What I didn’t see coming about the first day of school

I have graduated so many parenting chapters in the last three years. Big ones, like childbirth, recovery – not once but twice. Newborn-hood, teething, colds, tummy bugs, crying, whining, tantrums, toddlerhood – you name it. Everything from “I need you to do everything for me” to “I need you to let me do it myself.” Yet none of it prepared me for what is next – my son’s first day of school. 

Every period of change has been on the heels of something that makes me grow closer to my babies. On the contrary, preschool is the first chapter where my baby is growing away from me.

He took the better of two days to enter this world. When I finally held him in my arms for the first time, all of the struggle, worry and pain of labor vanished. The world abruptly paused, and we held each other so close that our heartbeats aligned – and that was really all we had to do for quite some time as we nurtured the beginnings of our relationship.

During my recovery, we didn’t have a clue what we were doing. We spent majority of our nights bouncing on a yoga ball and listening to the sound of the shower running. As exhausting as that phase was, we soon found a harmonious rhythm as he adjusted to life outside the womb and I adjusted to my new role of never-having-a-break-and-omg-parenting-is-24/7.

Once we graduated survival mode, he patiently allowed me to trial and error all kinds of parenting advice. Many laughs and snuggles were exchanged in this chapter as we learned to tune into our own unique bond.

Then we promoted him to big brother. Growing from a family of three to four rocked our foundation. The way that my daughter needed me and the way that my son needed me were polarizing in just how opposite they were (and continue to be). Both were in diapers. Both wanted me to hold them close and rock their worries away. Both wanted me to lie next to them to fall asleep. My son’s first three-word sentence was, “I want mama.” At only 19 months apart; I basically had two babies.

Then one day everything changed. His sentences grew longer and clearer. He stepped right out of diapers and into the cutest little man boxers I’ve ever seen. Rocking him on the nursery chair felt clunky and uncomfortable, and he wasn’t asking to be held nearly as often. Overnight, I had a baby and a little boy instead of two babies. School was no longer this thing in the distance, and here we were touring programs until we found the right fit and enrolled.

That’s when it hit me. I had been so focused on school being an exciting first for him that I overlooked how it would be an emotional last for me.

When I woke up to his sweet little voice at 7:30 a.m., I realized this is the last time our morning routine would be slow and steady. It’s the last time we would disregard the clock, stay in our pajamas over breakfast, and meander over to the playroom with baby sis. It’s the last time I’d take my morning coffee to the office and overhear his wooden blocks hitting the floors and baby sister giggling back at his movements.

And after he’d tired of his morning play, it’d be the last time I’d readily hear his little-big footsteps trickle over to me and tug on my pants asking for a granola bar, adorably pronounced “groy-oh-la.” Or hear him shout from the potty that he needs my help. Or see him smile ear-to-ear because he just discovered a new ability in the kitchen on his sticky step stool, fresh from that groy-oh-la bar that left a trail of crumbs, which he will want to vacuum up “all by my myself!”

It’s the last time I’d spend our afternoons, outings, errands, with both of my ducklings in tow. People would no longer strike conversation over how alike they look as I’d find myself with an empty extra hand. I will look back at their shared car-seat mirror and only have one mini-me to sing and dance with. I will scratch off the toddler story times from my weekly calendars because we’ve been demoted back to the wiggle giggle baby-only slots.

Toughen up, mama. It’s just preschool, right? I mean of course I knew this day was coming. This is the goal of parenting – we raise them so that they can leave the nest. I guess I envisioned this fleeting feeling with his first college acceptance letter. I envisioned it with his first apartment lease. I envisioned it with his first great love, maybe even as early as his first crush. I didn’t think I would feel such a kick to the gut over picking out his tiny little red backpack and bento lunchbox.

But that’s just it. Preschool is all of these things.

To nurture our babies, we hold them close. That is all I have ever done  and that’s what I’m good at. To nurture our children, we must let them go.

That is something I haven’t a clue how to do, but come his first day, I will have to find the courage.

I will send him off with his little red backpack and bento box, fighting my own tears until he’s long gone in the classroom. There, I will leave what has become my entire world in the hands of a teacher who will become the first person other than myself to wipe away his tears. And even though this isn’t as big as sending him off to college,  this is the start of that. This is when our worlds separate from one to two. This is the moment where I say goodbye to my baby forever because he will run back into my arms as a little boy – and then a teenager, a young man, a grown man.

Here on out, every first for him will be another last for me. And even though it will be my greatest joy to watch him grow, I’m not sure I will ever stop longing to hold my baby just one more time.IMG_6413


  1. Oh Jenna…. my heart…such beautiful words. It is bittersweet… and , no … each step is harder than you think … it’s a world of firsts… he is so much younger than his dad was at his first pre school. One day at a time….deep breaths…


  2. Oh my, you brought back that first walk hand in hand with my first born to his first day of school. Tears are falling now just like they did on that long walk home by myself.


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