My Son’s First Day of Preschool: Big Milestone, Small Moments

Stepping confidently into a new beginning, my eldest embarks on his first day of school, backpack in tow and ready for the adventure ahead.

Last week, my son started preschool. 🥹 It’s a funny feeling to say that out loud because he’s been in daycare since he was 14 months old — so in many ways, school isn’t a new thing for him. But somehow, this feels different. Maybe it’s the word preschool, maybe it’s the milestone of it all… or maybe it’s just the reality of watching your little one grow up.

I’ve been fortunate enough to be home with him since December, which gave me a chance to really see him in a different light before this big transition. Over the summer, he went to camp at his new school, which I think was a huge gift. He’s not a kid who loves transitions, so the chance to get used to the environment, the teachers, and even the playground ahead of time helped us both feel more at ease when the “real thing” started.

A Gentle Start: Fiesta + Welcome Day

His school did such a thoughtful job preparing families for this big leap. First, they hosted a back-to-school fiesta — a fun evening where parents could meet each other, teachers could connect, and kids could play together. After that came Welcome Day, where children got to explore their classrooms with parents still present.

By the time Wednesday rolled around, it didn’t feel like we were being tossed into the deep end. Sure, my son was nervous. I was a little nervous too. But it felt manageable, and I think that gentle, step-by-step transition made all the difference.

My Prep as a Mom (and SLP)

The night before and the morning of his first day, we read a couple of books about starting school. Talking about the routines and the feelings ahead of time (“front loading”) gave him the words and confidence to face the day. Honestly, I think that preparation showed — because when I picked him up after school, he was so excited to tell me all about it. Drop-off wasn’t nearly as hard as I imagined.

The rest of the week went pretty smoothly too. He had one little hiccup on the last day (a wave of emotions hit), but overall, it was a much easier transition than I anticipated.

A Little Trick for After-School Conversations

One thing I tried this week — and it worked beautifully — was changing how I greeted him after school. Instead of peppering him with a thousand questions (“What did you do? Who did you play with? Did you eat your snack?”), I simply said:

👉 “I missed you. I love you. I’m so glad you’re home.”

That was it.

By leaving space, he offered up the details on his own. One afternoon, he started singing a new song from music class and telling me about his teacher — completely unprompted. It was such a sweet reminder that sometimes, less really is more.

(✨ Pro tip for parents: after school, keep it simple. Show love first, then let your child share at their own pace. It helps avoid the “after-school meltdown” many kids have when they’ve held it together all day.)

Looking Ahead

This week brings more routines, more learning, and even my very first PTA meeting (something I’ve secretly always looked forward to as a mom). I can’t wait to hear more of his stories, see his friendships grow, and watch him step into this new stage of life.

It’s bittersweet, yes — but it’s also so exciting. Preschool feels like a big leap, but with the right preparation, support, and love, our little ones (and us parents) can handle it. 💛

👩‍👦 Have you sent your little one off to preschool (or kindergarten) yet? I’d love to hear how that transition went for you — drop a comment below and let’s cheer each other on in this new season.