When they’re ready for school and you’re quietly falling apart

The night before the first day of school was quieter than I expect.

 

The backpacks were packed.

The clothes were laid out.

The house hummed with a strange stillness that didn’t exist the day before.



My youngest was ready.

I could see it in his confidence, his curiosity, and the way he talked about tomorrow.

 

Yet, I felt broken. Seeing my oldest go off to school just left a lump in my throat, but knowing my youngest was moving on left me feeling undone. 

 

Because the first day of school isn’t just a milestone for kids.

It’s a reckoning for parents. 

The first day of school emotions parents rarely name…

When people talk about the first day of school emotions for parents, they usually focus on nerves or excitement.

 

What they don’t talk about is the grief.

Not dramatic grief, quiet grief.

The kind that sits in your chest as you realize a version of your life has ended.

 

Sending your child to school means releasing a chapter where you were needed constantly…physically, emotionally, invisibly.

 

And even when you’re proud…even when you know this is good…it can still hurt.

 

That doesn’t mean you’re struggling to let go, it just means you’re paying attention.

When your child is ready and you’re not…

One of the hardest parenting transitions is realizing that your child’s readiness doesn’t automatically mean yours.

 

They walk into the classroom holding their backpack tightly.

You stand behind them holding years of memories just as tightly.

 

This is the paradox of sending your child to school:

  • They gain independence

  • You practice release

 

You can celebrate who they’re becoming while missing who they were.

Both emotions are allowed to exist in the same moment.

Why parenting transitions feel so heavy…

The first day of kindergarten (or any new school year) has a way of reminding us how fast time moves.

 

In the rush of daily life, it’s easy to forget that childhood is fleeting. Then suddenly, a milestone arrives and makes it impossible to ignore. It just makes me want to yell a big “Shut the eff up. I’m not ready for it!”

 

Anyone who’s been there knows these parenting transitions aren’t just about logistics.

They’re about identity.

They’re about attachment.

They’re about learning how to stay connected - when suddenly your visibility into their day drops - without holding too tightly.

 

And those moments, despite how disruptive, deserve to be honored, not rushed past.

I wrote Wally’s First Day of School because I fully felt the transition…

So I wrote a children’s book - Wally’s First Day of School - because I couldn’t find anything else that acknowledged the parent’s experience. And like me, I bet it’s pulling you in ways you never anticipated. 

 

This isn’t only a story about a child starting school.

It’s a reflection of the quiet emotions parents carry:

  • The lump in your throat at drop-off

  • The silence of the house afterward

  • The realization that your child doesn’t need you in quite the same way anymore

 

My words names what so many parents feel but rarely say out loud and offers reassurance that love doesn’t disappear just because the physical distance grows.

If if this moment feels heavier than you expected…

So if you’re feeling emotional about your child starting school - even if you didn’t expect to -there is nothing wrong with you.

 

You’re not too attached.

You’re not failing to let go.

You’re just experiencing one of the most human parts of motherhood.

 

Life always asks something of us, and watching our children grow is no different. 

 

So If you’re navigating big feelings around letting go as a parent…

If you want language for emotions that feel hard to explain…

If you want a way to honor this milestone instead of minimizing it…

 

Wally’s First Day of School was written for you, too. While intended to be read to kids, it will speak straight to your heart. 

 

Grab a tissue and purchase it here on Amazon:

Wally’s First Day of School

 

The days are long.

The years are short.

And loving them through every transition is part of the work we never see coming.

I see you, friend.

Thanks in advanced for spreading my work to support parents everywhere. 

Wally's first day of school

Illustrated by Kimberly Roberts

I'm Courtney

I am the founder of Working Moms Movement. I’m also a wife and mom of two boys, a former culture and organizational change executive, an avid traveler, and a lover of sparkling wine.


I help working moms go from stretched thin and stuck in their to-do list to in control and fully present for what matters in their career, family, and wellbeing. Most of my work lives at the intersection of burnout, boundaries, and sustainable performance, because life shouldn’t require running on empty to hold it all together.


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