You’ve been talking about it for months now. My sweet, oldest boy—you’re starting school this year . . . and you just can’t wait.

You bring it up daily in conversation, with a twinkle in your eye. Your sharp little mind and sensitive soul want to know just what it’ll be like, just what to expect. 

Should I raise my hand when I have something to say, Mama? 

Can I learn how to read my favorite books all by myself?

Will my teacher be nice? 

Do you think I’ll make new friends? 

You are so ready for this next chapter of your life. Of both our lives, really.

You’ve already picked out your backpack—a navy blue, Dino-covered number that you’re sure will be big enough to hold all of your things.  

You’ve planned which outfit you’ll wear on the first day and exactly what you’ll say to your teacher when you finally meet her.

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You’ve assured me that even though we’ll be apart more than ever before, I don’t have to miss you too much because you’ll still be my boy. Just a little bigger now, Mommy.

You are ecstatic—in your five years I don’t think I’ve ever seen you so excited about anything. And me? I want nothing more than to share in that excitement with you, but the truth is my mama heart is breaking. 

I just always thought it would be different. 

I thought you starting school would be a happy time. Bittersweet, yes, but a joyous milestone nonetheless.

I never imagined it would be so clouded in doubt. I never pictured your first year as one big, ominous, worry-filled question mark. 

Oh, babe . . . it all just makes me so sad. 

Now I wonder if you’ll even be able to see your teacher’s kind smile behind her mask, or if it will be hard for you to make friends from six feet away.

I’m afraid your daddy and I won’t be able to walk you through the door on your first day to help you hang your coat and backpack in your cubby. I worry you’ll cry from nerves, and I won’t be allowed to go into the classroom to comfort you. 

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I worry you’ll start school and it will be everything you’ve ever dreamed. . . only for it to shut down for a while and your heart to break at the feeling of missing out.

I’m so sad I won’t get to go on class field trips and watch your eyes light up as you experience new things, new places, and new people. I’m even sadder you may not have any field trips to begin with. 

It hurts my heart that this will be your first experience with school.

I know you won’t know any differently—but I will. I’ll know all of the things you’re missing out on, and for that, my heart breaks. 

This isn’t how I thought it would be, but I promise to stay strong for you. I promise to show you only my excitement and never the fear bubbling just under the surface. If I can be a source of positivity and comfort, I know you’ll be able to weather anything the future throws at you. 

You’re starting school this year, and you just can’t wait. 

We’ll do this together, little one. 

P.S. We love The Preschool Box, a subscription filled with books, crafts, and skill-building activities delivered right to your doorstep each month! 

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