I wrote a post a very long time ago about how you can still be sad about your kids growing up even when they’re not your last child. I was pregnant with my fourth child then; she’s now 7 1/2 and on her way to second grade soon!
But I’ll have to admit the transition that is hurting my heart this year is that my third child, Joshua, is “graduating” fifth grade and heading to middle school. 
Yes, I’ve done this twice before. And honestly, they were harder transitions for my two older kids! My oldest didn’t even get to finish her fifth-grade year because it was 2020; both she and her next younger brother changed schools after fifth grade as well.
But for some reason I’ve always had the hardest time with the fact that my third baby is growing up.
Maybe it’s that he is tiny, still speaks with a little bit of a lisp, and with his wild imagination seems very much like a little kid.
Maybe it’s that he was the baby for 3 1/2 years and I never stopped babying him.
Maybe it’s that he’s still cuddly and sweet and loves his mommy.
When I dropped my older two kids and even the youngest at kindergarten, I was really okay. It was difficult because it was a transition, but they were more than ready.
When I left Joshua in kindergarten, I cried for three days.
I wasn’t quite sure he was ready for kindergarten and that I had made the right choice. And now, facing middle school, I wonder again if we should have held him back and let him be little for another year.
And when he’s feeling the same way, it’s even harder for me not to grieve more. Just this morning, he told me he wasn’t ready to leave fifth grade…couldn’t they just have another week? Couldn’t his teachers move up to sixth grade with him?
Because he goes to a magnet school, he doesn’t even have to switch schools for next year; he’ll be just down the hallway from his current classroom, with his same friends. But it still feels like a leap. I’ve seen how kids change as puberty hits. I remember how incredibly terrible my middle-school experience was and how hard it’s been for my older daughter and son.
