Why I Gave My Son Permission to Drop Out of High School

We see a child in a maple tree
We’re watching him climb,
You and I.
You say, “Come down,
You’ll hurt yourself!”
I say, “Go up
You’re touching the sky!”

– “Seeing Things” by John Kander and Fred Ebb

Those who’ve been reading me regularly might remember that my middle child has been begging to drop out of school since he was in third grade. Because my husband and I believed that a nine-year-old wasn’t the best judge of what he did and did not need academically—and because, in all honesty, we thought that learning to do things you didn’t necessarily want to do in the short run so that you might reap benefits in the long run was a critical life skill—we negotiated the following deal: He would stay at his extremely rigorous current school until eighth grade, and then he could skip high school and go straight to college.

Our son kept his part of the bargain. He grudgingly swallowed his displeasure and got grades and test scores high enough that he was able to apply to college at age fourteen. Unfortunately, the institution that accepted him without a high school diploma, wanted more money for tuition than we were paying for his older brother to attend an Ivy League university. Not only was the price tag objectively not worth it, but we couldn’t afford it, anyway. 

So we investigated going the CUNY route. Affordable, close by, the perfect solution for the underage student! Except that, as I wrote in August 2018:

The City University of New York told me they won’t let applicants take its placement test without a high school diploma. But, get this! Over 50 percent of teens who graduate NY high schools with a HS diploma can’t pass the CUNY placement test! However, in a Catch-22 worthy of George Orwell’s doublethink, passing the placement test won’t get you a high school diploma!

Alright, then, we’d sign him up to take the high-school equivalency Test Assessing Secondary Completion (TASC) Exam. Nope! You have to be at least 17 years old. And that doesn’t mean you can take it the day after you turn 17. It means you have to take it at the end of the academic year during which you turned 17 which, for my son, would have meant a few months short of his 18th birthday.

“I am truly sorry,” I told my son, “It looks like you’re going to have to go to high school, after all. Just try it for one year,” I pleaded, “you might like it!”

We chose Stuyvesant High School, supposedly the most academic of the schools he’d gotten into.

We weren’t going in blind. My husband is a Stuy alum, I went to a similar, screened high school in San Francisco (the same one Chancellor Carranza’s daughter attended), and our older son graduated from Stuy in 2017.

We were familiar with teachers like the one who told my oldest, “Don’t think, just tell me what’s in the book.” And the one who claimed she could guess your native food just by looking at you. And the one who heckled kids in the accent that matched their apparent ethnicity. We knew about teachers who took months to grade a single piece of work, and an administration that didn’t care how many Regents you’d passed, if they said you were taking the class again, you were taking the class again—because it made their scheduling easier. 

My older son was worried about how his brother would fare at Stuyvesant. “These teachers don’t know what to do with a kid who asks questions instead of just knowing all the answers.”

I told my middle child, “You won’t like all the classes, you won’t like all the teachers, but, I promise you, you will like some of the other kids.”

And he did. There were also teachers he adored. And subjects he found interesting. There were definitely kids he liked. That wasn’t the problem.