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Leave the Story Open (and the Window Closed)

The first thing she saw was the open kitchen cupboards. Then she heard a crunch underfoot. She looked up and saw the window — which opened onto a fire escape — ajar. And she knew, with a shiver, that she had a problem.

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Give Yourself Away

As a young writer, I often felt I needed to write about something beyond myself — something accessible only to writers older, more intelligent, more talented than I was. This pressure often resulted in stagnant, dreadful writing, full of clichés.

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Picking the Locks

The fall of my senior year, 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.

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The Illuminating Incident in the College Essay

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.

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The Essayist’s Real Challenge

Don't rush to meaning! A fresher, truer "aboutness" invariably results from patient recollection. And so when "To Write a Great Essay, Think and Care Deeply" appeared in The Atlantic, we applauded.

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The Comedian and The College Applicant | Part Two

Every joke depends on sentence design. Just as a stand-up onstage is alert to the structure and style of delivery, I listen with students to their original ten sentences.

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The Comedian and the College Applicant | Part One

After learning of the delight I take in exploring the evolution of a good sentence, a friend sent me “A Stand-Up Joke is Born" from the New York Times. I didn't expect to see so many parallels between the way comedians work on a joke and the process I've developed at Hillside.

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