My son Smoke starts kindergarten in less than a week. I should be ready for this. Because he has an October birthday, he’s had to wait until he’s nearly six to start. His friends with March birthdays and August birthdays have, in his eyes, beat him to it and ever since he turned five, I’ve been answering the question “When does kindergarten start?”

Smoke was still in diapers when I learned about the official cutoff dates, and at the time I thought it was a shame that he would have to start so late. I knew that many parents these days were holding off on kindergarten, intentionally waiting until their kids were older, or as they called it “ready.” At the time, I saw this practice as overprotective. For some reason, I was eager to begin my son’s formal education, to watch him learn to read and write, to forge his own way in the world. Also, I’ll just say it: I was looking forward to free childcare.

But over the past year, the year that would have been my son’s first year of kindergarten if I had petitioned for early entrance, I’ve come to question all of my assumptions about his readiness. Now that he’s nearly six, and should be more than ready, I wonder if he’s ready at all.

I wonder if he’s ready for a class of twenty-two students.

My son has gone to preschool since he was two and for a long time I assumed that this meant he’d be amply prepared for kindergarten. Then one day it hit me—his preschool had pretty much the same cast of eight kids for three years. In kindergarten, he’ll share a room with twenty-two kids. For six hours every day. That sounds emotionally exhausting to me, and I guess I should know. I teach groups of 28 college students for two hours at a time, and when I come home my brain is fried. I can barely form a coherent sentence. Sharing one space with that many personalities is work.

I wonder if he’s ready to follow instructions.

I know I’m biased, but I find my son brilliant. He uses big words, tells elaborate stories, and spends hours focused on building tiny sculptures out of Legos. For a while I took for granted that my son’s intelligence guaranteed that his school experience would go smoothly, but I’m no longer sure. Smoke likes to do what he likes to do. His brilliance lies in his ability to concentrate. But this ability, paired with his constant insistence on following his own agenda, will likely be at odds with his ability to learn at school. He’s not so interested in pleasing adults.

I wonder if he’s strong enough and kind enough.

I worry about the pecking order in kindergarten, about the small groups that form, the dynamics of inclusion and exclusion that shift and evolved. I wonder how my son will fare. I worry of course that someone might be cruel to my son, but I worry more that my son might participate in cruelty. I picture those smaller kids, those genuine five-year-olds, the ones with snot bubbles in their noses, or the one who pees his pants on the first day. I sure hope he’s kind to them.

*This post kicks off a new series on Goodnight Already that tracks my son’s transition into kindergarten. I’d love to hear from other parents who are entering the same era. Please consider sharing and commenting if you are so inspired.