College Application Essays: 3 Tips for Mastering Supplemental Essays

Girl at her laptop

College Application Essays: 3 Tips for Mastering Supplemental Essays

Meet our College Essay Coach

College Essay Coach and English Teacher Chris Cullen

Hi, my name is Chris Cullen. I’ve taught English and worked as an essay coach at MEK for the past two years and have been a professional writer for the past fifteen.

My connection to the written word forms the core of my soul. On the advice of William Faulkner, I “read everything,” but I have a predilection for the novels of John Steinbeck and the short stories of F. Scott Fitzgerald, Jack London, and Edgar Allan Poe. I’m also an avid cinephile who worships directors like Oliver Stone and Martin Scorsese, a music lover whose tastes straddle the line between hard rock and electronica, a lifelong and at times unfortunate fan of the once dominant Miami Dolphins, and an enthusiastic home cook who likes nothing more than to create dishes from found ingredients in the fridge. Mostly, I enjoy laughing deliriously with my wife at things we only understand.

This is a glimpse of my world, but it’s being granted access to the worlds of my students, being offered a window into their experiences and passions, that provides me with the utmost joy. All students have illuminating stories to tell, and it’s an invaluable privilege for me to help those students discover, shape, and unleash their stories onto the outside world.

Supplemental Essays

So, you’ve just finished your opus—the final draft of your Common App—and are now ready to tackle the monster that is college supplemental essays.

Where do you begin?

Therein lies the rub.

For this important and sometimes daunting aspect of the college application process, I’ve come up with a simple three-step model to follow—the three R’s, if you will—that will offer you insight into the different types of supplemental essay prompts and the difficulties of each.


The Last of the Mohicans Poster

What would Daniel Day-Lewis do?

The three-time Academy Award-winning English method actor Daniel Day-Lewis has earned as much reverence for his legendary preparation as he has for his staggering talent. For example, to get in the headspace of his survivalist protagonist Hawkeye for the 1992 historical epic The Last of the Mohicans (1992), he eschewed all modern technology and lived in the wilderness for months, during which he learned how to track and skin animals, build canoes, and fight with eighteenth-century weapons. (Tomahawks, anyone?)

Now, I’m not expecting you to go all Day-Lewis on us and become a “method researcher”—though that is an interesting concept—but the college application process should be an immersive experience, one that involves more than cursory perusals of a college’s website. Day-Lewis made his roles count, and you should also make the schools you apply to count, whether it’s six schools or twenty.

Supplemental essay prompts are unique in the fact that many colleges have their own. These prompts come in all shapes and sizes—ranging anywhere from 1 to 500 words—and can change from year to year depending on the school. So, once you have your college list finalized, I recommend that you start regularly checking application websites this summer for the most up-to-date prompts, all of which are typically released by September 1st.

One supplemental essay you will assuredly encounter is the “Why X School?” prompt, which appears in several different iterations—ones that, at their core, are nonetheless all the same. A good starting point for this one is the respective school’s website, which will allow you to glean pertinent information about academic and study abroad programs, student life, clubs and extracurricular activities, and faculty members in your major of choice, among other things. If you’ve visited the school, you should also most certainly draw from personal experiences and observations, which will help give your essay an added one-of-a-kind touch.  

Ultimately, through research, you want to uncover unique aspects of the school that speak directly to your personality and interests. Why are you a good fit for this school? That’s the main question you should be answering here. Please, please, at all costs, avoid insincere praise and generalizations (“As one of the most prestigious institutions in the world, Harvard is…”), otherwise you’re just wasting words. You want to be genuine, of course, but never fawning and, even worse, boring. You want to be a step above and ahead of the rest, and like that Day-Lewis fella, uber-prepared.

Step #2: REPERTOIRE        

History of the Eagles Cover

It’s all about repertoire.

In the compulsively watchable two-part documentary History of the Eagles (2013), about the seminal American rock group the Eagles, singer Jackson Browne recalls enjoying one of the band’s 1994 reunion shows alongside actor Jack Nicholson, who at one point simply turned to him, and said, elatedly, in his classic raspy voice: “Repertoire.”

In one word, Nicholson summed up the Eagles’ legacy as one of the greatest rock bands of all time. Point is, what’s in your repertoire? What are your skills, qualities, and quirks, and how have you channeled them into action? Have they already crystallized into desires and future goals? These supplemental questions are your time to reflect on your every facet, attribute, and achievement, and to present what I like to call a kaleidoscopic representation of your soul.

Such reflections, however, shouldn’t be limited to, say, how many competitions you’ve won. Yes, these are great and possibly worth mentioning at some point. But, more importantly, colleges want to know how your mind works, as in, if you were to mash up a historical figure with a new time period, environment, location, or occupation, how would you tell his or her story? If you were to teach a college course, what would it be called? If you were to write a letter to your future roommate, what would you want to reveal about yourself?

Those last three questions in the above paragraph are, in fact, paraphrases of actual supplemental essay prompts, for the University of Chicago, Yale, and Stanford, respectively. Unlike the more common and popular question types, these creative prompts require some serious out-of-the-box thinking. Welcome this opportunity. But don’t try to be too clever for your own good (i.e. rambling stream-of-consciousness musings). You must always continue to be true to yourself, and there’s a way to do that while still being memorable to admissions officers. So let the self-discovery begin, and unveil to the world those thoughts and ideas that come to you at three o’clock in the morning when you can’t sleep due to the uncontrollable fire that is burning inside of you. Because that’s part of your repertoire too, you know.


Renowned Spanish chef Ferran Adrià, often hailed as the godfather of molecular cuisine, pioneered the use of avant-garde cooking techniques to deconstruct familiar dishes and foods. One of his most famous culinary innovations includes liquid olives, in which olive juice is made to look like real olives through a spherification process involving several unusual ingredients. The solid spheres immediately dissolve upon ingestion, creating an explosion of pure olive essence. (I’ve had these at a restaurant helmed by one of Adrià’s proteges, and they’re mind-blowingly good!)

Release your essence.

Adrià’s deconstructivist approach to cooking is not unlike the revision process in writing, which requires you to cut out the filler and pare words down to their essence. Let’s face it, when you’re charged with responding to supplemental prompts with strict word counts, you have absolutely no room for extraneous bits. Some selective schools like Princeton, for instance, even require applicants to respond to super short answer questions like, what is your favorite source of inspiration? Or what are two adjectives your friends would use to describe you? My main advice for these types of questions is to keep it light and unpretentious. Trying to find the perfect words for these is a futile endeavor.   

All told, revision, irrespective of supplemental essay type, is a step that should not be overlooked in anything you put pen to paper for, as the best writing—as countless scribes have said before me—is always achieved by rewriting. I’m emphasizing this here because I’ve sometimes seen students hit a wall once they begin writing their supplemental essays due to burnout. And when said essays feel like a chore, their quality will inevitably suffer, which you never want to happen. All applications are reviewed as collective portfolios, so you don’t want to follow a strong Common App essay with lackluster supplemental responses. You need to tackle the latter, like everything else, with a single-minded focus and purpose. That said, follow Adrià’s lead and start chipping away at your true essence, one word at a time.

(As a fun self-exploration exercise, go to the first paragraph of this blog post and use as a model to write a 150-paragraph about yourself, one that captures the essence of “you” in all your glory. Yes, every word in that paragraph is shamelessly deliberate.)

Getting Started

All of us have stories that are worth telling, but more often than not, we need direction when telling them. This is where MEK comes in.

If you want expert guidance on crafting strong college application essays from start to finish, sign up to work one-on-one with me or one of my fellow expert essay coaches through our Application Essay Writing Program.

You can call 855-346-1410 or contact us here to get started!

Chris Cullen

Chris has worked as a professional writer for over a decade and has applied invaluable real-life skills learned in the media and publishing industries to his work as a teacher. His easygoing demeanor, thoughtful nature, and strong passion for writing work in concert to help students gain a newfound appreciation for the written word.


Don’t miss the next insider event.


Looking for an ACT Program? Click Here