At the boarding school where I work, our four college counselors guide 123 seniors through one of the most challenging parts of the college application process: the personal essay. The challenge is a new one for many of our students. Everyone wears coats and ties. They follow rules. They naturally want to fit in. One girl gets a pair of shoes, and suddenly everyone's wearing the same thing. It's an environment that fosters academics and relationships, but it can make self-expression feel risky. The college essay demands the opposite: authenticity, individuality, vulnerability. How do we help students in this environment learn to express their authentic selves?

My approach is a year-long, structured essay process that builds students’ confidence through continuous support. Strong college essays require time, partnership, and the freedom to develop ideas without the pressure of the October deadline.

Planting Seeds in May

Our process begins long before most students are thinking about college deadlines. After AP exams in May, we still have a few weeks of classes, and this is when I partner with our English department to start talking about the writing students will need to do for their college application. The strategic framing matters: We call it a “personal narrative” rather than an intimidating “college essay.”

Teachers provide initial feedback in class during those final weeks. We introduce the Common Application's seven prompts to get students started brainstorming. Over the summer, students send me drafts, and we ping-pong back and forth virtually. Sometimes I'll hop on a call if a student needs to talk through their ideas, but most of the work happens asynchronously.

The goal over the summer isn't perfection; it's momentum. When fall arrives with its cascade of deadlines, students aren't starting from scratch. They're revising, refining, and polishing work they've been developing for months.

The Honest Feedback Challenge

One of the hardest parts of my job is delivering honest feedback. In a boarding school, relationships matter deeply, and students come to your office not just for college counseling but for support through a stressful process.

Sometimes an essay just isn't working, and saying so directly can feel crushing to a student who's already anxious. I spend a lot of time trying to be both honest and encouraging, but students need to hear the truth if they're going to improve their writing before deadlines hit. Like many counselors, I'm experimenting with new approaches to this challenge. Some colleagues have students workshop essays in peer groups. Others bring in outside readers for fresh perspectives.

In guiding my son and his friends through their college essay process, technology has complemented my work, but it can’t replace the relationships I build over time. No tool can fully account for a student’s self-confidence, personal loss, or the challenges of being the first in their family to apply to college. That context shapes how I deliver feedback and support.

I’ve also explored structured, tool-based feedback on platforms like Esslo as a way to add a separate, lower-pressure viewpoint alongside my own comments. Used thoughtfully, feedback that isn’t coming from an adult in the room can sometimes land differently for students, reducing the personal sting while still reinforcing core writing principles.

My Guiding Principle: The Bottom Line

A framework I rely on comes from a former colleague who worked in admissions at Columbia. She called it "the bottom line": a one-sentence summary admissions officers write after reviewing an application. I use it with every student: “After reading this essay, an admissions officer will say ‘[your name] is ___.’ Fill in the blank. What do you want an admissions office to know about you? What do you think they learned after they read this particular essay?” If students have trouble answering those questions, it’s a sign we need to refocus.

This exercise provides clarity. It gives students a North Star for their revision process. When they're drowning in details or unsure which story to tell, the bottom line pulls them back to what matters: Who are you, and what do you want readers to know about you?

A Year-Long Process That Works

The timeline we're navigating is unforgiving. Deadlines start October 15 for many southern schools, then continue every two weeks through early December. Students may spend weeks on an essay, while admissions officers spend 90 seconds to two minutes reading it. That reality makes our mission clear: reduce stress by providing support and clarity throughout the process, so those 90 seconds capture something authentic and meaningful.

Because I start the essay process in May and support students all along the way, when October comes, they are ready to refine the work that they have developed over months. My approach transforms anxiety and uncertainty into thoughtful preparation and the discovery of their authentic voice. In a boarding school where conformity feels safe, the college essay becomes a rare invitation to stand out, and my role is to make that invitation feel exciting rather than risky, so every essay reflects who students really are, not who they think colleges want them to be.

About the author

Shana Russell is the associate director of college counseling at a boarding school in Connecticut. She can be reached via LinkedIn.