval and potato chip crumbs together is funny because it's unexpected. Any time you can set the reader up (for example, by leading her to believe you're writing just another "death of a loved one" essay, just another "how I won the big game" essay, or just another "trip to impoverished country" essay) and then undermine her expectations (by putting a twist on an ordinary topic), you're on your way to surprising the reader.

Application Essay Tips | Tip #5: Use alliteration.

A little alliteration won't rescue a doomed essay, but it will give your writing some pizzazz. And it's easy. Need I say more? In Toole's three intro sentences, I see "pursed lips protruded," "bushy black" moustache, and "folds filled" with disapproval. When you challenge yourself to use alliteration, you'll think more about what words you're using and why, a process that will benefit your style.

Well, who knew we'd find five application essay tips in three sentences of American fiction? But we did. If you liked today's application essay tips, please share them with your friends. Thank you!


Jon Perkins holds a B.A. in English from Stanford University and a J.D. from Harvard Law School. He helps students with their college, law school, and medical school applications.