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Articles / Applying to College / College Essay Challenges

College Essay Challenges

Dave Berry
Written by Dave Berry | Feb. 2, 2016

Let’s talk about college application essays, especially challenging essays. This information is for high school juniors who will be facing some of these this fall. It’s never too early to start thinking about your application essay strategy.

“Challenging” can also be considered “weird” or “unconventional.” My personal opinion about these types of essays is that colleges have grown tired of reading the same kinds of boring essay responses over past years and are looking for entertaining and insightful responses from their applicants.

Also, I think colleges are looking for original thinkers, young people who have a “voice” that they can express in an intriguing writing style. I would have loved to have had the chance to respond to some of the more unconventional essay prompts that have appeared recently. Of course, the University of Chicago is famous for its offbeat essay prompts. Consider these:

– Orange is the new black, fifty’s the new thirty, comedy is the new rock ‘n’ roll, ____ is the new ____. What’s in, what’s out, and why is it being replaced?

– “I learned to make my mind large, as the universe is large, so that there is room for paradoxes.” –Maxine Hong Kingston. What paradoxes do you live with?

– 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.

– “Art is either plagiarism or revolution.” –Paul Gauguin. What is your “art”? Is it plagiarism or revolution?

– Rerhceseras say it’s siltl plisbsoe to raed txet wtih olny the frist and lsat ltteres in palce. This is beaucse the hamun mnid can fnid oderr in dorsdier. Give us your best example of finding order in disorder. (For your reader’s sake, please use full sentences with conventional spelling).


When I see the word “paradox,” I think of two physicians. That may give you an insight into how I think. Don’t cringe. Humor (even marginal humor) is a key element in dealing with application essays and I’m sure that the readers at UChicago welcome an opportunity to laugh. Keep in mind one of my essay maxims: “Make an admissions officer smile and you’re halfway home.”

The University of Chicago is not the only school to challenge applicants with its essay prompts. Here are a few others:

– Write a haiku, limerick, or short poem that best represents you. [New York University]

– Are we alone? [Tufts University]

– If any of these three inanimate objects could talk, how would your room, computer or car describe you? [Haas School of Business at UC Berkeley]

– Can a toad hear? Prove it. [Bennington College]

– If you were reduced to living on a flat plane, what would be your greatest problems? Opportunities? [Hamilton College]

– In the year 2050, a movie is being made of your life. Please tell us the name of your movie and briefly summarize the story line. [New York University]

– Write a short story using one of the following titles:

  • House of Cards
  • The Poor Sport
  • Drama at the Prom
  • Election Night, 2044
  • The Getaway

[Tufts University]

– Sartre said, “Hell is other people”; but Streisand sang, “People who need people / Are the luckiest people in the world.” With whom do you agree and why? Don’t be icky. [Amherst College]

How’s your imagination? Do you have a sense of humor? Do words flow easily from your keyboard or pen?

In all my years of helping college applicants deal with essays, the one persistent error that has infected their approach to unusual essay prompts is the inability to speak with original authority. Many write what they think the admissions officers want to hear. That’s just flat out wrong. The key is to write what you want to say!

Writing from a position of authoritative, original strength is a tremendous advantage, as it applies to application essays. In most cases, the person reading your essay responses will never have met you. Thus, your words will paint your portrait for them. You want that portrait to be a dramatic fresco, not a timid miniature. So, how do you do that?

Allow me to pick one of the above prompts and show you how I would, in part, approach it. Let’s go with Amherst’s Sartre said, “Hell is other people”; but Streisand sang, “People who need people / Are the luckiest people in the world.” With whom do you agree and why? Don’t be icky.

I would first attack the term “icky.” Something like:

“If by icky, you mean sentimental, then don’t worry. Yeah, I may not watch movies or TV shows that feature animals because I can’t stand the thought of them being exposed to potential harm, but when it comes to people, I’m a total hard-bottomed, unsentimental objectivist.” …

That approach should grab your reader’s attention. Now on to some finer points.

“Sartre hits the nail dead center. He also alludes to the contrast in personality types. Obviously, Sartre was a big introvert. I speak with authority about that because my Myers-Briggs Type Indicator preference score for introversion is off the charts.

“I love solitude, quietude, repose, reflection, and pondering. Just shut off that stupid TV, with all its mindless jabbering, stentorian commercials, and bad news! Put on some late Brahms piano pieces, especially the Intermezzo Opus 118, No. 2 in A Major. And while you’re at it, go get your own chicken breasts at the Walmart Supercenter …”

Getting the feel for an original, “authoritative” voice?

After some further specifics to support my Sartre sympathies, I would have to address Streisand:

“… My own version of Streisand’s lyrics might go something like, ‘People who need people are the most dependent people in the world.’ Our world is just way too needy. Where’s the spirit of independence, fortitude, individualism, and bootstrap-pulling-up determination? Huh? Sure, let’s help the less fortunate among us and have compassion where needed, but for the love of all things sacred, let’s quit enabling those who would take advantage of us!

“I would love to have seen Sartre in an encounter group, sharing his “feelings” with those around him. I’m thinking of Mad Men‘s Don Draper in the series finale. He was the world’s biggest square peg in a touchy-feely round hole. Yeah, he did come up with that catchy ‘I’d like to buy the world a Coke’ commercial, but he had to endure Sartre’s ‘hell’ of people before he uncorked (unCoked?) it …”


Anyway, you can finish my draft for me. I hope you also can see how being original and authoritative can be a big advantage in dealing with essay challenges. That’s why colleges invent these unorthodox prompts. They are trying to get you to drop your mask and your inhibitions. It’s kind of like going to a party where you know no one.

Here’s the analogy: The people at the party are the admissions officers and you, as a guest, are the applicant. Your application is your “visage.” You can attract or repel others by the way you “look” (write).

If things go well, and you project an interesting and compelling aura, by the end of the evening, you will have made a few new friends (advocates on the admissions committee), and you’ll be invited back to another party down the road (probably getting that fat envelope or email). You may not believe me about this, but I’ve seen it work time after time.

Be who you are, not what you think they want you to be. This is probably the surest method of all in finding the right fit for your ideal college. So, think about that between now and October. You’ll be glad you did.


Be sure to check out all my college-related articles at College Confidential.

Written by

Dave Berry

Dave Berry

Dave is co-founder of College Confidential and College Karma Consulting, co-author of America's Elite Colleges: The Smart Buyer's Guide to the Ivy League and Other Top Schools, and has over 30 years of experience helping high schoolers gain admission to Ivy League and other ultra-selective schools. He is an expert in the areas application strategies, stats evaluation, college matching, student profile marketing, essays, personality and temperament assessments and web-based admissions counseling. Dave is a graduate of The Pennsylvania State University and has won national awards for his writing on higher education issues, marketing campaigns and communications programs. He brings this expertise to the discipline of college admissions and his role as a student advocate. His College Quest newspaper page won the Newspaper Association of America's Program Excellence Award, the Pennsylvania Newspaper Publisher's Association Newspapers in Education Award, the Thomson Newspapers President's Award for Marketing Excellence and the Inland Press Association-University of Kentucky School of Journalism and Mass Communications Inland Innovation Award for the Best New Page. His pioneering journalism program for teenagers, PRO-TEENS, also received national media attention. In addition, Dave won the Newspaper Association of America's Program Excellence Award for Celebrate Diversity!, a program teaching junior high school students about issues of tolerance. His College Knowledge question-and-answer columns have been published in newspapers throughout the United States. Dave loves Corvettes, classical music, computers, and miniature dachshunds. He and his wife Sharon have a daughter, son and four grandchildren.

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