College Essay Approach

Wednesday, August 13, 2014 - 16:15

So, how do you feel about Wednesdays?

I’m betting that’s not a question you get asked frequently. It is, however, a past application essay question for the University of Chicago—one of many we’ve amassed in the years we’ve asked “uncommon” questions. Much like your feelings on Wednesdays, we bet you aren’t also often asked about your Ph, your thoughts on odd numbers, or why you’re here and not somewhere else. And, hint: that’s kind of why we’re asking you.

Every year the University of Chicago asks five “uncommon” questions as part of our application supplement. Rather than giving you the same old “what did you do on your summer vacation”-style prompt, we ask our students and alumni to suggest questions they’d like to pose to prospective students, and then consider the over 500 suggestions we get each year among a group of admissions officers before choosing our “final five”. This is how we wound up with this year’s questions, ranging from things like “What’s so odd about odd numbers?” to a quote from an art installation on campus, “Why are you here and not somewhere else?”

We ask you these questions not because we want to fool you, or make you squirm, or hurt your brain. We ask you these questions precisely because we love, love, love seeing where your brain goes when you’re asked a question you’ve never thought about before before. These are the kinds of intellectual encounters you’ll have on our campus every day; it’s rare that a professor will ask you to explain how your loss in the big sports game affected you, but very common for someone to ask you a question you’ve never encountered, and to see how you work with it. The question might be about Plato, or muons, or the work of a beat poet from the South Side in the 1960s instead of about your thoughts on odd numbers—but the ways you’ll be thinking are the same even if not on the same topic, and this, precisely, is why we ask you to try it out as part of your application.  

So how, exactly, do you respond to such an open-ended question? This is, of course, also open-ended. We want you to use this as a time to be creative, to take a prompt and run with it in the way that you think represents what’s going on in your brain best. There are some things we suggest avoiding, and many many things that are totally up for doing. We think our questions are pretty neat, and would love to see what you do with one of them, so we don’t suggest re-using an essay from class, another school, or from your common/universal app personal statement for this essay. We also hope to see students taking this beyond simply factual information about them; a resume is not an essay, so there’s no need to pack all of your achievements and accomplishments in to narrative form. While we welcome fun explorations of new topics, sometimes we do see students who come up with some kind of “schtick” they think helps them stand out (case in point: an essay written entirely backwards, or an acrostic poem). Know that we’re most impressed and influenced by the content, thoughts, and skill contained in your writing rather than tricky tricks, so try not to conflate crazy style with skill—make your essay about the ideas first even if you’d like to explore them in a new way. Some students feel compelled to write about an experience they’ve had or an idea they’re passionate about, and that can be a great choice if you feel the urge. But know that we can often learn a lot about you with how and what you choose to write about even if you’re not writing about yourself, so if you’d like to take this as a time to explore something beyond your own personal experiences, go for it! We read everything and are tickled by lots, and always welcome students who think a little bit outside of the box. So if you’re sitting there thinking “Man, I wish I could write my essay like a critical analysis/book report on Skymall Magazine” (note: this has happened, and the student was admitted) but are shying away because Skymall Magazine isn’t covered in that pulpy book your mom bought you about writing college essays—write about Skymall Magazine! A UChicago supplement essay that responds to our question with a topic you see as interesting and compelling (that is, of course, well thought through and edited reasonably) will shine out much more than following a standard “college essay” format. Don’t be afraid to stretch your mind and have a little fun. That’s what we do here.

And, as a final note: we don’t require your essays to be in a standard 5-paragraph essay format, although we do hope they’ll have words in them (it’s totally fine, although not required at all, to add a visual or musical or any-other-ical accompaniment to your writing, but know we’re also looking at your writing skill here, so we do hope you’ll write something). Some students write personal narratives, some write what could be considered more traditional essay style works, some write short stories, some write something completely different. We ask simply that your essay is somewhere in the realm of 500-650 words, or about 1-2 pages single or double spaced (and we’re flexible—don’t take this as license to write a 14-page tome, but know that we won’t stop reading at 651 words if you need an extra verb).

Any questions? You can always feel free to email us at 

With early decision deadlines inching ever closer, the rush to get those college essays written is real. But fear not, dear applicants! Our Uncommon Essay Approach, will help you can craft winning essays in just 20 minutes a day for 10 days! (Or condense the process and get it done in even less time!) Just follow these easy steps:

1. Find your essay’s purpose.

The essay plays a different role than your grades or test scores. It is your one opportunity to speak to admissions in your own voice – and to jolt them awake from their application-reading-induced slumber. What do you want your essay to tell admissions that they couldn’t learn anywhere else on your application? How will you grab and hold their attention?

2. Review the Common App Prompts.

Even if you have other essays to write for your early decision or early action school of choice, the Common App essay is the place to start. Read through this year’s prompts and wrap your brain around what the questions are really asking. Then, hide them away and don’t look at them again until you have written a draft. At the end of the day what is most important is the story you want to tell. You can almost always back into one of the Common App prompts once you have honed your topic to perfection.

3. Brainstorm your topic.

Stop waiting for divine inspiration. Go out into the world and look for clues. Whether you create lists, take notes on your daily habits, or call up your grandma for ideas, devoting time to brainstorming is the only sure way to uncover your magic topic.

4. Freewrite your heart out.

Once you have brainstormed your way to a magic topic, set aside some time (perhaps three different times throughout the day) to freewrite on what that subject means to you. Get your first thoughts on the page in full and without judgment. Dig for details. You’ll never know what’s inside your brain until you allow it to come out on the page.

5. Sculpt your story.

Review your freewrites and you’ll probably start to notice patterns. What particular moment or individual sticks out in all of your notes? Is there a word or image that seems significant? Use these clues to organize your story into a preliminary outline. We bet you can even pull complete sentences and paragraphs from your freewrites into your first draft.

6. Edit, edit, edit.

How can you make sure that first draft is transformed into a mind-blowingly memorable essay? Read it over at least three times. Edit for story. Then edit for clarity at the sentence level. Finally, edit for grammar.

7. Organize those supplements.

Most supplemental essays fall into one of a few classic categories, so organization is key. If you are applying early to just one school, make sure you do your research thoroughly so you can fill your essay with relevant details. If you are applying to more than one school, group similar assignments together and work on those essays from longest to shortest.

8. Manage your writer’s block.

We know you know that feeling. Your mind is fuzzy. You’re not really feeling like yourself. Every time you sit down in front of the computer your head hurts and your fingers cramp. You can cure this horrible feeling with a few small mental changes. For starters, lower your standards. Not like, forever. Just for the beginning of the process. You will raise your expectations of yourself later as you refine and polish. When you start, quality is not the issue. The issue is that you turn that scary blank page into one filled with ideas.

9. Refer to example essays in moderation.

Poring over dozens of sample college admissions essays immediately before sitting down to write your own can be a debilitating exercise because you may feel compelled to compare your earliest ideas to these final, polished essays. That doesn’t seem fair! That said, we do think that it can sometimes be helpful to read through a few (just a few) to help direct your brain towards the style of the personal narrative.

10. Call for help!

After all of your hard work, if you are still wondering if your topic is worth its weight in hamburgers; if you’re not sure whether your story structure is strong enough to support your big idea; even if you’re just wondering whether or not your overall story will create enough fireworks to hold the attention of an admissions advisor for your allotted two minutes of admissions essay fame, CALL US! Or email us: We will personally extract the winning ideas from your noggin with our magic powers (of conversation).

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