The Uncommon Essay

Discovery Process + 4 Private Sessions + Final Feedback

What’s The Uncommon Essay Course?

The Uncommon Essay Course is our most comprehensive, instructive support for writing the main application essay. We developed this unique one-on-one process from our years of studying students’ obstacles, turning points, and insights in the progression from personal story to self-reflection.


Is The Uncommon Essay Course Right for Me?

If you have not yet written your essay and are looking to explore your experiences, discover your truths, establish a writing vision, and draft with direction, the course is for you! On the way to your final draft, you will learn from your coach about writing from your authentic voice with imagination and precision. The launching Discovery steps will also equip you with material to consider when it’s time to turn to college-specific supplement essays.

How Does the Course Work?



In a 15-minute video meeting with the coach, student and parent(s) learn about the course and are launched in Discovery steps.

The Ten Sentences Exercise

The essay-writer receives online access to Hillside’s Ten Sentences Exercise, our instructive, motivating method for gathering distinct experiences and beginning to identify possibilities and opportunities.

Two Cents From ‘Rents

While the writer gathers Ten Sentences, parents — a rich source for perspectives on a student’s experiences — respond to a set of reflective questions.

The Ten Sentences Exchange

From study of the writer’s Ten Sentences and the Two Cents responses, the Hillside coach gets curious and designs a written online exchange with the writer about promising material, uncovering pivotal details and reflections for exploration in Session One.

Coaching Sessions

Session One: Exploration & Direction

Discovery continues through energetic conversation that reveals ways forward. After the session, the coach sends the writer a recap, reinforcing significant findings and detailing the initial writing assignment. The parent is copied.

Session Two: Story, Prompt, & Structure

The coach and student collaborate in building the essay roadmap in a shared online drafting doc. Considering story details and reflective opportunities, the coach teaches about essay structure. The student will write an initial draft of the essay before Session Three.

“I think students would be surprised to know that admissions officers aren’t looking for anything exotic. The more specific examples you can use, the more you can make it a story with very specific details, the better. The essay should make the admissions officers feel like they’ve had a conversation with you and want to learn more.” Yale University admissions officer

Session Three: Intensive Draft Review I

Reading the first draft out loud launches top-to-bottom revision work, locating areas for clarification and further reflection. Prompted by notes made during the session, the writer will prepare a complete second draft before Session Four.

Session Four: Intensive Draft Review II

Another patient out-loud review of the essay focuses on trimming and sharpening. Revision progresses with plenty of sentence-based instruction! From session notes, the writer will prepare a complete third draft for the coach’s final review. The writer also receives Hillside’s guide to addressing the most common supplement-essay prompt. The coach emails the parent with an update on the student’s progress following this session.

Final Feedback

Final Feedback (1 hour)

The student sends the coach the latest revision by an agreed-upon date, and within a week the coach delivers electronic feedback to help the writer reach the final draft.

A student’s initiative, focus, perseverance, and writing ability are factors in how efficient the writing process is. Students requiring support beyond the standard structures may extend work with their coach through Feedback Sessions or E-Feedback.

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What Clients Are Writing About The Uncommon Essay

This has been a high point of our son's high school education. The moment we knew it was a triumph was when he came out a college interview feeling sure that the Hillside coaching had put him in the position of saying, clearly and in a way he believed in, what matters to him about his education.
Parent, Crozet, VA
Thanks for creating such a thoughtful, caring service for self-discovery and expression for young adults. I wish I had this when I was my daughter's age!
Parent, San Franciso, CA
Honestly, this process has been so good for my son. He's mentioned many times how much he's learning. No matter the outcome of the college process, I know he's gained a lot from this part of it!
Parent, Newton, MA
We have appreciated your support so much over the years. With patience, positivity, and process, you bring out the best in kids so they can share their stories!
Parent, Wellesley, MA