College Essays and the Anonymous Reader

Josh Stephens
6 min readDec 6, 2023


You don’t want to wipe out on your college essays.

A student once came to me wanting to write a college essay about her experience learning how to waterski barefoot. Fun, right? She justified this choice on the grounds that it revealed how “unusual” she was.

I couldn’t argue with that. The last time I watched anyone waterski, barefoot or otherwise, was in a Go-Go’s video.

I tried to ask her, though, if readers might interpret anything else from that essay. Something, say… not so flattering. She wasn’t sure.

Therein lies the peril of writing for an unknown audience — consisting of, in this case, college admission officers. Applicants have only the faintest idea who these people are. They have minds of their own and they make their own judgments. Unfortunately for writers who aren’t careful, those judgments can be negative if their writing lacks precision.

Intention and Interpretation
As with the water-skiing student, applicants sometimes focus on what they want their essays to “show” — often a personal quality or moral. They want to “show” leadership through an essay about student government. They want to “show” persistence through an essay about learning ancient Greek; “creativity” through an essay about ceramics; “collaboration” through an essay about the entrepreneurship club; or, indeed, “distinctiveness” though aquatic motorsports.

It’s natural for applicants to want to project appealing attributes like these. But, self-flattery is a perilous proposition, especially when it’s received by people who are not your friends — and when it comes in the form of abstract virtues. In chasing after virtues, applicants often neglect the topics that they are actually writing about — student government, ancient Greek, ceramics, and all the rest. They neglect the topic’s explicit denotations in favor of desired connotations.

As students should know from studying literature, any story — even a nonfictional anecdote — lends itself to many interpretations.

Say a student wants to illustrate “generosity” through an account of volunteering at a homeless shelter. He painstakingly describes his diligence at the ladle, recounting every bowl he filled. He explains how great he feels about dedicating his time to “those less fortunate.” He muses about how glad he is to have traded away hours he otherwise would have spent on Discord or YouTube. In his final sentence, he offhandedly mentions the problem of urban poverty, particularly with respect to rising real estate costs.

As much as he might want to argue that he is Mother Teresa, the critical reader will tell him to get real: there’s nothing in that essay that speaks particularly to the student’s “generosity.” A lot of kids volunteer at homeless shelters, often just to fulfill community service requirements. If he tells himself that “generosity” is paramount, he’s going to miss what could make this essay truly interesting.

He could, instead, be friendly because residents enjoy his company. He could be astute because he’s aware of the greater socioeconomic context of his work. He could be disciplined, because he’s willing to perform a mundane task. Or he could be a walking cliché because literally half the students in urban areas who do community service volunteer at homeless shelters. Maybe he’s actually insincere because, as his activity list might reveal, he’s visited the shelter exactly twice and is trying to make a big deal of it in his essay.

Regardless of the interpretation that the writer wants, reasonable readers can and will reach any of these conclusions, both positive and negative.

Depending on the reader, it might be all of the above, or none of the above. In this case, as in all cases, the writer can rely only on the story he’s telling (about the soup and the residents), the observations he’s making (about life at the shelter), and the ideas he’s presenting (about urban economics). That’s it.

Authors vs. Readers
Writing isn’t just about writing. It’s also about being read. It’s about what an audience thinks about the writer, not about what the writer wants the audience to think about him or her.

Unlike teachers, admissions readers are not just discerning whether writers have constructed a sound argument or understood the course material. Unlike parents, they are not rooting for the writers. Unlike editors, they are not invested in helping the writer make the essay better. Admissions readers have one job: to pass judgment. That judgment can be intellectual, moral, and even aesthetic.

These readers might be scary. But, ambitious writers need to understand their perspectives and respect them nonetheless.

Great essays are, in part, those that are not just flattering, but also those that limit the range of readers’ interpretations. They ensure that, even if readers draw their own conclusions, those conclusions will still be positive.

While writers of course have to maintain their voices and express their convictions, the moment an applicant says, “I want to show my generosity/passion/creativity/leadership/whatever” rather than “I want to tell this particular story because it’s fun…. describe this particular accomplishment because I’m proud of it…. explore this particular idea because it fascinates me…” his essay enters perilous territory.

The literal meaning of the story must come foremost.

If, for instance, a student writes writing about her love of model trains, then she should be proud of loving and knowing about model trains — period. If she wants to emphasize virtues like attention to detail, diligence, fine motor skills, she must do so deliberately and vividly. She needs to describe the fine motor skills through an account of precisely laying track or painting miniature trees and trust that readers will get her drift. Even if they don’t, the writer still has to be proud of trains per se — because, while values are subjective, trains are not.

The Perils of Assertion
If applicants could get into college by simply declaring their own unusualness, leadership, compassion, generosity, curiosity, fine — or fine motor skills — everyone would do it. But it doesn’t work that way.

These proclamations are best described with one of the more useful, but often overlooked, words in the English language: assertion. “Assertion” is another way of saying “just saying stuff,” which is another way of saying “bullsh — ting.”

To put it less profanely, an assertion is a plausible but unverifiable claim. An assertion can be a boast (“my leadership helped the robotics team win”), an empty supposition (“the bake sale really brought the class together”), or a mindless exaggeration (“I discovered my passion for history when I saw Bill and Ted’s Excellent Adventure”). Writers often rely on assertions because they are trying to say nice things about themselves. What they don’t understand is that detached readers, who don’t know their applicants and have no a priori reason to like their applicants, have not the slightest reason to believe their assertions.

The Dude put it best: an assertion is, “just, like, your opinion, man.” And, man, readers are never required to agree with your opinion.

Applicants who really helped the robotics team win, really held a great bake sale, or really love history should try to convey detailed, authoritative accounts of robotics, bake sales, and history. The details — not the assertions — will win over those anonymous, judgmental readers.

All of this brings me back to barefoot water-skiing.

Think about all the connotations of water skiing (barefoot or otherwise) about how they might reflect on the student. Is “unusual” the first thing that comes to mind? If it is, is it the type of “unusual” that is admirable? Think about how water-skiing relates to colleges that are seeking smart, active, personable, mature — and, yes, creative and quirky — students to join their community.

Unless the college has a large, underutilized lake on campus, that topic is more likely to sink than swim.

Josh Stephens is a longtime educator based in Los Angeles. He has advised domestic and international students on college applications for over a decade. He blogs about college admissions and essay-writing on Medium and the Huffington Post. He earned his bachelor’s degree in English at Princeton University and his Master of Public Policy at the Harvard University Kennedy School of Government. He is the author of the recently published book The Urban Mystique. He can be reached at

Image courtesy of Paul Pehrson via Flickr.



Josh Stephens

Josh Stephens is a veteran teacher and college counselor based in Los Angeles. Josh can be reached at