The Reading Start Perspective

The First Goodbye: What I Learned Watching Hundreds of Children Start School

Last September changed the way I think about school transitions. More accurately, it cemented something I had first discovered as a parent.

I was a teacher for six years before I became a parent. I had seen plenty of children cry on the first day of school, and I thought I understood it. It wasn't until I had to drop off my own children that I realized just how hard saying goodbye can be from the other side of the classroom door. Like many parents, I thought that staying a little longer was helping.

Over time, I learned that the quickest goodbye is often the gentler goodbye.

As parents, our instinct is to comfort our children when they are upset. We hug them a little longer, reassure them one more time, and sometimes linger because leaving while they are crying feels impossible.

But when children know what to expect, they begin building trust. A calm hug, a confident "I love you. I'll see you after school," and a consistent routine can communicate safety far more effectively than a long goodbye filled with uncertainty. Lingering, although well intentioned, can unintentionally signal that there is something to worry about.

That doesn't mean children won't cry. Tears are a normal response to a new experience. Our goal isn't to eliminate those emotions. Our goal is to help children learn that they can feel nervous, move through those feelings, and discover that school is a safe place where caring adults will support them.

One of the things I observed most often was that children usually settled within minutes after their caregiver left. They joined their classmates, began playing, listened to a story, or became engaged in classroom routines. Meanwhile, many parents drove away wondering if their child had cried all morning. More often than not, they hadn't. If you're lucky enough to get a quick update from your child's teacher or school, that little glimpse of a happily playing child can be incredibly reassuring.

As both an educator and a parent, this experience reminded me that one of the greatest gifts we can give our children is confidence in their ability to do hard things. A confident goodbye isn't about rushing children through their emotions. It's about showing them that we believe they are capable and that we trust the adults we are leaving them with.

Here in New York City, we are on the precipice of a new school year. If your child is preparing for a first day, you don't have to wait until that morning to begin preparing for the goodbye.

Take a drive past the school. Talk about what the morning might look like. Tell your child who will bring them to school, what will happen when you arrive, and when they can expect to see you again. Decide what your goodbye routine will be and talk about it beforehand. Predictability can make something unfamiliar begin to feel familiar.

Books can help with that preparation, too, but I'm always hesitant to hand parents a definitive list for something as personal as separation. Books are not one-size-fits-all, and different stories resonate with different children and families. In my own house, All Day Long and Llama Llama Misses Mama were winners with both of my children. As a teacher, I relied on The Kissing Hand for years, although, ironically, I lent my copy out before I ever got the chance to read it to my children.

And sometimes a difficult transition requires more than a book or a goodbye routine. When I'm looking for guidance specifically around children's emotions, separation, and behavior, I turn to experts in those areas.

Resources I Trust

Dr. Becky Kennedy, Good Inside
For guidance around separation anxiety, children's emotions, and navigating difficult parenting moments.

Jess VanderWier, Nurtured First
For guidance around separation, goodbyes, emotional development, and children's behavior.

Most importantly, remember that a tearful goodbye does not necessarily mean a bad day is ahead. Your child can miss you and enjoy school. They can feel nervous and still walk through the door.

Sometimes our job as parents is simply to give them a hug, tell them we love them, and show them through our own confidence that we believe they can do the next hard thing.

About The Reading Start Perspective

The Reading Start Perspective shares lessons I've learned through my experiences as a classroom teacher, parent, literacy researcher, and elementary school dean. These reflections aren't meant to replace individualized guidance for every child or family. Instead, they bring together research, professional experience, and the everyday moments I've witnessed while supporting children and families through the early years.