For the Kindergarten Moms: The Quiet Grief of Milestones & Why Every New Phase Brings Up Old Feelings

If you’ve been on social media lately, you’ve probably seen the flood of back-to-school pictures - little backpacks, new sneakers (that you know will only stay clean for a week), and parents holding back tears behind the camera. A lot of my friends are sending their kids to kindergarten right now, and it’s been really cool (and honestly, moving) to see the range of emotions they’re carrying. Some are sad to close the toddler chapter, some are excited to see what school will bring, many are at least a little bit worried, and just about everyone is proud.

As a therapist, I’ve noticed how milestones like this often stir up more than just “my baby is going to kindergarten.” These moments become mirrors. They bring up memories of our own past, highlight the tenderness of the present, and bring up the unknowns of the future. They can feel so much bigger than one simple day or one quick drop-off because they bring up emotions that are so complex.

Why It Feels Bittersweet

1. Closing one chapter means letting go of another.

Sending your child off to kindergarten isn’t just about the excitement of them starting something new. It’s also about the quiet ending of what came before. Nap times, endless snacks, park dates, afternoons at home - all the pieces of the toddler years that shaped your daily rhythm begin to fade. Even if you didn’t always love those exhausting days (which is totally valid), it’s normal to grieve the closing of that chapter.

2. Their world gets bigger...and you have less control.

Part of the bittersweetness is realizing that your child will now be shaped by influences outside of your home. Teachers, peers, and school experiences will impact them in ways you can’t always anticipate. For many moms, this feels like both a thrill (seeing your child blossom in new ways) and a loss (realizing you can’t protect them from every disappointment or challenge). That push and pull - excitement and fear - can leave you feeling emotionally stretched thin.

3. Nostalgia sneaks in.

Milestones almost always activate our own memories. Seeing your child walk into a classroom can pull you back to the first time you did the same, or remembering when your own parents took you to school on your first day. If school was a joyful place for you, it can be heartwarming to imagine them having similar experiences. But if school was complicated, those old wounds might resurface unexpectedly. This is one of the reasons transitions can feel heavier than we expect. They stir up unfinished emotional business from the past.

4. Pride always comes with a pinch of grief.

Watching your child grow and take these big steps is a source of pride. But pride often travels with grief over the little years you can’t get back. You might find yourself staring at old baby pictures or wondering where the time went. Both emotions are true, both can exist together, and neither cancels the other out.

Why Old Feelings Resurface

One of the most powerful things to understand is that transitions don’t just trigger emotions about the present moment. They also open the door to older, buried feelings: your own childhood memories, your relationship with your parents, even questions about identity, i.e. “Who am I now that my child is moving into this next stage?".

This is why milestones can feel so layered. They aren’t just about your child - they’re also about you. About how you’re changing, how your role is shifting, and how you’re processing the passage of time in your own life.

What You Can Remind Yourself

If you’re in this season, know that it’s normal to feel pulled in opposite directions. Excited and sad. Proud and worried. Nostalgic and hopeful. Milestones are bittersweet because they touch every corner of your identity as a mom.

So the next time you feel the sting of quiet or unexpected grief, pause and remind yourself:

“This is what love feels like. It grows, it stretches, it aches, and it celebrates, all at once.”

It’s not a sign you’re doing something wrong. It’s a sign that you care deeply. And that layered, complex love is exactly what will carry you (and your child) through every new chapter ahead.

P.S. A special shoutout to my sisters and best friends who are sending their kids off to school - whether it’s the first time or the fourth. Watching you walk through the mix of emotions with honesty and courage inspires me for my own days ahead. Truly, I couldn’t ask for better teachers than you!

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Greta Strickland, MS 

Licensed Professional Counselor  

Greta has managed her own private practice in Blue Springs, MO since 2015 providing therapy to high-achieving women who struggle with anxiety and perfectionism. When she's not working, you can find Greta watching Big Brother with her husband, singing made up songs to her daughters, and sneaking "people food" to their golden retriever.