Going through the boarding school essay process with my daughter taught me a lot about what makes these essays work. I'm not an admissions expert, but the experience of writing essays for eight schools gave me perspective on where things can go wrong—and how to avoid those problems from the start.
These are challenges we navigated carefully, and in one case, a timing issue we dealt with that I'd handle differently if I could do it over. In this article, I share observations about: (1) parental involvement; (ii) how essays should not be used as a proxy for a resume; and (3) how helpful campus tours were in making the student essays far more easier to draft.
The Parent Involvement Line
One of the trickiest aspects of boarding school essays is figuring out where helping ends and over-involvement begins. As a parent, you want your child's essays to be good. When you're a reasonably articulate adult and you can see what your child is trying to say but struggling to express it, the natural temptation is to want to step in to 'fix it.'
The challenge is that essays need to sound like they were written by a 13-year-old. The moment you start imposing your framing, or original ideas, or phrasing over an interpretation of your child's experiences, the essay stops being theirs.
What we did: I focused on asking questions rather than providing answers. When my daughter was working through why she wanted boarding school, she initially struggled to articulate it without making her current school sound inadequate, which wasn't what she meant. Rather than telling her how to reframe it, I asked her what she valued about her current school and what specifically she was looking for that was different. She came to reframing herself, and anchored on the fact that her current school is intimate and rigorous, but boarding school offers a distinctly and uniquely rich learning environment, as well as the independence she wanted to experience. She of course, had substantiating points for why the immersive learning experience, community, and independence appealed to her (which she came to herself, after several series of, "okay, yes, but why / what specifically about it" questions).
My job was to help her access her own thinking through questions. Her job was to be painstakingly deliberate, thoughtful, and introspective, so she could eventually come up with the precise words to describe her feelings and ideas.
How to Navigate This:
- Ask open-ended questions that help your child figure out what they think. Avoid leading questions that embed the answer you want them to give.
- If you catch yourself rewriting sentences to make them "sound better," stop. That's the clearest sign you've crossed from helping to doing.
- Read drafts aloud together. If phrases sound like something your child would never say in conversation, they shouldn't be in the essay.
- Focus your feedback on whether the essay clearly expresses what your child is trying to communicate, not on making it more sophisticated.
- Give time for your child's ideas to kick around and take shape. We often would start / revisit essay prompts, go through 1-2 iterations, and then return back to them in a week or two or more.
For a more in-depth overview of our approach, see: Brainstorming and Feedback Guide.
Essays Are Not Résumés
It's natural to think of essays as an opportunity to make sure Admissions Officers know about your child's activities and achievements. But that information already exists in other parts of the application. Essays serve a different purpose—they're supposed to reveal something about how your child thinks, what matters to them, and who they are beyond their credentials.
I made sure my daughter understood this distinction early on. The question her essays should answer wasn't 'what have I done?'; rather, it was 'what does this mean to me / what is the journey I took to do this thing I've done?' When she wrote about her interests—digital art, ceramics, physics, theater, we did not try to create a cohesive narrative or strategic 'brand.' She simply wrote about why she's drawn to different things, how it became that she is drawn to a variety of things, and how she thinks about each of the things, even though they might seem scattered to someone else.
This approach felt risky because it meant leaning into her eclecticism rather than packaging her more neatly. But the essays felt authentic because they were about who she actually is, not just what she's accomplished.
How to Approach This:
- Remember that Admissions Officers already have the activity list and transcript. Essays exist to show something different.
- Look at the balance in early drafts between 'what I did' and 'what it meant to me.' If it's heavily weighted toward accomplishments with minimal reflection, keep working.
- Small, specific moments often reveal more about a person than summaries of impressive achievements.
- Encourage your child to write about what genuinely matters to them (even if it might seem mundane or basic).
The Campus Tour Timing Challenge
This is the one issue we dealt with directly. We started working on some essays before my daughter had visited all the schools she was applying to, and it created a real challenge. Writing authentically about a place you've only seen on a website is difficult—the essays end up vague and generic because there's nothing concrete to anchor them (for transparency, we started working on essays before the interviews as a forcing mechanism to prepare for interviews).
Once my daughter had actually visited schools, the writing became significantly easier. She had specific details and opinions to inform her feelings. More importantly, she had genuine feelings about the schools based on real experience, as opposed to abstract impressions from promotional materials.
Why this matters: The 'why this school' prompts went from feeling like an obligation to being relatively straightforward because my daughter could write about actual experiences. She could explain why Groton's smaller community appealed to her differently than Exeter's size because she'd spent time in both environments. Without those visits first, the essays would have been more generic.
If I could do it over, I'd make sure every campus tour was completed earlier, so my daughter could have real fodder for drafting school-specific essays.
How to Handle This:
- Schedule campus tours before starting school-specific essays if at all possible. The writing will be substantially easier and more authentic.
- If timing constraints make this impossible, focus first on general personal statements and save school-specific prompts until after visits.
- During tours, take notes—both you and your child. Small details that seem obvious at the moment are hard to remember weeks later when drafting essays.
- The difference between writing about something you've researched versus something you've experienced is significant and noticeable.
What Ties These Together
All three of these challenges stem from the same thing: understanding what boarding school essays are actually supposed to do. They're not polished writing samples where correctness matters most. They're not marketing documents designed to showcase credentials. They're a way for a 13- or 14-year-old to help Admissions Officers understand who they are, how they think, and why they're interested in this particular experience.
My advice: Help your child think through their ideas without imposing your words. Make sure essays focus on reflection and genuine interest rather than accomplishment summaries. Visit schools before writing about them whenever possible. These approaches made our essay process work, and they can help you avoid the pitfalls that would make it harder than it needs to be.