What Former Private School Students Hate Most About Their Education: What Parents Need to Know
Last month, my college roommate Lila sat across my coffee table, crumbs of oatmeal raisin cookie sticking to the sleeve of her sweater, while my 11-year-old son flipped through a glossy open house flyer for the private middle school down the road. He’d heard me and my husband talk about whether it’d be a good fit for his robotics obsession, and halfway through our catch-up, he looked up and asked, “You both went to private school, right? What did you hate most about it?”
We both laughed first, because the easy answer is sky-high tuition or too much homework, but that wasn’t the real thing that stuck with us after all these years. Lila went to an all-girls day prep outside Boston, paid for by her grandparents, and she answered first. She said the thing she still hates thinking about is how there was no room for small, normal mistakes. Sophomore year, she got a B+ on her chemistry midterm. She’d never gotten lower than an A before, and she’d just had a brutal cold the week she studied. Her teacher pulled her out of study hall anyway, and asked if something was wrong at home, if she was struggling with depression, because a B+ “wasn’t like her.” By the end of the conversation, Lila said she left convinced something was actually broken in her. Twenty years later, she still panics if a work project gets less than glowing feedback, even for tiny, low-stakes tasks.
I went next. My parents worked extra side jobs to pay tuition at my coed day private school in Portland, because they were convinced it’d get me into a better college than public school could. The thing I hated most was the quiet, unspoken shame around money. Everyone wore the same uniform, but new polo shirts from the school store were $50, and if you bought yours from the secondhand swap everyone could tell by the faded logo. We had a mandatory three-day ski trip for PE every winter that cost $350, not including equipment rental. My sophomore year my mom got laid off, so I couldn’t go. I had to sit in the school library for three days while everyone else posted photos from the mountain to their new Facebook accounts. No one asked why I wasn’t going, no one offered to help. I just told people I didn’t like skiing, and I still avoid group trips where I have to pay extra to participate to this day.
After Lila left, I sat with that question for a while. We’re both parents now, Lila has a 13-year-old in public middle school, and I’m right in the thick of deciding where my son will go next year. The thing no one mentions in private school brochures or admission tours is that most of these schools are built around a culture of perfection. They sell you small class sizes and high Ivy League acceptance rates, but that comes with the expectation that every kid will fit the mold of the high-achieving, well-off student that builds the school’s reputation. Small dips in grades, not having extra money for activities, even just wanting to slack off one weekend are seen as problems to fix, not normal parts of growing up.
That’s not to say private school is inherently bad, or that every school has this problem. But after our conversation, I started asking specific questions on tours that I never would have thought to ask before, and I’ve started building small routines at home to counteract these issues if we do end up enrolling my son.
The first question I ask every admission counselor is, “If a student who usually gets A’s gets a B on a major test, what does the school do first?” If the answer starts with “we reach out to the family to create an improvement plan,” that’s a red flag for me. A kid can just have a bad week. They don’t need a formal intervention for one bad grade. If the answer is “we expect grades to fluctuate, and we encourage the kid to talk to the teacher if they need extra help,” that’s the answer I’m looking for.
The second question I ask is about optional trips and extracurriculars that cost extra. I ask what the school does to support kids who can’t afford the fees, and how they make sure those kids don’t feel left out. If the school says they have 100% confidential need-based grants that cover full cost for any kid who needs it, that’s great. If they shrug and say “most families can afford it,” that’s an immediate no for me.
If your kid is already in private school, there’s a low-effort routine you can add at home to push back against the perfection culture. We started a thing at our house where every Sunday dinner, everyone has to share one small mistake they made that week that didn’t really matter. My son usually talks about tripping in the hallway or forgetting his math homework. I talk about burning the toast or missing a work deadline by an hour. We laugh about it, no one gives advice or tries to fix it. It just normalizes that messing up isn’t a big deal, and it doesn’t change how anyone sees you. It takes 10 minutes a week, no extra money or planning, and it’s already made a difference in how my son talks about bad grades he gets at school. I also talk openly about money with him— I tell him when we can’t afford something, and when we can, and that it’s not shameful to need help.
We’re still deciding about the private school for my son. Their robotics team is one of the best in the state, and that’s something he cares about deeply. We can afford tuition, and we’ve already talked through what boundaries we’ll set if he goes: he can skip any expensive trip he wants, no shame attached, and bad grades don’t automatically mean extra tutoring or consequences at home. I didn’t love my time at private school, but it wasn’t all bad— I had great math teachers, and I made lifelong friends. But I wish someone had told my parents what the real, unspoken downsides were back when they were signing the first tuition check. We’re taking it one open house at a time, and right now, that’s enough.
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