How to Decide If Your Teen Should Go to Boarding School: A Parent’s Real Experience
It’s 9:45 on a Tuesday night, the dishes are still in the sink, and my 15-year-old Lila is leaning against our fridge twisting an acceptance letter between her fingers. Half a peanut butter cracker is melting into the granite counter, the dog is chewing on the toe of her sneaker, and she hasn’t said anything for five minutes. I set down the laundry I was folding and wait. “I don’t know if I want to go,” she finally says. “I just know everyone keeps asking me, and I still don’t know.”
She applied back in October, after a field trip to the arts boarding school an hour and a half from our house. The local high school only offers one 45-minute art class a day, and Lila has been painting on every available surface since she was 8—old canvases propped on her desk, half-finished murals on the back of her closet door. She applied on a dare from her middle school art teacher, we didn’t think she’d get the partial scholarship we needed to afford it, and here we are, two weeks out from the deposit deadline, stuck.
My first reaction when the acceptance came was equal parts excitement and cold panic. I’d always pictured her walking to the bus stop with her best friend, going to our town’s annual homecoming parade, sleeping in her messy room down the hall every night. Everyone I tell has an opinion: my sister says she’ll grow so much from being independent, my neighbor says I’m crazy to send her away when she’s still young. None of it helps. All the generic advice just floats around us, no closer to an answer.
I started with the classic pro-con list. We sat at the kitchen table, wrote Pros on one side of the notebook page, Cons on the other. After 10 minutes, Lila had “more art time” under pros and “no Sunday cereal” under cons, and that was it. She said it felt stupid, because none of the lines felt big or small enough to capture how she actually felt. So I scrapped that, and tried something another parent had mentioned to me months earlier: instead of listing pros and cons, we wrote out a typical Monday for each option.
For boarding: Wake up at 7, breakfast in the dining hall with other kids, three straight hours of open studio before lunch, two academic classes after, open studio again until 6, dinner, study hall, hang out in the dorm common room until lights out. For our local high school: Wake up at 6:15 to catch the bus, one 45-minute art third period, cross country practice after school (she only joined because her best friend did, she hates running), get home at 4:30, homework until 7, 45 minutes to paint before bed, shower, sleep. When we finished writing, Lila stared at the page for a minute and said, “The boarding Monday sounds like what I want my life to be. But I don’t know if I can actually not come home every night.”
Next we did the overnight stay the school offers for prospective students. She packed her bag, forgot her childhood stuffed fox that she still sleeps with, called me at 9pm panicking from the dorm lobby phone. I drove up, brought it, sat in the parking lot for 10 minutes while she hugged me and said she already missed the dog. I didn’t tell her to suck it up or push her to stay and give it a chance. I just gave her the fox and said I’d be back at 9 the next morning, no pressure either way. When I picked her up, she talked the whole way home about the girl in the next dorm who paints large-scale murals of abandoned barns, and how they stayed up until 11 talking about applying to art college. But she also stopped mid-story halfway home and said she still missed our usual Sunday morning routine of cereal and terrible British baking show reruns.
Over the past few weeks of working through this, I’ve picked up a few small, concrete things that help way more than all the opinions from other people. First, stop asking open-ended questions like “what do you want to do?” Teenagers that age can’t wrap their head around a big, life-changing question like that. I started asking three specific questions that got her talking: What’s one thing you’d get at boarding that you can’t get here? What’s one thing you’d miss so much it would make you sad most weeks? If you try it for a semester and hate every minute, what’s our backup plan?
That third question is the one that made the biggest difference. A lot of people frame boarding as a forever choice, but it doesn’t have to be. I called our local high school principal, explained the situation, and she said Lila could always come back mid-year, no extra hoops, no problem getting slotted back into her original classes. We told Lila straight out: it’s not failure to come back. It’s just trying something that didn’t fit. That took a huge weight off both of us. We also planned for small, regular touch points: she can come home every other weekend, I can drive up for lunch on Wednesdays if she’s having a bad week, no questions asked.
The deposit deadline is this Friday. We still haven’t hit send on the payment. Lila said last night over pizza that she thinks she wants to go, but she still worries her best friend will make new friends and stop texting her. I don’t have an answer for that, because that could happen either way. What I do know is that we didn’t rush it, we didn’t force her to pick a side just to make us feel better, and whatever she picks, we have a plan if it doesn’t work. That’s more than I had when we started, and that’s enough for right now.
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