School isn’t supposed to be fun

The case against constant educational optimization

This week, I spoke alongside Sophie Brickman (buy her book!) at an event hosted by the Tutoring League of NYC (join their group!), addressing an audience of parents, teachers, and education consultants about (mostly private) school choice in New York City. The conversation centered around the abundance of options available to well-resourced parents and whether this wealth of choice is a blessing or a curse.

A recurring theme emerged: the idea that children may not “thrive” in the same environment the whole time. That a school that’s a good fit for kindergarten might not be the right fit for middle and high school. 

Here's my concern: this notion that our kids should be "thriving" can be misleading. When we talk about thriving, we conjure images of happiness, comfort, and engagement. But here's the truth: school generally looks nothing like that. So when schools advertise those sorts of images, they create unrealistic expectations for parents and kids, which often leads to self doubt and disappointment, and families find themselves on a perpetual yet misguided hunt for something better.

School is frequently boring. It's tedious. It's frustrating. It's hard. It's uncomfortable. When children are growing and expanding their abilities, it usually looks messy and feels unpleasant.

At the Tutoring League talk, I tried to explain the approach I’m taking to educating my daughter. Barring serious issues—say, systematic, intractable bullying or the discovery of learning needs that necessitate a more restrictive environment—I’m viewing her school placement as more or less permanent. My line of work means that I'm pretty well-versed in education research, so I know that most of the variables parents obsess over (even seemingly important ones like class size) will have surprisingly little impact on her educational outcomes. So instead, I want to make sure my daughter learns something I think is more valuable: how to navigate imperfect situations. How to learn even when she doesn't particularly like her teacher. How to push through when the material is boring or confusing. School, like the world in general, won't always cater to her preferences, but she needs to make it work nonetheless.

Also, perhaps even more importantly, I want her to work really hard and to wear her effort like a badge of honor. In an era where it's fashionable to put on an air of effortless achievement—to be the straight-A student who "never studies"—I want my daughter to take pride in sweat and elbow grease. To understand that struggle isn't a sign of weakness, but a requirement of growth. And to feel the genuine satisfaction of mastering a concept after weeks of wrestling with it. There's a particular sweetness to victory when it follows genuine struggle: a feeling that can't be replicated by breezing through material. I want her to know that feeling intimately, to recognize it as the reward for persistence rather than talent, and to understand that this is what learning is supposed to feel like.​​​​​​​​​​​​​​​​

So I told the group that, by constantly seeking the perfect environment where our children can "thrive," we might actually be depriving them of the chance to develop grit and resourcefulness. Sometimes, the most important growth happens precisely when we don’t feel like we’re thriving—when we're struggling, adapting, and pushing through. That's not just education; that's life.

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I have never been so excited to see a movie in my whole life, but what is Wicked without Norbert Leo Butz??