Should I Send My Kid to Boarding School? Questions to Work Through That No One Talks About
Last Tuesday, my 14-year-old Lila slid a crumb-strewn boarding school brochure across our kitchen table, next to her half-eaten peanut butter toast. “Mia from theater goes there,” she said, picking at a loose thread on her cross country hoodie. “They let you do cross country and after-school rehearsals without skipping half of either. I’m tired of feeling like I’m letting everyone down.”
I grew up with boarding school. My mom sent me away at the same age Lila is now, right after my parents split, and I spent most of sophomore year sneaking calls to my best friend, counting down the days until I could come home for good. My older sister also ran away from her boarding school halfway through junior year. So when Lila brought this up, my first instinct was to say no, immediately, before I even looked at the brochure.
But I couldn’t. Lila’s been complaining about the conflict between her two favorite activities for a year now, and we’ve tried everything at our local public high: swapping electives, talking to counselors, even asking the athletic director to adjust practice times. Nothing stuck. This was her idea, not mine, and that’s a big difference from my own experience.
I’ve spent the last six weeks scrolling through generic advice that says “it depends on your kid” which tells me nothing, so I started working through this in small, concrete steps that have helped me sort through the noise. The first thing I did was get a sheet of paper and write down every bad feeling and bias I carried about boarding school, all tied to my own experience: I thought my mom sent me away because she didn’t want me, I hated sharing a bathroom with 12 other girls, I missed our old dog every single day. I folded that sheet up and put it in a junk drawer, then started a new list, this one only for Lila. Separating my baggage from her needs sounds obvious, but I’d never seen anyone suggest writing it down like that, and it made a huge difference. I could see clearly that my fear wasn’t automatically her future.
Next, I had her help me split all her wants and complaints into two columns: things that can only change if we go to boarding, and things that can be fixed where we are. It’s way more useful than a standard pros and cons list. Right now, Lila’s tested a full year ahead in math, but our local high can’t move her up this year because of staffing shortages. That’s a problem that won’t go away between now and graduation unless we switch schools, so it goes in the first column. She’s sick of the drama with her friend group that cycles through the same fights every month, but that’s the kind of thing she’d run into anywhere, so that goes on the “fixed with time” side. When she said she’d miss our golden retriever, Max, I checked the boarding school’s visitor policy: they allow day trips home any weekend that doesn’t have a game or performance, so she can come back once a month to see him if she wants. That’s a con that turns out to be solvable, not a dealbreaker.
A lot of people don’t mention that most boarding schools will let your kid stay an overnight or weekend with a current student, instead of just doing a one-hour campus tour. We did that last month, and it cut through all the polished tour guide talk. Lila came back with a coffee stain on her sweatshirt from the 10th grader she stayed with and a list of very specific small complaints: the showers are too cold, the dorm common room TV only pulls up Netflix, no one keeps good chocolate snacks in their rooms. But she also said she got to stay after rehearsal to work on her monologue without having to rush to catch the last bus, which she can’t do here. That’s the kind of real information you can’t get from a website.
I ran into our neighbor Bill a couple weeks ago, whose son just finished his first year at boarding, and he gave me the best question I’ve heard so far. He said he stopped asking his son “are you sure this is what you want?” and instead asked, every time they talked through the decision, “What’s one thing that sucks about going, and one thing you wouldn’t get if you stayed?” It keeps the conversation from turning into one big emotional yes or no, which is overwhelming for a kid that age. I started asking Lila that, and one week she says the thing that sucks is she’d have to share a room with someone she doesn’t know, and the good thing is she wouldn’t have to miss a single cross country meet for a rehearsal. The next week the bad thing is she’d miss grandma’s 70th birthday, and the good thing is they let you start your own podcast after school if you want. It’s messy, but it’s real.
The other thing no one talks about much is all the hidden costs. I sat down and added up everything, not just tuition: there’s the $500 theater materials fee, travel back and forth for holidays, the dress code that requires new polos and closed-toe sneakers that fit the rules, even the extra spending money for snacks and weekend off-campus trips. We get enough financial aid to make it work, but it means we put the family trip to Japan we’ve been planning for three years on hold indefinitely. That’s a real trade-off, no way around it, it’s not a bad thing, just something we have to accept.
We still have two months before we have to send in the enrollment deposit. We’ve already talked to the counselor at the local high, and she agreed to hold a spot for Lila next fall if she tries boarding and hates it after the first semester. We told Lila that’s the plan: no guilt, no “you made your bed now lie in it” if it doesn’t work out. Right now, we’re leaning towards letting her go, but nothing is final. Last night, we were folding laundry together, and she asked if I thought she was making a bad decision. I told her I don’t know. I can’t know. All we can do is make sure we have a way out if it’s wrong, and take it one semester at a time. That’s enough for now.
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