How to Answer the University of Chicago Supplemental Essay Prompts

You might assume that college essay supplements are merely an opportunity for a college to learn more about its applicants; that they are known to students only after they’ve made a decision to apply to a particular university; that they are rooted in some important academic or cultural aspect of the institution with which they are associated. For nearly every college, you’d be right. But not so for the University of Chicago. For the University of Chicago, the extended essay is a marketing tool and a warning—a declaration to prospective students that the institution is seriously intellectual and, just as frequently, seriously unserious. The release of the extended essay questions each fall is a notable event in the world of college admissions, where counselors are as often intrigued as they are annoyed at the year’s brand new set of complex thought experiments, unusual juxtapositions, and portmant-odes to pop culture. Did you roll your eyes at that pun? The University of Chicago may not be right for you. If you’re willing to read on, however, we can help. First, the basics: the University of Chicago essay supplement is split into two assignments. The first of these is a rather typical question about your interest in the university, and ought to be approached as such. You’re expected to look forward to opportunities at Chicago and how you’ll take advantage of them, given your desire for a particular kind of place. This essay ought to be deeply thoughtful and personal, and I believe it must recognize and embrace the ubiquitous intellectual curiosity and intense rigor of the Chicago program. An under-researched love letter to the Windy City just won’t do. The second assignment is where students are most frequently challenged, and understandably so. Within this assignment, you have two equally important tasks: choose a prompt, and write a response to it. While it would seem that the writing of the prompt is the more important thing, I find students often struggle more with the choosing. To make this process serve you, you ought to consider not only the five options for your year, but also the library of options from years prior. Pull out three to five that you find you’re most immediately drawn to, for any reason at all. What do you like about these questions? What sorts of intellectual associations do you find yourself making? What are some promising insights that you might have that may be unique to you? Sketch out a rough outline for these three to five prompts, with your main idea and some supporting content that will keep the response fresh and engaging. For prompts that ask you for a short answer, like this year’s Essay Option 3, which asks you to first coin your own word and then share its meaning and plausible use, be sure that the answer itself is interesting prima facie. Your reader should smile at your short answer before they launch into your narrative explanation: “hey, that’s clever.” If it helps, imagine yourself in a University of Chicago common room late at night, discussing all manner of strange questions with your new freshman classmates. When one of them poses an off-the-wall question, your initial answer should inspire interest and further conversation, lest the group move on to a different subject altogether. As you begin drafting your response to your chosen prompt, take risks. You’ll win no allies in the admission office by writing a typical essay, presenting obvious commentary on contemporary society, or reusing an essay you’ve written for another school. Remember that, while Chicago students often describe their university as “the place where fun goes to die,” the reality is that they engage in a kind of unusually intellectual fun that very few academic masochists will enjoy—and they love every minute of it. That’s the sweet spot for your essay. So put on a pot of water, boil your noodle, and throw ideas at the wall until you see what sticks.