When my second year of high school finished and my older sister began touring colleges, there was a noticeable shift in the discussions surrounding my and my sister’s lives. Up to that point, our lives were measured in report cards, band concerts and soccer games. Suddenly, these milestones felt almost childish in comparison to the lofty phrases like “setting yourself up for the future” and “figuring out what you want to do with your life” that were being thrown around.

By the time it was my turn to apply for college, I had heard all the typical advice twice over: make sure to have a backup school, spend extra time to craft your applications thoughtfully, get trusted reviewers to look over your essays, and, of course, consider your choices carefully. After all, those applications were expensive—to say nothing of the financial or temporal cost of wasting time at the wrong school. All in all, I think I leveraged this advice well and ended up with a set of sensible applications to a sensible number of sensible schools that I chose for sensible reasons—except for one.

The University of Chicago is a phenomenal school. It has superb academics, great financial aid and beautiful architecture; conveniently, it’s even located a short train ride away from my childhood home. I didn’t want to attend in the slightest.

Sure, I would have been proud to get into such a prestigious school, and, under the right circumstances, I may even have matriculated, but I really didn’t want to stay in the Midwest for college or spend four years in a rather less than ideal area in a giant city. I’d like to say that I applied for a respectable reason like walking in the footsteps of Carl Sagan and Edwin Hubble, but my true reason was almost as silly as wanting to eat in the Hogwartian dining hall: I wanted to write their admissions essay.

Each year, the University of Chicago petitions their students for creative essay topics that are included in their undergraduate admissions application. Partly because I like a good challenge and partly due to a newfound love of writing—thanks Mr. Monday!—I really wanted to take a crack at whatever UChi could throw at me.

Not knowing what to expect, I finished the Common App and the supplements for my other schools; that way, I surmised, I wouldn’t have any higher priority applications hanging over my head while I worked on the fun stuff. When I finally clicked through to that Chicago’s essay, I was greeted by a prompt short enough to start a haiku:

How did you get caught?1

I was relieved that the prompt wasn’t entirely open-ended, but I was also a little disappointed: it seemed easy. I surprised myself with how quickly I came up with an answer and wrote about how I got “caught” by music and very suddenly transitioned from owner of a single Aaron Carter CD to a melomaniac and collector of old records. I even went out on a limb and put my iPod on shuffle and wrote a brief blurb about how the first few songs had caught me in their own unique ways.

I had a great deal of fun writing that essay (and even more fun attending a school that was not the University of Chicago!), but I got wrapped up in my impending graduation and forgot about it rather quickly. Now that I’m finally taking my writing skills (or lack thereof) out for another spin with this blog, I’ve noticed that it was a much better prompt than I had originally realized.

Revisiting this prompt has reminded me of all the many ways I’ve been “caught” in the past six years. From Southern biscuits, strawberry black pepper ice cream and bourbon cream to board games, comic books and new Disney movies to swing dancing, long walks and new friends, I’ve been captivated by quite a number of wonderful things since I submitted that less than sensible application to the University of Chicago. Thank you, Kelly Kennedy, University of Chicago Class of 2010,2 for your wonderful prompt—six years later, it’s allowed me to revisit some of my fondest memories under a new lens, and that’s something I’m truly grateful for.


  1. Okay, technically the whole prompt was How did you get caught? (Or not caught, as the case may be), but, hey, poetic license.

  2. See here for the attribution.