Difficult College Essay Questions

As a college consultant, I have become intimately familiar with numerous supplemental college essay questions. While many prompts seem doomed to elicit responses that are conventional clichés, others are bound to spark creativity, and hopefully evoke genuine self-discovery, for the motivated applicant.

In no special order, here are ten of my “faves”, with musings about how I might try to respond to these thought-provoking questions:

1. Imagine that you have the opportunity to travel back through time. At what point in history would you like to stop and why?(Swarthmore College) How fun is this? It’s like Peabody & Sherman’s WABAC Machine! I want to apply to Swarthmore myself, just to write this essay. Would I wish to be among the crowd on the Via Dolorosa that fateful Friday afternoon, two millennia ago? Stand as a spectator on the Tower Green as Anne Boleyn forgives her executioner, the swordsman from France? Be aboard the ill-fated Titantic that freezing night in April, deciding whether to step into a lifeboat or remain on deck with my husband? In my family, filled with history buffs, this essay prompt could be an exciting after-dinner game.

2. Select a creative work — a novel, a film, a poem, a musical piece, a painting or other work of art — that has influenced the way you view the world and the way you view yourself. Discuss the work and its effect on you. (New York University)

My choice would have to be David O. Selnick’s epic film that brought to life Margaret Mitchell’s 1936 novel, Gone with the Wind. I have always admired survivors of civilizations that were totally disassembled and reconstructed in a new way, such as my parents and in-laws living through the Great Depression. I occasionally wonder how I would fare if today’s way of life was suddenly forever changed. Further, Mitchell’s insightfully crafted immortal characters are archetypes that offer wisdom into the human condition; they have become lifelong tools for analyzing my own motivations and the roles others play in my life.

3. If you were to describe yourself by a quotation, what would the quote be? Explain your answer.(Dartmouth College) As a fantatical “quotaphile,” I would find this choice overwhelmingly difficult. It would be tough to select from the wise and witty sayings of Shakespeare, Churchill, Einstein, or Wilde. But since the quotation has to describe oneself, as a lover of the mysteries of the psyche, I would probably choose  Carl Jung‘s observation: “Who looks outside, dreams; who looks inside, awakes.”

4. If you could go back and change one day in your life, what would you change and why?(Santa Clara University) This prompt brings to mind the intrguing award-winning movie, Sliding Doors, starring Gwyneth Paltrow, which explores the concept of whether we make our fate by specific actions, or whether there is a destiny dynamic at work that prevails despite our actions. In my 56 years on the planet, I have come to subscribe to the latter view, so it would be difficult for me to answer this question. I would probably choose to discuss my ideas about free will, random events, serendipity and destiny.

5. If you had a day to spend as you wish, how would you use your time?(Carleton College) Wow. An applicant’s answer to this question would be truly revealing. I remember watching a Twilight Zoneepisode as a kid (“Time Enough at Last”), in which a bookworm is the sole survivor of a nuclear apocalpyse, finally having time enough to pursue his passion: reading (and of course, in Rod Serling‘s nightmare world, his Coke bottle thick spectacles break on the steps of the library). I would spend my “day” similarly (without the broken glasses!), either reading or writing, and I guess that reveals quite a bit about me. How your student would describe his or her perfect day would reveal much as well.

6. If you were to develop a Mt. Rushmore representing the 20th century, whose faces would you select and why?(College of William and Mary) This question reveals one’s philosophy of life, ideas on leadership and heroism, value system, and perhaps, one’s politics. Not to mention a knowledge of American history. For me, the four heroic leaders, Democrat and Republican, black and white, would be:

President Dwight D. Eisenhower, whose bold brilliance as the architect of D-Day turned the tide of the war against Hitler; President John F. Kennedy, whose leadership during the Cuban missile crisis may have saved the world; Dr. Martin Luther King, Jr., whose non-violent leadership of the civil rights movement ushered in a great step forward for racial equality in our nation; and President Ronald Reagan,whose assertion of his passionate beliefs in American exceptionalism, personal liberty and limited government led to the dissolution of the Soviet Union and decades of U.S. economic prosperity and innovation. Whom would you choose?

7. Recall a compliment you received that you especially value. What was it? From whom did it come? (Yale University) A dear and wise old friend, whom I greatly respect, met many of my long time friends at my fiftieth birthday party a few years ago. After the soirée, she observed, “All your friends that I met told a story of how you had helped them with something, like the courage to start a new business, or the strength to get through a personal tragedy.” Thank God. This meant more to me than any compliment on raw talent or professional accomplishment, because it affirmed my own values about helping others to find their way. If I can accomplish this goal, I will feel that my life has been a success.

8. If you founded your own college or university, what topic of study would you make mandatory for all students to study and why? What would be the values and priorities of your institution and why?(Lehigh University) Several years ago, one of my clients answered this prompt by calling her institution “Altruism University,” requiring that all students learn about compassion and engage in community service. This exceptional young woman was of Indian descent and was a fervent adherent of Jainism, the non-violent, altruistic religion of Mohandas Gandhi. Her essay revealed much about her inspiring value system. What admissions officer wouldn’t want a student like this in the campus community?

9. “Don’t play what’s there, play what’s not there.” – Miles Davis. What does this quote mean to you?(University of Chicago) I believe this question is about uniqueness. A student’s contribution to the world is not about doing something no one else has ever done before; it is about doing what perhaps many people have done, but in one’s own special way.

10. Why did you do it?(Tufts University) Tufts always takes the prize for the most amazing, thought-provoking questions. How would you answer that?

My rule of thumb for “fave-ing” a college essay prompt is: would I myself be eager to roll up my sleeves and answer that question? Would it really make me think, look within myself, and respond from the heart? Or would I simply roll my eyes and start typing a perfunctory response, immediately knowing what the “right” answer is to a simplistic, stereotypic question?

Your teen may not be interested in applying to  schools that happen to write the most provocative essay questions. But it might be a thought-provoking exercise to kick around some of these questions on a long family drive, to stimulate reflection for your high school student (and everyone else in the family). Future essay writing may be easy after taking on these challenging questions!

If you have come across a provocative essay prompt you would like to share, please feel free to comment.

On November 5, 2011   /  12th Grade, College Admissions, College Essays  

Some classic questions from previous years…

Joan of Arkansas. Queen Elizabeth Cady Stanton. Babe Ruth Bader Ginsburg. Mash up a historical figure with a new time period, environment, location, or occupation, and tell us their story.
—Inspired by Drew Donaldson, AB'16

Alice falls down the rabbit hole. Milo drives through the tollbooth. Dorothy is swept up in the tornado. Neo takes the red pill. Don’t tell us about another world you’ve imagined, heard about, or created. Rather, tell us about its portal. Sure, some people think of the University of Chicago as a portal to their future, but please choose another portal to write about.
—Inspired by Raphael Hallerman, Class of 2020

What's so odd about odd numbers?
–Inspired by Mario Rosasco, AB'09

Vestigiality refers to genetically determined structures or attributes that have apparently lost most or all of their ancestral function, but have been retained during the process of evolution. In humans, for instance, the appendix is thought to be a vestigial structure. Describe something vestigial (real or imagined) and provide an explanation for its existence.
—Inspired by Tiffany Kim, Class of 2020

In French, there is no difference between "conscience" and "consciousness." In Japanese, there is a word that specifically refers to the splittable wooden chopsticks you get at restaurants. The German word “fremdschämen” encapsulates the feeling you get when you’re embarrassed on behalf of someone else. All of these require explanation in order to properly communicate their meaning, and are, to varying degrees, untranslatable. Choose a word, tell us what it means, and then explain why it cannot (or should not) be translated from its original language.
– Inspired by Emily Driscoll, Class of 2018

Little pigs, French hens, a family of bears. Blind mice, musketeers, the Fates. Parts of an atom, laws of thought, a guideline for composition. Omne trium perfectum? Create your own group of threes, and describe why and how they fit together.
– Inspired by Zilin Cui, Class of 2018

The mantis shrimp can perceive both polarized light and multispectral images; they have the most complex eyes in the animal kingdom. Human eyes have color receptors for three colors (red, green, and blue); the mantis shrimp has receptors for sixteen types of color, enabling them to see a spectrum far beyond the capacity of the human brain. Seriously, how cool is the mantis shrimp: mantisshrimp.uchicago.edu What might they be able to see that we cannot? What are we missing?
–Inspired by Tess Moran, AB'16

How are apples and oranges supposed to be compared? Possible answers involve, but are not limited to, statistics, chemistry, physics, linguistics, and philosophy.
–Inspired by Florence Chan, AB'15

The ball is in your court—a penny for your thoughts, but say it, don’t spray it. So long as you don’t bite off more than you can chew, beat around the bush, or cut corners, writing this essay should be a piece of cake. Create your own idiom, and tell us its origin—you know, the whole nine yards. PS: A picture is worth a thousand words.
—Inspired by April Bell, Class of 2017, and Maya Shaked, Class of 2018 (It takes two to tango.)

"A man cannot be too careful in the choice of his enemies." –Oscar Wilde. Othello and Iago. Dorothy and the Wicked Witch. Autobots and Decepticons. History and art are full of heroes and their enemies. Tell us about the relationship between you and your arch-nemesis (either real or imagined).
–Inspired by Martin Krzywy, AB'16.

Heisenberg claims that you cannot know both the position and momentum of an electron with total certainty. Choose two other concepts that cannot be known simultaneously and discuss the implications. (Do not consider yourself limited to the field of physics).
–Inspired by Doran Bennett, BS'07

Susan Sontag, AB'51, wrote that "[s]ilence remains, inescapably, a form of speech." Write about an issue or a situation when you remained silent, and explain how silence may speak in ways that you did or did not intend. The Aesthetics of Silence, 1967.
–Anonymous submission

"…I [was] eager to escape backward again, to be off to invent a past for the present." –The Rose Rabbi by Daniel Stern
Present: pres·ent
1. Something that is offered, presented, or given as a gift.
Let's stick with this definition. Unusual presents, accidental presents, metaphorical presents, re-gifted presents, etc. — pick any present you have ever received and invent a past for it.
—Inspired by Jennifer Qin, AB'16

So where is Waldo, really?
–Inspired by Robin Ye, AB'16

Find x.
–Inspired by Benjamin Nuzzo, an admitted student from Eton College, UK

Dog and Cat. Coffee and Tea. Great Gatsby and Catcher in the Rye. Everyone knows there are two types of people in the world. What are they?
–Inspired by an alumna of the Class of 2006

How did you get caught? (Or not caught, as the case may be.)
–Proposed by Kelly Kennedy, AB'10

Chicago author Nelson Algren said, "A writer does well if in his whole life he can tell the story of one street." Chicagoans, but not just Chicagoans, have always found something instructive, and pleasing, and profound in the stories of their block, of Main Street, of Highway 61, of a farm lane, of the Celestial Highway. Tell us the story of a street, path, road—real or imagined or metaphorical. 
–Anonymous submission

UChicago professor W. J. T. Mitchell entitled his 2005 book What Do Pictures Want? Describe a picture, and explore what it wants.
–Inspired by Anna Andel

"Don't play what's there, play what's not there."—Miles Davis (1926–91)
–Inspired by Jack Reeves

University of Chicago alumna and renowned author/critic Susan Sontag said, "The only interesting answers are those that destroy the questions." We all have heard serious questions, absurd questions, and seriously absurd questions, some of which cannot be answered without obliterating the very question. Destroy a question with your answer.
–Inspired by Aleksandra Ciric

"Mind that does not stick."
–Zen Master Shoitsu (1202–80)

Superstring theory has revolutionized speculation about the physical world by suggesting that strings play a pivotal role in the universe. Strings, however, always have explained or enriched our lives, from Theseus's escape route from the Labyrinth, to kittens playing with balls of yarn, to the single hair that held the sword above Damocles, to the Old Norse tradition that one's life is a thread woven into a tapestry of fate, to the beautiful sounds of the finely tuned string of a violin, to the children's game of cat's cradle, to the concept of stringing someone along. Use the power of string to explain the biggest or the smallest phenomenon.
–Inspired by Adam Sobolweski

Have you ever walked through the aisles of a warehouse store like Costco or Sam's Club and wondered who would buy a jar of mustard a foot and a half tall? We've bought it, but it didn't stop us from wondering about other things, like absurd eating contests, impulse buys, excess, unimagined uses for mustard, storage, preservatives, notions of bigness…and dozens of other ideas both silly and serious. Write an essay somehow inspired by super-huge mustard.
–Inspired by Katherine Gold

People often think of language as a connector, something that brings people together by helping them share experiences, feelings, ideas, etc. We, however, are interested in how language sets people apart. Start with the peculiarities of your own personal language—the voice you use when speaking most intimately to yourself, the vocabulary that spills out when you're startled, or special phrases and gestures that no one else seems to use or even understand—and tell us how your language makes you unique. You may want to think about subtle riffs or idiosyncrasies based on cadence, rhythm, rhyme, or (mis)pronunciation.
–Inspired by Kimberly Traube

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