A Letter to My Child on the First Day of Kindergarten

A Letter to my Child on the First Day of Kindergarten

INSIDE: A mom’s heartfelt letter to her firstborn child on the first day of kindergarten.

A Letter to my Child on the First Day of Kindergarten

Dear son, on your first day of kindergarten,

Everyone keeps telling you how much you’ll love school. This is very true.

Everyone keeps injecting you with mini boosts of confidence. This is very good.

But as I listen to each well-intentioned person try to drive out any fear, it’s occurred to me you might also need to hear this: It’s okay if you’re scared.

Because here’s the honest truth: Mommy is scared too.

Of what, you’re wondering?

I’m scared of being apart from you for 8 hours every day.

I’m scared of you spending too many of those hours in a chair, and too few running wild and free.

I’m scared of the 5thgraders on your bus.

I’m scared of the new words you’ll hear, the new behaviors you’ll see.

I’m scared of the boxes you might get put in, the labels you might be given, the pegs you’ll be expected to fit into.

I’m scared you’ll change.

I’m scared you’ll lose your innocence, your sweetness. I’m scared people will try to harden your edges, toughen you up.

A Letter to my Child on the First Day of Kindergarten

And I’m just going to say it: I’m scared to give up control. To lose any influence I might have had on you up to this point.

My dear son, Mommy is scared to let you go.

Clearly fear is present in my heart, and it’s normal if it’s hanging out in yours too.

But here’s the good news:

Fear is not the only story.

Right next to that clenched ball of panic in my gut is something far more powerful:


Hope for the opportunities your school will give you, ones that our little family alone cannot.

Hope for the wider diversity of kids you will get to meet—and befriend.

Hope for the chances you’ll have to show kindness to those who need it most.

Hope for the chances you’ll have to receive kindness in the moments you need it most.

Hope for the new and exciting ways your brain will be challenged.

Hope for the new and exciting ways your heart will be too.

Right now we’re sitting in the blurry place. We can kind of see what lies ahead, but the path forward is still pretty fuzzy. There is so much we don’t know about the coming weeks, months, and years.

But there is one thing we do know, without a doubt:

You are ready.

You will have to do hard things—but you will quickly see that you CAN.

No doubt some days you will come home beaming, so proud of what you did that day.

Others you will come home crying and collapsed.

Some days you will feel on top of the world.

Others you will feel utterly drained and depleted.

You are ready for all of it.

We’ve raised you to be kind and creative and empathetic—but our intention was never for you to be all of those things in a bubble. It’s time for you to take your kindness and creativity and empathy into the bigger world.

And yes, you will change. I know that. But deep down I’m happy about it. I don’t want you to remain the same—static and stuck. You will change, but I believe you will become more fully and wholly yourself.   

Gosh, that is going to be beautiful.

A Letter to my Child on the First Day of Kindergarten

So as you head to kindergarten, my precious boy, I have to let you go…a little bit.

But I’m also going to stay right here: walking beside you, crying with you, cheering for you. Loving you as fiercely as ever. Facing my fears so I can be here with you as you face yours.

Yes, Mommy is scared.

I’m scared to watch you jump because I know sometimes you’ll fall.

But without the fall, you cannot rise.

Without the jump, you cannot soar.

It’s time to see just how high you can fly.

With all my heart,


3 responses to “A Letter to My Child on the First Day of Kindergarten”

  1. What a nice letter! Thank you Katie for sharing it! I can only imagine how hard it was to let go of your son on the first day of Kindergarten because it probably felt like it was yesterday that he took his first steps or said his first words. All parents have to go through this. It’s hard but that first day of Kindergarten is the true beginning of his growth.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.