Should You Send Your Child to Boarding School? Practical Questions to Help You Decide
Last month, I leaned against our kitchen counter half-loading the dishwasher, staring at the thick cream acceptance envelope that came for my 14-year-old, Lila. She’d applied to the boarding school on a whim, after her best friend’s mom brought it up at a birthday party, and none of us expected she’d actually get in. The sticky Cheerios bowls from her after-school snack were still on the table, and she was curled up on the couch scrolling TikTok, glancing up every few minutes to say, “I still don’t know. What do you think?”
I went to boarding school for high school, and I hated every minute of it. I spent most weekends hiding in the library calling my mom crying, and I left feeling disconnected from our family in a way that took years to fix. So this decision already had my own bias tangled up in it before we even started talking seriously. We visited the campus two weekends ago, walked the tree-lined quads, saw the huge art studio Lila had been obsessing over, the stables for after-school riding. She ran her hand along the pottery wheels and grinned, but when we sat in on an evening study hall, she whispered to me that none of the kids had their phones out, and the Wi-Fi didn’t reach the far dorms anyway. On the drive home, we stopped for gas, and she said, “It’s pretty, but it feels like another world.”
I talked to my sister a week later; she sent her son to boarding school when he was 13, because he was getting bullied at our local public school and couldn’t focus with our chaotic house full of three younger kids. She said it was the best choice they ever made, but she still misses the random 10-minute rants he used to have about bad math teachers over dinner. She told me the thing no one tells you is that boarding school isn’t a fix for anything, it’s just a different place to grow up. That line stuck with me.
Instead of just arguing back and forth about pros and cons on a messy whiteboard (we tried that first, it just gave us both a headache), we started doing small, concrete tests to figure out what fit. First, we did a two-week trial of full independence at home: Lila got herself up every morning, packed her own bag, did all her own laundry, scheduled her own orthodontist appointment, and managed her homework without me reminding her. She forgot her soccer cleats twice, missed one reading assignment, but she figured it out both times—borrowed cleats from her teammate, stayed after class to make up the work. It didn’t go perfectly, but that was the point; we wanted to see if she could problem-solve when things went wrong, not if she’d never mess up.
Next, we did a five-day stay with my cousin who lives two hours away, with the same phone rules most boarding schools have: only a 10-minute call once a day, no constant texting. Lila had a great time hiking and baking with my cousin’s kids, but on the fourth night, she cried a little during our call, said she missed our old dog who sleeps at the foot of her bed. That wasn’t a red flag for me; it just meant she’s normal. Homesickness isn’t a sign you made the wrong choice, it’s just part of leaving home.
I’ve talked to a few other parents who’ve been through this decision, and we came up with three specific questions to ask your kid that get past the generic “I want to go/I don’t want to go” answers. First, ask: Who do you go to when you’re really upset about something? Can you imagine asking an adult at school for that help if we weren’t nearby? Second, ask: What’s the first thing you’d want to do when you come home for break, if you went? If they can’t name anything small and specific—like get your favorite tacos from the food truck down the street, or sleep in your own bed—they probably haven’t really wrapped their head around what being gone most of the year actually means. Third, ask: What do you think would be the hardest part of going, that no one has asked you about yet? Lila said it would be missing the annual family camping trip every August, and that’s something we hadn’t even talked about before.
We also didn’t hide the practical, unglamorous stuff from her. We sat down and showed her what the tuition would mean for our family: it would mean putting off the trip to Japan we’ve been planning for three years, and it would mean she’d have to apply for more scholarships for college than we originally planned. She thought about it for a full day, then said she still thought the art program there was worth it, because our local high school only has one art teacher and no pottery program at all.
We still have two weeks until we have to put down the deposit. Some days Lila comes home from school and talks about how excited she is to have her own dorm room to decorate with tapestries and fairy lights. Other days she says she doesn’t want to miss her best friend’s quinceañera next fall, and maybe she’d rather just stay. I still haven’t pulled my old boarding school yearbook down from the attic; I don’t know if my bad experience is making me too cautious, or if it’s helping me see the hard parts no one posts about on boarding school Instagram pages.
Right now, what’s working is we have pizza every Friday night, and we talk through one small thing about the decision each week, no pressure to have the answer right now. There’s no perfect choice here, one way or the other. We just have to pick the one that fits our kid, right now, today.
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