What’s The WayFinder?

This is our exploratory program for students seeking to identify and investigate their most promising stories for college applications — and to get writing!


Is The WayFinder Right for Me?

If you’re uncertain about what story you have to share with colleges, The WayFinder will help you to gather your experiences and to discover in them distinct opportunities for writing your main application essay. Your coach will teach you ways of seeing and thinking that will get you started with direction. The WayFinder does not include planning the essay structure or receiving feedback on drafting. If you’re seeking more comprehensive support, you can consider The Uncommon Essay Course or add further support later.

The WayFinder is appropriate if you’re a rising senior applying to college this year, but it’s also good preparation if you’re applying to college next year.

How Does The WayFinder Work?


Orientation Meeting

In a 30-minute meeting, the student and parent(s) learn from the coach about the exploratory path ahead and get started with Discovery steps. Parents are not required to attend but are welcome.

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 coach gets curious and designs a written online exchange with the writer about promising material, uncovering pivotal details and reflections for exploration in the coaching session.

Describing a single experience or interaction or memory or source of inspiration with vivid detail and deep reflection can often have the most powerful and original impact. Tufts University admissions officer

Coaching Session

Coaching Session

The coach plans and leads a one-hour session of energetic conversation that opens up and investigates select experiences highlighted in the Exchange. By isolating details and prompting reflection, the coach helps the student to sharpen their vision of possibilities for drafting. This session is for the student and the coach only.

photo of map with pins in it


Findings & Recommendations

Following the session, the coach prepares Findings & Recommendations for delivery to both student and parent. This includes a distillation of session notes, the coach’s perspective on discoveries and opportunities, and a customized writing prompt to help the student begin the writing process. Coaches may choose from a variety of tools — Google Docs, video, and audio — to convey their findings.

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Options for Further Support

Following The WayFinder, a student may seek feedback on drafting through individual Draft Feedback Sessions or E-Feedback (coach’s schedule permitting).

What Clients Are Saying About The WayFinder

The coaching couldn’t have been better. Once I got everything out on the table, you helped me see what would work best. Your questions were just enough of a push to look further than I could have on my own. And once I had said it, I was able to see it.
Student, Pasedena, CA
Hillside uses a completely individualized approach, encouraging the student to find a topic that has personal meaning. This made the writing less onerous because the topic was always authentic and relevant to who my daughter is as a young person and as a college applicant.
Parent, Providence, RI