Should My Child Go to Boarding School? What I Learned Helping My Teen Decide
The crumpled boarding school brochure slid across our kitchen table Tuesday night, landing in a puddle of leftover pizza grease next to my 14-year-old Lila’s half-empty cherry soda. I was folding her swim practice laundry when she pushed it toward me, picking at a loose thread on her hoodie. “I want to look at this,” she said. I’d known this moment was coming for months, but it still caught me off guard. Lila’s a competitive distance swimmer, and for a year she’d been juggling 5:30 a.m. practices, after-school training, and a full load of classes at our local public high. Some nights she’d fall asleep at the kitchen table before finishing her math homework, too tired to even drag herself to bed. She’d complained for months that she couldn’t keep skipping meets for midterms, or skipping study halls for practice.
I’d always thought of boarding school as something for kids whose parents couldn’t handle them, or for wealthy families who wanted a fancy college resume. I never thought it would be an option we’d actually consider. But over the next two months, we worked through the decision step by step, and I learned a lot of what I thought I knew was wrong.
First, we did tours over spring break. The first one was an hour away, all red brick and mandatory uniform polo shirts, the admissions rep talked nonstop about college acceptance rates the whole time. After we left, Lila got in the car and said “I felt like I was visiting a fancy prison. No one even smiled.” The second was smaller, right outside of Portland, with a swim program that sent three kids to Olympic trials the year before. After the tour, the coach let Lila jump in the pool for a 20-minute easy swim, and introduced her to two other 14-year-old swimmers who attended the school. She talked to them for 45 minutes after her swim, standing by the locker room, asking about homework loads and how often they got to go home. That night, she didn’t complain about the drive home, just scrolled through the school’s swim team Instagram over and over.
I knew a 2-hour walking tour with an admissions rep wasn’t enough to get a real feel for the place, so I called the office and asked if Lila could stay a full weekend with a host student. Most boarding schools offer this for free to prospective students, something I didn’t know before I started looking into options. She went that April, came home with chipped pool nail polish and a crumpled drawing the host student’s little sister had given her, and only cried for 10 minutes in the car about how much she missed our old beagle. That’s when I knew she was actually serious, not just caught up in a new idea to escape the daily grind.
We did a few other small, concrete things that made the decision clearer, instead of just guessing and worrying. First, we each wrote our own pros and cons on separate index cards, then taped them to the fridge. No combining lists first, no telling each other what to include or leave out. Lila’s top pros were “no more skipping practice for tests” and “everyone here swims, so no one calls you obsessed for leaving parties early.” Her top cons were “I’ll miss Tuesday taco nights” and “I won’t be here for my little brother Jax’s first middle school soccer game.” My top pros were “she’ll get 2 more hours of sleep a night” and “she won’t have to choose between the thing she cares about and her grades.” My top cons were “we can’t afford this without dipping into retirement savings” and “if she has a bad day, I can’t be there in 10 minutes with hot cocoa.” Putting it all out like that made it easier to see what actually mattered, instead of just panicking about what other people would think. My sister commented at a family dinner that I must be glad to get Lila off my hands, and that stung, but when I looked at our fridge full of pros and cons, I knew we weren’t doing this for us. We were doing it for her.
I also reached out to two local parents I knew through the swim club who had sent kids to boarding school, instead of only listening to what admissions teams told me. One told me her kid, a cross-country runner, struggled the first six weeks with homesickness, but by second semester he was calling less and was way more relaxed when he came home for breaks. The other told me her daughter hated it, came home after a year, and that was okay—they just re-enrolled her in the local high, and it all worked out. That took a lot of the pressure off, because I realized even if we made the “wrong” choice, it wasn’t permanent.
Right now, we’re two weeks out from the enrollment deadline. We put down a deposit to hold Lila’s spot, so we have time to decide, and she can still back out and stay at the local school if she changes her mind. If she goes, we already worked out a check-in schedule she’s comfortable with: no mandatory nightly calls, which she says make homesickness worse. Just a quick text every day to check in, a longer call every Sunday night, and we’ll drive up to watch every home meet, bring her favorite chocolate chip cookies that the dining hall doesn’t make. If she stays, we already set up a meeting with her high school principal to ask for flexible test scheduling for when she has to leave for meets.
I still don’t know what she’ll decide, and I still don’t know if it’ll be the right call if she goes. I’ll miss her leaving wet towels on the bathroom floor, and late night talks on the couch after bad meets, and our stupid Tuesday taco nights. But I also know she’s tired right now, and she’s constantly splitting herself in two to keep everyone happy. Whatever she chooses, we’ll make it work. There’s no perfect answer here, just the right answer for our kid right now.
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