Picking the Locks

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by CARA FEINBERG

The fall of my senior year of high school, I spent a very long time not writing my Big College Essay. It was a project I was already supposed to know how to do — two pages with just one job: to capture, in entirety, who I was. Oh, and it should hint at a keen intellect. And a social conscience. And a couple acts of heroism.

Two weeks before the deadline, after a weekend of jittery panic spent in my family’s computer room, I brought my essay to a trusted teacher. He read it while I sat on the other side of his desk, and when he finished, he folded the paper over and handed it back to me, shaking his head. “This is terrible,” he said. “Now let’s fix it.”

As clearly as I remember the agony of those months before that meeting, I also remember the relief that swept in afterward. The turning point came not with the word fix, but with the word Let’s. Suddenly, there was a “We,” another person in this with me who thought I had something important to say, and who, without any of the anxiety I brought to the project, seemed to know that somewhere in me, somewhere not yet on the page, there was a better story. A truer story.

These days, when I am not at Hillside, I make my living as a professional writer and documentary producer. I can’t say I’ve completely avoided the Blank-Screen Torture Chamber, but I have learned how to pick the locks to escape. I often begin by asking myself questions my high school teacher asked me in the “Let’s fix it” stage:

Am I, as the author, interested in what I’ve written? (“If you don’t want to write this,” my teacher had said, “why should I want to read it?”).

What makes this story mine? (“Tell me a detail I cannot already imagine,” he said.)

Why have I chosen to tell this particular story? (“Tell me how you feel now compared to how you felt before this happened.”)

I credit my teacher not only for rescuing me in my confrontation with my college essay, but also for giving me tools that I now use both as a journalist and in my work at Hillside. As an interviewer and a writing coach, I try to do for others what my teacher did for me: to make people comfortable in speaking openly with me; to listen in a way that helps them recognize the best details of their stories; and to discover with them how their stories became theirs. As a journalist, I have to weave together the story threads on my own, but as a coach, I get to be part of the “We,” the member of the team who asks the questions to uncover the details that inspire the writing. It’s rewarding work, as a writer, a reader, and a human. I value it in part because I remember how it felt to be in the Torture Chamber, but mostly because I remember the relief of hearing the word Let’s — how it felt to begin again, with a coach on the sidelines, and to see a story emerge, draft after draft, that wasn’t My Big College Essay but my essay.

The Illuminating Incident in the College Essay

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by KATE LEARY

In her book The Writing of Fiction, published in 1925, Edith Wharton coined a phrase that’s useful to the college-application essay writer as well as to the novelist.

At every stage in the progress of his tale the novelist must rely on what may be called the illuminating incident to reveal and emphasize the inner meaning of each situation. Illuminating incidents are the magic casements of fiction, its vistas on infinity.

When I read Wharton’s pronouncement, I felt its rightness. I’m at work on a novel, and I knew the concept of illuminating incidents could help me pull back and evaluate each scene I’ve written. Yet Wharton’s high expectations intimidated me. If I sat down to draft with her words at the forefront of my mind, fixated on “inner meaning,” I would freeze. I thought about my Hillside clients, who are tasked with writing 650-word essays that convey their authentic selves. They’re searching for inner meaning, too. The assignment can feel unbearably intimidating.

Wharton emphasizes the importance of choice — “the disengaging of crucial moments from the welter of existence.” And this is precisely how the Hillside process begins, in conversation exploring moments that clients have already identified and begun to open in our preliminary exercise, Ten Sentences. Clients needn’t come to the first session knowing why they chose those moments. Lively conversation brings context to the moments and often uncovers new ones; gradually, coach and client discover together which experiences hold meaning, and which seem to speak to each other. Both client and coach feel when they’ve struck a rich vein — a crucial moment. When I started coaching, I worried that it would be hard to tell when the student and I had arrived at one, but a palpable energy tends to enter the conversation, sometimes so obvious that we both laugh.

I’ve had a lot of practice at writing, and yet I can still struggle to get started, just like many college applicants. Sometimes when I want to try something new, my ideas and ambitions feel so big that it’s a challenge even to write a first sentence. Wharton offers practical advice for this problem:

The only remedy is absolutely to abandon the larger for the smaller field, to narrow one’s vision to one’s pencil, and do the small thing closely and deeply rather than the big thing loosely and superficially.

Here, again, is the essence of (and the instruction in) the Ten Sentences exercise. For the Hillside client, doing the small thing closely and deeply at the start of the process leads naturally to doing it at the start of the essay — drafting that crucial moment with attentiveness to detail. I prompt clients to describe how the scene looked through their eyes, what physical sensations they had, what sounds they heard, what feelings arose in the moment. This is Wharton’s remedy, and college admissions officers consistently give advice that sounds remarkably similar. One Tufts admissions officer writes: “As I see it, you have two options when exploring a topic in your college essay: go broad or go deep.” Her strong preference? Go deep. “By focusing on details, you set yourself apart.”

The conversation doesn’t end when drafting begins. It grows only more interesting as the student and I examine and question the details together, building connections. Eventually, the crucial moment becomes an illuminating incident, revealing something the student considers significant about her authentic self. I won’t pretend to understand everything about how this happens. Wharton’s description of illuminating incidents as “magic casements” feels appropriately evocative and mysterious. I’m regularly surprised by what clients discover about themselves in the act of writing and revising. I remember these discoveries because I vividly recall the scenes my clients have worked to recreate on the page. I remember the feeling their scenes gave me — of peering in a window to some previously unseen (sometimes previously unrecognized) part of the person. In Wharton’s words, “these scenes shed a circle of light far beyond the incident recorded.” Inspired by my clients’ work, I aim for the same in my novel writing.

The Essayist's Real Challenge

by ALLAN REEDER

In supporting college applicants' thinking, imagining, and writing, we at Hillside are often demonstrating why concern about what an essay is "about" must not precede close interest in and examination of the raw material — close looking at the specific details of experience. Don't rush to meaning! A fresher, truer "aboutness" almost invariably results from patient recollection (indeed, re-collection) and consideration. 

And so when To Write a Great Essay, Think and Care Deeply, from The Atlantic's By Heart series, came to our attention, we applauded. In appreciation for the lessons he finds in J.R. Ackerly's My Dog Tulip, nonfiction writer Lucas Mann describes Ackerly as "leaning closer, looking so carefully" and notes that "it’s the closeness in his gaze, his dedication to looking, that transforms the subject." Mann reflects how we tend to "prioritize a weighty topic over the force of an author’s gaze, the clarity of her prose, the sincerity of her emotion." He goes on: "[I]t’s important for me to remind myself sometimes that, at its heart, that’s all a great essay is: a virtuoso performance of care." 

Frequently we talk at Hillside about how the interesting writer is the interested writer — how just isolating and describing the specifics of experience with careful attention (attention that is full of care) is not only an essential step in realizing an authentic meaning but an engaging act in itself. As Mann writes, "[S]pending one’s time fretting about aboutness is a deflection from the essayist’s real challenge: to think and feel as deeply and specifically as possible about whatever it is you’re looking at."