Articles & Guides
What can we help you find?

Nope, nothing is going to prepare me for my son’s first day of kindergarten

My son is ready for this kindergarten milestone, but I am already crying tears tinged with the bittersweet passage of time.

Nope, nothing is going to prepare me for my son’s first day of kindergarten

At the beginning of the summer, while swimming in the pool and attempting to sneakily splash his grandpa, my little one realized that he could extend his legs and actually stand with his feet planted on the floor of the shallow end. Excitement ensued, but as I caught my mom’s eye, I realized that she knew exactly what I was thinking and what I was feeling. She promptly reminded me to take this moment as a metaphor and carry it with me as he puts one foot in front of the other and walks into his first day of kindergarten. 

Because when he walks in — whether it be with the force of a crashing wave or with some first-day trepidation on his tippy-toes — he will be standing on his own … in a new school, with new friends, welcoming new experiences and armed with all the tools he needs to keep his head above water. He is, I believe, prepared for this moment, aware of all the feelings that accompany the new — the sadness of leaving one experience and the joyful anticipation of starting another, the apprehension and the enthusiasm. I, on the other hand, will be left swimming in a puddle of tears, both the happy tears that come with parental pride and those that are tinged with the bittersweet passage of time. 

On big new childhood beginnings

Sure, on the surface, my son and I are seemingly well prepared for this first day milestone. We’ve picked out a new backpack and lunch bag. We are finalizing schedules. We’re meeting new classmates. We may no longer need to sing “Grownups Come Back” (thank you, Daniel Tiger) to usher in a new school year, but my husband and I are answering his questions about kindergarten with our own relatable experiences. We are also, of course, joining my son as he reminisces about his early school days and asks to see photos and videos from when he was a baby — because clearly the sentimental apple doesn’t fall far from the tree. 

And, above all, while I am excited for him as he begins this new adventure, I am being careful not to project my own emotional unreadiness — or at least I am trying not to. 

I thought that perhaps these feelings were amplified for me: I am a mom of one who has been blissfully home with my baby and best buddy — he is a seriously smart, fun and clever conversationalist whose company I adore — since his birth. I’ve savored both the milestones and everyday moments — every snuggle he’s needed with his hand held over my heart to fall asleep, every walk we’ve taken holding hands down the block to and from school, every game of make-believe we play, every story he now reads to me, every silly song we sing and every dance we dance, every hug and “I love you,” every observation and insightful question he asks (he is never at a loss for words) that opens new worlds for him and opens my eyes to the magic and wonder in which he sees it.

“As I talk to other parents, both those who are anticipating their own first day cry when they wave goodbye in the school playground and those who have already experienced breaking down into waterworks when the bus pulled away, I’ve found that, on some level, this feeling is quite ubiquitous. Whether they admit it or not, most parents get sentimental when letting their littles venture a bit farther from the nest.”

Over the years, we gradually eased into longer and more frequent days of preschool, more afterschool activities and more supervised playdates. But still, so many school dismissals were met with my son beaming and brimming with detailed stories about his day, yet excited for “Mommy time” (something that was seemingly infinite when he was a baby and for months of pandemic life).

I have felt that these years, from the quiet cuddly newborn days to the amazing transformation from infant to toddler to preschooler, have passed in the blink of an eye. In fact, I burst into tears at kindergarten orientation when an administrator said that the years start — start?! — flying by once children enter grade school. 

But as I talk to other parents, both those who are anticipating their own first day cry when they wave goodbye in the school playground and those who have already experienced breaking down into waterworks when the bus pulled away, I’ve found that, on some level, this feeling is quite ubiquitous. Whether they admit it or not, most parents get sentimental when letting their littles venture a bit farther from the nest. (And, yes, sentimental apples, like myself, can still savor that first uninterrupted coffee of the school year.) I am just grateful that my son will still give me a hug goodbye and (hopefully) not be embarrassed by my tears should I not be able to hold them back. I guess I have plenty of time to practice that restraint before his first day of college.

A major milestone for them — and us

You see, we often forget that while kindergarten is a milestone for our children, it is a major milestone for us as parents, as well. It is a transition that we are ready to help our kids through, but aren’t quite prepared for ourselves. And, no matter what that transition looks like (perhaps it involves the first time solo on a school bus or simply moving to a bigger kid part of the building), as we tell our children, transitions. Are. Hard. 

I am preparing myself for the eventual feeling of, as my mom always says, “bigger kids, bigger problems” — as in problems that may occur when their world starts expanding beyond our immediate control. In reality, the first year of elementary school might not be all that different from pre-K, but it is a transition that feels big. Perhaps it is because both literally and symbolically my son’s world is getting bigger. He will be in a bigger school with bigger kids for more hours with more responsibilities. And, yes, there will be more hours during which I will miss him and how he always makes me smile with his incredible comedic timing. 

There will be both amazing firsts and inevitable disappointments — ones I hope I am prepared to help him through with the same confidence and unconditional love that has helped him master his milestones and take on his world with a loving, kind, creative and charismatic personality. My son recently acknowledged that he doesn’t always need my help but loves when I help him — and perhaps just knowing this will eventually help me through this particular moment of letting go. 

“I often say that letting go has always been the hardest part of parenthood. It’s a part that no one really prepares us for — even though it tugs at our heartstrings early and often.”

All about letting go … even just a little 

I often say that letting go has always been the hardest part of parenthood. It’s a part that no one really prepares us for — even though it tugs at our heartstrings early and often. It’s the wistful anticipation of that last nursing session or bottle. It’s bidding a final farewell to the shelf of unused “just-in-case” diapers or transitioning from a crib to a big kid bed. It’s, for me, leaving my then toddler for the first day of preschool separation nearly three years ago and nervously sitting at a coffee shop around the corner and crying. It’s stepping back so that preschoolers can use the skills they’ve learned to figure out how to share a toy or take turns on the slide. It’s hearing my baby say “yellow” and not “lallow” and becoming nostalgic for every adorable turn of phrase while in awe of the maturity and humor he so often exudes.It’s the overwhelming emotion at pre-K graduation that has us marveling at both our children’s accomplishments and our own as parents — while shedding tears about this chapter coming to a close.

I am grateful to be able to really live in each of these  moments as a parent, but as today turns to yesterday and I immerse myself in each new fabulous stage of my son’s childhood, I selfishly want to experience and reexperience it all — the yesterday and the today — all at once. My baby is now 5 — a whole hand — and I want to keep holding his hand tight (and in many ways I always will), but I know that I will also need to eventually prepare myself, over time, for the letting go that accompanies watching our children grow and soar.

Of course, perhaps if we don’t think about it as truly letting go, but rather building upon previous chapters in a continuous book, the letting go might just get easier. Knowing that we can revisit old chapters while realizing how lucky we are to be able to write new ones makes it all a fluid journey held together by the natural progression of time. 

Right now, though, all of those literal baby steps, those momentous milestones, have led to one that begs for that much more independence. It is one that is begging me to remember that my baby can, indeed, stand on his own, even if it is — for now — in the shallow end. Even if I am not quite ready for it on the first day of kindergarten.