The Bittersweet Goodbye to Elementary School: A Mom’s Honest Emotions as Her Daughter Starts Middle School

I didn’t have a Fifth Grade Graduation. Thirty years ago, we wrapped up elementary school with a field trip to the middle school and a picnic lunch. There was no pomp, no certificates, no “promotion” signs in the yard—just a quiet shift into the next chapter. Somewhere along the way, things changed. Fifth grade became a milestone worth celebrating. And now, here I am, getting ready to say goodbye to elementary school… wondering how we got here so fast.

Reflecting on Her Elementary School Years

From the very first day of fifth grade, my fellow parents and I have been carrying a swirl of emotions. We all knew this year—your final year of elementary school—would mark the closing of a long and meaningful chapter. Elementary school is where you planted your roots. You were safe, supported, and steadily growing into the person you’re becoming. You learned how to be a learner. Your classroom felt like a home away from home, and your friends and teachers became like a second family.

Why This Goodbye to Elementary School Feels So Big

In typical Caitlin fashion, I saved all of my emotions for the last week of school. It’s hard to put into words what I’m feeling—because it’s not just sadness or pride or fear. It’s all of it, tangled together. I know my little bird is ready to fly. But middle school is a whole new world. It’s the start of something bigger: a season of self-discovery, independence, and transformation. And I’ll be here, watching and cheering, every step of the way.

A Letter to My Daughter on Fifth Grade Graduation

Dear Annabelle,

I vividly remember your nursery school orientation at Creekside Christian Academy – not just because I was extremely pregnant, worried I would miss your first day of going into labor, but because it was a BIG day. You were going to a nursery school, not just baby school daycare. As my tiny two-year-old clung to me, resting her hand on my round belly where her sister grew, I feared our first day goodbyes would be tough. But you surprised me, running off excitedly. You never saw my tears, only my smiles. And we were all so proud of your bravery and enthusiasm for a new adventure.

Fast forward to your first day of Kindergarten. Elementary school is the real deal and admittedly, I was scared. With so many outside influences awaiting my daughter I worried I would not be able to protect you. But you didn’t seem afraid at all—just ready, excited, and wide-eyed for whatever was next.

The first few months of Kindergarten were filled with learning and cute class parties I felt so happy to be a part of. Then, the pandemic began and halted your Kindergarten experience. Remember when we tried to do school at home? Months later, social distance screens and masks muted everything first grade was to be about. Even second grade was watered down – but your teacher did her best with an incredible energy and uplifting attitude to make it the best year possible. As a parent, it was always difficult knowing you were missing out on a regular education and childhood. But your quiet resilience and ability to adapt to a world that kept changing left me deeply impressed—and so proud.

Third grade felt like a turning point—a joyful return to something close to normal. While there were a few bumps along the way, you were once again blessed with a wonderful teacher who helped you shine, especially in your academics. My heart swelled with pride as your love for math and reading truly began to bloom. By fourth grade, the road grew a little more complicated, as it naturally does. You faced quiet challenges—both academic and social—that gently pushed you to grow. My instinct was to step in and shield you from every hardship, but I knew you needed space to navigate those hurdles on your own. And you did, with quiet strength.

Fifth grade has been your best year yet—one of incredible growth, joy, and confidence. You’ve matured in so many ways, but never let go of that special silliness that makes you, you. This year, you learned how to truly express yourself—whether it was through thoughtful conversations, powerful essays, or standing tall during public speaking presentations. Your love for learning took off, especially in math and reading, where you grew beyond what we ever imagined—off the charts, truly. You discovered a hidden talent for photography, took on leadership roles with quiet strength, and showed up as a kind, loyal friend. You handled tricky social situations with grace, ignored what’s unkind, and made space for shy friends to feel seen. You laughed, you had fun, you worked hard—and every day, you’ve made us so unbelievably proud.

As we celebrate your promotion to middle school, I find myself feeling a mix of emotions—just like I did all those years ago when you started Kindergarten. It’s bittersweet, saying goodbye to the comfort and familiarity of elementary school, and watching you step into a brand new world without me right by your side. I know you’re feeling it too—a little scared, a little sad, but also so excited. That’s the beauty of change: it stretches us in all the best ways.

Middle school will bring new challenges, new friendships, and so many opportunities to grow into the incredible young woman you’re becoming. And even when the days feel big or overwhelming, just remember—you are ready. You are capable. And no matter where you go or how tall you grow, I will always be right here, cheering you on.

A Bittersweet Ending, A Beautiful Beginning

Watching you walk across the promotion stage, I’ll be holding back tears (or maybe opening crying) —but also feeling deeply grateful. Grateful for the beautiful foundation you’ve built and for the memories we’ll carry with us. And while this goodbye to elementary school is bittersweet, it’s also the start of something extraordinary. You’re ready. We both are.

If you’re a mom facing a similar milestone, I’d love to hear your story. What are you feeling as your child closes this chapter and starts a new one? Leave a comment or share this post with someone who needs to know they’re not alone in this bittersweet moment.