Diary of a Soon-to-be Middle Schooler’s Mom

Tomorrow is Grady’s last day of elementary school. After 10 years of class-momming the heck out of this kid, it’s time to take the next step.

I must bravely go where no mom has gone before—in my shoes, at least. It will be my first-last time sending Grady to elementary school.

Looking back over the years, I have a few favorite memories.

Preschool 1 (Boulder): When we sent 18-month-old Grady to a Montessori school and they politely asked us if we were “sure this was for him” after the first day when he spent 4 straight hours banging on the same drum.

Preschool 2 (Boulder): After that one day of Montessori school when we found Grady’s comfort zone—a disorganized, play-based, crazy-town preschool.

Preschool 3 (Boston): Where Grady dressed like a pirate 5/5 days a week.

Preschool 4 (Miami): Where Mrs. Howell gave Grady his favorite nickname, Captain Pickles.

Preschool 5 (Miami): When Grady spent the majority of the academic year hopping like a frog. His quads were to die for.

Kindergarten (Miami): When Grady learned to sing “Proud to Be an American”—and never stopped.

First Grade: (Miami) When Grady declared he was allergic to baseball practice. And tennis. And sports.

Second Grade (Miami): When a fellow student was crying in the corner of the Frost Science Museum on a class field trip because he was being left out. I witnessed Grady sit down next to him, rub his back and tell him, “Come with me. I’ll get you in the game.” And he did.

Third Grade (Miami): When Grady dressed as Super Mario and asked his father to be Luigi and walk with him in the school Halloween parade—which, of course, Jason did not question.

Fourth Grade Part 1 (Miami): When COVID was hot and heavy and Grady obliged his mother by reciting the Pledge of Allegiance each morning before Zoom school.

Fourth Grade Part 2 (Albany): When Grady wore his first Catholic school uniform and learned the Our Father.

Fifth Grade (Mahwah): When Grady bravely marched into a new school in New Jersey with a smile and a giant heart ready to make new friends—but first ran back to the car to tell me, “Don’t worry. Ok, Mom?”

Middle school wasn’t a walk in the park for most of us. We often look back and thank God we don’t have to do THAT again. But something tells me Grady will be just fine. I will be a total wimp and worry each and every day. But Grady will find a way to get through it and come out sweeter and stronger than ever. He always does.

Bravo, Grady. You’re simply my favorite boy in the world.

Boston 2013 / Preschool 3
Mahwah 2021 / 5th Grade