Choice #3: Should I Send My Daughter to Private School?

Unlike many private schools around the world, the one I attended from kindergarten through 12th grade was small, well-regarded, and—most importantly to my family—financially conscious. Living on Maui, schooling options are limited, and the private schools that do exist are scattered across the island. Commutes can range anywhere from 10 minutes to over an hour. So when my parents learned that I’d been accepted into a private school located right in our hometown, they were ecstatic.

Both of my parents were teachers. Education was deeply important to them, and they wanted to make sure my sister and I understood its value. But as teachers, their income wasn’t extravagant. Fortunately, through financial aid and scholarships, they made it work.

Now, 20 years later, I’m facing the same decision—but this time, as a parent. The difference? Tuition has tripled, and we’ve just been informed we won’t be receiving any financial assistance. Not a dime. Despite being a dual-income household with stable jobs, a mortgage, and the usual financial obligations, we don’t qualify for aid. I know we’re fortunate in many ways, but when you add a massive monthly tuition to the mix, it becomes a serious financial stretch.

So here I am, asking myself:

Should I send my daughter to private school?

If you’d asked me ten years ago, I would’ve said yes—without hesitation. Of course I’d want her in a school with great resources and opportunities. She’s my kid! I want her set up for success. But I wasn’t prepared for what that cost actually means. It’s not just fewer vacations—it’s fewer grocery trips, smaller holidays, and more of those classic mom lines like, “No, we’re not eating out. We have food at home.”

Honestly, I was angry at first. Angry at the system. I caught myself asking questions like, “How did I do everything right and still end up barely getting by?” and “Why does the middle class always seem to get the short end of the stick?”

Those weren’t my proudest moments, but they were real.

And yet, the question remains. Is it worth it?

My boyfriend and I love the school. We think it would be great for our daughter’s development. But…it’s preschool. It’s not like she’s taking calculus. She can learn her ABCs at a public school, too. And maybe I don’t want her in a hyper-curated environment anyway. Kids in the ‘90s, like us, grew up in public schools just fine. They got scrappy, built resilience. She’s already smart—she doesn’t need to know the alphabet in three languages just yet.

As I write this, I find myself rattling off a list of cons about private school—and typing with enough force that I’m sure my neighbors can hear. But why do I feel so strongly now that it’s a financial burden? To gain perspective, I called my mom. I figured, She had it easier. They got aid. It was a no-brainer for them.

Turns out, it wasn’t.

She told me, “No—it was not an easy decision. We didn’t even want to send you to that school at first. We wanted another private school that cost way more. But we were willing to make it work.”

Wait…what?

All this time, I thought they had it easy. That the choice was obvious because of the cost. But it wasn’t about money at all.

She continued: “We just wanted you to be somewhere you’d feel comfortable. You were so shy. At your school’s admissions play session, you just sat alone while the other kids played. We were watching from inside the classroom window—parents couldn’t interact. But then, one little girl came over and sat next to you. She didn’t say much, but you perked up, grabbed her hand, and started playing. You’d never done that before. When we saw that, we knew it was the right place for you. And we were right—you’re still friends with her to this day.”

That story hit me hard.

School isn’t just about academics. It’s where kids learn to be kids. It’s where they scrape their knees playing two-square, discover they love dinosaurs, butterflies, or the color blue. It’s where they start to find their people.

So…should I send my daughter to private school?

Answer: It’s not about whether it’s private. It’s about whether it’s her school—a place where she feels safe, happy, and ready to grow. So yes, we’re going to send her. Not because it’s private, but because it feels like the right fit.