2020-21 University of Chicago Supplemental Essay Prompts & How to Approach Them

UChicago Wants to Know How You Think

“Do you feel lucky? Well, do ya, punk?” ~ Eleanor Roosevelt.

Eleanor Roosevelt didn’t really say that, at least in public — as far as we know, but one of the supplemental essay prompts on this year’s Chicago application is to “Misattribute a famous quote and explore the implications of doing so.”

If that prompt doesn’t do it for you, how about this one? “What can actually be divided by zero?”

Or maybe this one:

“Who does Sally sell her seashells to? How much wood can a woodchuck really chuck if a woodchuck could chuck wood? Pick a favorite tongue twister (either originally in English or translated from another language) and consider a resolution to its conundrum using the method of your choice. Math, philosophy, linguistics… it’s all up to you (or your woodchuck).”

There’s no word limit on these essays, and there are many more prompts to choose from, including ones from previous years — and quite a few of them are based on student ideas, including an idea from Chicago grad (’51) Susan Sontag. TO READ ALL OF THEM AND THE SECOND REQUIRED PROMPT, VISIT THE UC WEBSITE.

There’s no word limit on these essays, but if you aim for 500 words, you’ll be OK. More important than length is what you write — which you can translate to: how you think.

These instructions on the U Chicago website put the assignment nicely:

“We think of them as an opportunity for students to tell us about themselves, their tastes, and their ambitions. They can be approached with utter seriousness, complete fancy, or something in between.

“Each year we email newly admitted and current College students and ask them for essay topics. We receive several hundred responses, many of which are eloquent, intriguing, or downright wacky.”

Supplemental essay prompts are a dialogue between the university and the applicant. If you read the Chicago essays and they leave you cold, feeling alienated or completely uninterested, take your feeling seriously. This may not be the right college for you — and that’s OK. There are hundreds more to choose from. But if even one of these many prompts, from this year or any of the previous years, is exciting to contemplate and fun to write — go for it. And don’t forget there’s another prompt from UC, also required, that some find more difficult — and much less creative:

How does the University of Chicago, as you know it now, satisfy your desire for a particular kind of learning, community, and future? Please address with some specificity your own wishes and how they relate to UChicago.

For help with these essays or any others, please contact me by email or phone (East Coast Time Zone). Liz@DontSweatTheEssay.com or 1-855-99-ESSAY.

And thanks for stopping by.

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  1. Best Ever University of Chicago Application Essay Prompts 2020-21 – College Essay Consultant ~ My unique, innovative, highly personal approach helps students applying to Harvard, Yale, MIT, Brown & other top colleges, medical & law schools ~

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