How To Ace Your Supplemental Essays



Supplemental essays are personal statements. They need to be about you, tell a compelling story, and so on. I know, I know—you’ve already written a personal statement, and now you’re being asked to do so again, over and over. It should go without saying that you can’t reiterate anything you’ve already said in your Common App. So how should you approach the supplemental essays?

Supplemental essay prompts can be “general” (open-ended questions about what inspires you and so on) and “specific” questions. (The University of Chicago has a ton of quirky options: "what can be divided by zero?", "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)". etc.)

Here are some strategies for approaching both general and quirky questions. I’ll also take a look at the ubiquitous “why this college?” question, as well as the “community” question.

General questions

The good news is that, for “general questions,” you can usually kill two or more birds with one stone. Take a look at all your supplemental essay prompts side-by-side and spend some time strategizing. This year, Yale has a supplemental question that goes:

Yale’s extensive course offerings and vibrant conversations beyond the classroom encourage students to follow their developing intellectual interests wherever they lead. Tell us about your engagement with a topic or idea that excites you. Why are you drawn to it?

One suggestion for a Harvard optional supplemental (more on optional essays later) reads:

“An intellectual experience that has meant the most to you.”

Same question.

Now take a look at a Princeton prompt:

“Culture is what presents us with the kinds of valuable things that can fill a life. And insofar as we can recognize the value in those things and make them part of our lives, our lives are meaningful.”

If you can write about an intellectual idea/experience that is also cultural in nature, you’ve got three essays for the price of one. Maybe you’re into post-WWI European avant-garde art movements? Take a look at the other questions for these three universities: there are other overlapping questions that may inspire you more than intellectual ideas and culture.

You’ll need to keep word-count in mind: Yale wants 250 words or fewer, Princeton asks for “about 500,” Harvard doesn’t say (probably best to aim for around 500 words). Write the longer version first, and then whittle your essay down for Yale.

Quirky questions

Have some fun, and most importantly, be yourself. In your U Chicago response to "What can actually be divided by zero?", for instance, not only do you have to come up with a response, you first need to decide what the question means. If this was just about mathematics, the answer would be fairly simple. How else could you interpret the word “division”? How else could you interpret “zero”? Make sure you pick something the reader can get on board with. Too far out of the box, and you’ll lose the reader’s trust from the start.


Even just setting up your response will be a challenge here. You want to communicate your understanding of the question without repeating it. Ideally, you want to imply your interpretation by the clarity and focus of your answer. This is no easy feat though in response to such a vague prompt.


It’s harder to recycle essays for quirky topics, but sometimes you get lucky. Let’s say you wrote about your interest in mathematics for your Yale/Harvard/Princeton essays. For Chicago, you can possibly recycle elements from your Yale, Harvard, or Princeton essays.

“Why this college”

There are no shortcuts here. You can’t turn in your essay for College X to College Y just by changing the name. Just as you should be the only person on earth who could have written your personal statements, your response to the “why this college” prompt should describe College X in such a way that only College X will recognize itself in the picture you paint. Do your research. Discuss the classes you visited, the atmosphere on campus, the clubs you’d like to join, and so on.

Sometimes colleges try to personalize this question by telling you something about who they think they are. Tufts asks:

Which aspects of the Tufts undergraduate experience prompt your application? In short, "Why Tufts?"

It’s like the university is saying “hint, hint!” when it calls its community “intellectually playful.” You may have plenty of “serious” things to say about your interest in the School of Engineering—that’s fine. Don’t feel the need to write an essay that’s all about playfulness (whatever exactly that means) just because it’s in the prompt. Rather, take the mention of playfulness as an indication that it’s OK to show your quirky side, assuming it relates to your interest in Tufts.

Community and diversity

Essays that ask about the communities you belong to (related to your upbringing, your religion, your ethnicity, your sexual orientation, your gender, and so on) can be tricky, regardless of your background. Even if you have an incredible story to tell (such as one that relates to facing real discrimination), it’s not enough simply to explain to admissions folks that you’ve overcome adversity. You also need to show how your experiences have shaped who you—and only you—are today. As always, make sure that your story is yours alone. Don’t fall into the trap of telling the tale of an entire community: if being a Mormon in New York City isn’t always easy, don’t stop there—talk about your own experience, and how it informs your unique personality.

A message to all the cisgendered, able-bodied, agnostic, middle-class white guys out there: if you haven’t given much thought to what diversity means, now’s a good time. A diverse community is not a community without folks like you. Don’t try to marginalize yourself if you’ve never had the experience of being marginalized, but do focus on what makes your background unique. I’ve seen excellent essays about being from Wyoming, attending a high school with a graduating class of eight, being a military brat, helping out at the family-owned bar as a child, or catching flack for being a boy who likes ballet. We all have different backgrounds. The point of this essay is to see whether you’re self-aware enough to recognize that, to see if you can imagine how your unique experiences will benefit a diverse community.

Optional essays

The question, of course, is whether these questions are really optional.

The simple answer is, not really, despite what the colleges who ask them say. You probably suspected as much.

One notable exception to this rule comes to mind. Some optional essays are specifically designed for certain applicants. Duke, for example, proposes the following optional essay prompt:

“Duke’s commitment to diversity and inclusion includes sexual orientation, gender identity and gender expression. If you would like to share with us more about how you identify as LGBTQIA+, and have not done so elsewhere in the application, we invite you to do so here.”

It goes without saying that, unlike the general “community” question, this prompt is not an opportunity for just anyone to chime in and benefit from additional space in the application. If you do not identify as part of the LGBTQIA+ community, sit this one out.

#collegeapplication #collegeessays #highschool

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