Application and Essay Tips

Supplemental Essay “Fun”

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We’ve discussed supplemental essays before here on Admit This! Well, we’re going to discuss them again today! For those of you unfamiliar with the term “supplemental essay” as it relates to college admissions, allow me to explain. I’ll make an analogy with an old movie marketing line.

Back in 1975, a blockbuster movie about sharks came out. Jaws started the whole shark-mania thing that we read about and see so much of on TV these days. Anyway, when Hollywood marketers were teasing the Jaws premiere, they used a memorable tagline: Just when you thought it was safe to go back in the water. That line was accompanied by a picture of the legendary, huge, ferocious shark that terrorized moviegoers across the world back then and still does today.


My take on that tagline and its link to the college process goes something like this: “Just when you thought you were done with your Common Application essay …” Here come the supplemental essays! You may have worked long and hard on creating the perfect Common App essay, addressing the perfect prompt for you. Then, just as you sit back, relax, and exhale, you suddenly see something like this -- more essays requiring you to answer university-specific questions, typically in about 300 or fewer words.

It’s kind of like screaming, “SHARK!!!” as you see a dorsal fin angling toward you the moment you wade into the warm waves along Daytona Beach. “Now what?!” you moan.

Congratulations. You have just encountered a typical supplemental essay assignment … just when you thought it was safe to rest your brain from essay writing! Fear not, though. You’re not alone, not by a long shot. There are much bigger sharks than those that ask about an engineering project or your favorite word.

For example, take the University of Chicago’s infamous supplemental essay prompts. Let’s take a look at some of the 2018-2019 shiver (yeah, that’s what you call a group of sharks -- I looked it up), along with some of my usual wry observations, which might serve to inspire some of your own supplemental creativity, not only for those of you applying to the University of Chicago but also to any other school requiring additional writing beyond the Common Application requirement:

Question 1 (Required)

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.

This is your standard “Why this school?” question that many colleges ask. They want to see if your motivations to attend go deeper than what you’ve seen in a brochure or internet virtual tour. Drill down through a school’s website to find the gold you need to answer these types of questions.

Question 2: Extended Essay (Required; Choose one)

Don’t you just love that word “extended”? This is the BIG one -- get ready to strut your imaginative stuff!

Essay Option 1

In 2015, the city of Melbourne, Australia, created a "tree-mail" service, in which all of the trees in the city received an email address so that residents could report any tree-related issues. As an unexpected result, people began to email their favorite trees sweet and occasionally humorous letters. Imagine this has been expanded to any object (tree or otherwise) in the world, and share with us the letter you’d send to your favorite.

- Inspired by Hannah Lu, Class of 2020

I would establish a “pothole-mail” service so that we poor drivers could send outraged messages to our local highway department officials about those giant roadway craters that nullify our cars’ front-end alignments, splash coffee on our deluxe leather seats and elicit sailor-like curses from our normally civilized vocabularies. The respective pothole “mail” addresses could be spray painted in day-glow orange paint beside each indentation on the roadway surface. That would add an element of colorful diversity to offset the mundane concrete beige.

Essay Option 2

You’re on a voyage in the thirteenth century, sailing across the tempestuous seas. What if, suddenly, you fell off the edge of the Earth?

- Inspired by Chandani Latey, AB 1993

This is a golden opportunity to tout both your vast knowledge of planetary anti-spherism and your membership in The Flat Earth Society! You could also express your righteous indignity about this prompt’s implication that the Earth is, indeed, round and that “flatism” has been relegated to the dungeons of Middle Ages thinking!

Essay Option 4

Lost your keys? Alohomora. Noisy roommate? Quietus. Feel the need to shatter windows for some reason? Finestra. Create your own spell, charm, jinx or other means for magical mayhem. How is it enacted? Is there an incantation? Does it involve a potion or other magical object? If so, what's in it or what is it? What does it do?

-Inspired by Emma Sorkin, Class of 2021

This is easy. Flushinto! The magic word that instantly does away with annoying supplemental essays. The only “magic object” required is the “delete” button on your computer keyboard. As you scan the application requirements of your favorite colleges and you come across a statement that says something like ...

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.

… all you have to do is highlight the complete portion of supplemental essay requirements on the application page, sit up straight, inhale a hearty breath and distinctly yell, “Flushinto!” as you simultaneously press the delete key. The power of this magical maneuver is so enjoyable that not only will the offending essay requirements be gone but their disappearance will be accompanied by a stentorian flushing sound, similar to those turbo-flush toilets we encounter in public buildings. WARNING: Check your computer speakers’ volume levels before invoking this handy fix.

 Essay Option 5

Imagine you’ve struck a deal with the Dean of Admissions himself, Dean Nondorf. It goes as follows: You’re guaranteed admission to the University of Chicago regardless of any circumstances that arise. This bond is grounded on the condition that you’ll obtain a blank, 8.5 x 11 piece of paper, and draw, write, sketch, shade, stencil, paint etc., anything and everything you want on it; your only limitations will be the boundaries of both sides on the single page. Now the catch… your submission, for the rest of your life, will always be the first thing anyone you meet for the first time will see. Whether it’s at a job interview, a blind date, arrival at your first Humanities class, before you even say, “hey,” they’ll already have seen your page, and formulated that first impression. Show us your page. What’s on it, and why? If your piece is largely or exclusively visual, please make sure to share a creator's accompanying statement of at least 300 words, which we will happily allow to be on its own, separate page.   

PS: This is a creative thought experiment, and selecting this essay prompt does not guarantee your admission to UChicago.

-Inspired by Amandeep Singh Ahluwalia, Class of 2022

My page would say, “My father is a multi-billionaire and I am his agent to help him fund any need or cause. Let’s talk.”

Essay Option 6

In the spirit of adventurous inquiry, pose your own question or choose one of our past prompts. Be original, creative, thought provoking. Draw on your best qualities as a writer, thinker, visionary, social critic, sage, citizen of the world or future citizen of the University of Chicago; take a little risk, and have fun.

My question would be: “Using between 750 and 5,000 words, explain why supplemental essays should not be part of the Common Application process.”

The above is my way of preparing you college-bound high school seniors for what may possibly await as you enter the college process this fall. Obviously, your supplemental writing requirements probably won’t be like those of the University of Chicago, but you should be expecting some kind of add-on essay.

It’s all part of the fun of college admissions. Fire up your imagination, have fun and watch out for those potholes!