How To Answer A Crazy Essay Question On A College Application

We recently showed you some of the craziest essay prompts from college applications in which students are asked to ponder everything from giant mustard containers to the potential difficulties of being green.

University of Chicago is perhaps the most notorious college to make their applicants really get creative, and in past years have asked students "Find X" and "So where is Waldo, really?"

In past years UChicago has asked students such questions as:

• So where is Waldo, really?
• Find X
• "Have you ever walked through the aisles of a warehouse store like Costco or Sam's Club and wondered who would buy a jar of mustard a foot and a half tall? We've bought it, but it didn't stop us from wondering about other things, like absurd eating contests, impulse buys, excess, unimagined uses for mustard, storage, preservatives, notions of bigness…and dozens of other ideas both silly and serious. Write an essay somehow inspired by super-huge mustard."

We spoke to UChicago admissions officer Garrett Brinker — who graduated from the school in 2010 — about the art of crafting an essay prompt and some tips for aspiring essay writers. Here's what we learned:

There's no model answer.

Essay prompts are crowd-sourced by the admissions office to current UChicago students and young alumni. While Brinker says they tend to receive hundreds of responses, admissions officers usually choose around five different prompts from the submissions.

"We are at liberty to lightly edit the essay prompts in order to give students additional intellectual freedoms or possibly spur their intellectual creativity a bit more, but there’s not necessarily one or two or even ten types of model answers that we’re envisioning throughout this process," Brinker says.

Take your time.

An aspect of your essay that doesn't appear on the page actually might be the most important. Although Brinker says that there are "literally thousands of ways to write a successful essay," an admissions officer may actually read thousands of essays each year.

With this kind of volume, "one quality that stands out is simply time—the amount of time that you spent on your essay," Brinker says. "Because we read so many essays, it does become evident to us when a student has spent a total of only a couple hours on their essay, and when a student has spent a lot more time on that essay."

Have fun.

While this might seem a little cliche, Brinker tells us that having fun while writing your college essay may have a broader benefit than just making the application process a little less stressful. Brinker says that from an admissions officer's perspective, "if students have fun writing them, we will have fun reading them."

Write about yourself.

Even though UChicago sees an exceptional amount of diversity in how applicants answer their prompts, no admissions officer has a favorite "type" of essay, according to Brinker. "Some good essays are funny, others are serious, and still others are sarcastic, witty, and deeply personal, all at the same time. But overall, our favorite essays are ones that are thoughtful and truly tell us something about you as an individual," he says.