A Letter to My Daughter on Her First Day of Kindergarten

A few years ago, I heard Jenna Kutcher share that she keeps a running Google Doc for each of her kids. A living time capsule of memories, little notes, and messages that they’ll be able to read when they’re older. I loved that idea. I don’t keep up with mine as much as I wish, but I realized this space is the perfect place to implant some permanent messages for my children as well.

This blog has always been a place where I share my thoughts, help others, and sometimes just vent to the world. But I also want it to be a place where my children can look back and see exactly what their mom was doing, thinking, feeling, and saying during different seasons of life.

This post is one of those messages. A moment in time that I hope my daughter, Olive, will someday read and remember this sweet stage. The last summer before kindergarten, the season when she was still little but already so big in so many ways.

So today’s post is for my favorite 5-year-old. My soon-to-be Kindergartener. I cried writing it, I’ll cry every time I read it, and I’ll cry next week on the first day of school. Happy tears though. Proud ones.

Dear Olive,

This summer is slipping through my fingers, and I find myself holding on to every little moment with you. Not in the way I did when you were a baby, afraid to blink and miss something, but in a deeper, more intentional way. I’m soaking up the sound of your laugh, the way you bike down the road, the sparkle in your eyes when you tell me about something new you’ve learned. Because I know this chapter we’re about to step into is a special one.

Five years ago, we didn’t know what your future would look like. After your perinatal stroke, you couldn’t use your right arm or hand, and there were so many unknowns. But you, my strong, determined girl, showed us what resilience looks like. You worked so hard, you overcame obstacles most people never have to face, and you did it with a spirit that inspires me every single day. Now you play, run, climb, ski, and bike like you were born to do it. You amaze me.

This is such an exciting season for you, and honestly, I’m not sure which has you more thrilled: the fact that Taylor Swift’s new album drops soon, or the fact that you’re about to start Kindergarten. In just one week, you’ll walk into your new classroom, backpack on, ready to take on the world. I’ll want to pull your teachers aside and explain that sometimes certain things are harder for you, that you might need an extra moment here and there. But I can already see the confident grin you’d give me and hear you say, “I got this, Mom.” And you do.

I love that about you. I love that you approach life with both courage and kindness. That you are strong and sensitive, caring and curious. I love watching you make new friends, learn new skills, and tackle challenges head-on. I’ve never been much of a “baby stage” mom. You were an adorable baby, but I REALLY love this age, where we can have real conversations, where I can watch you grow not just in size, but in spirit. I can see you forming opinions, standing up for yourself, and growing confidence.

I know I’ll want to freeze this chapter. This next few years will be special. You’re still little enough to need and love me, to slip your hand in mine, to curl up next to me at the end of the day. But you’re also becoming your own person; independent, confident, and uniquely you. And that balance is beautiful.

Olive, I am so proud of you. Proud of the hard work you’ve put into every milestone. Proud of your heart. Proud of the way you move through the world. This year will bring new challenges, new adventures, and new opportunities to shine. And I can’t wait to watch you bloom.

I love you more than I ever knew was possible. Thank you for making me a mom, and for teaching me what strength, joy, and love truly look like.

You’ve got this,

Mom