Tomorrow: A Bittersweet Milestone

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Tomorrow, I’ll wake up before dawn, dive into my usual routine of reading, writing, and praying, and then sneak downstairs to whip up breakfast. Afterward, I’ll tiptoe back up to plant kisses on my kids’ foreheads while pointing to their chalkboard schedules.

Tomorrow, I’ll stroll down the sidewalk, fingers entwined with one child’s hand while I hold the other’s, all the while keeping an eye on the third who might lag behind or dash ahead—because, you know, only two hands to manage three boys. Tomorrow, I’ll take my sweet time walking to the school just half a mile away, where I’ll leave all three of them for the day.

A New Chapter Begins

This year, my youngest will join 125 other kindergarteners, stepping out of our comfortable home into a wider world. And despite having done this twice before, it doesn’t make it any easier. I’ll join the ranks of other kindergarten parents lingering at the door, watching my little one venture into a realm we can’t control—a world full of challenges that can be daunting and heartbreaking.

Yes, tensions have risen at home as we approached this day, and my partner and I have exchanged glances that say, “Can we just get this school thing started already?” But deep down, I don’t mean it, not really. The start of school signifies their absence—away from my encouragement, from my watchful eye, and from my protective bubble. They’ll never be away from my love, of course.

Emotional Goodbyes

Today, my three kids have climbed into my lap multiple times, as if they sense the significance of this last day together. Their little hugs scream, “We can’t go! I can’t let you go!” What if they struggle to make friends? What if they clash with their teacher? What if the outside world shatters their spirit or confidence, or even worse, their hearts?

Tonight, I’ll wander through our home’s hallways, brushing my fingers over their backpacks hanging on hooks. I’ll peek into their rooms to see their sleeping faces—so big yet so small—and I’ll cry, praying for a good year ahead. I hope they understand just how capable they are of navigating life’s turbulent waters, and that they truly grasp their importance to me, to their friends, and to the world.

The Journey of Letting Go

I can preach this to them every single day, but they must learn it for themselves—out there, away from home. I know this, yet letting go isn’t quite so simple. I recognize the pain of loss and don’t want that for my boys. I know what it feels like to be defeated or to face cruelty, and I wish to shield them from that.

Sure, it sounds absurd because it’s part of growing up—the heartaches, the disappointments. Don’t I want them to thrive? Don’t I want them to be their own people? Of course, I do. But it’s also hard to forget just yesterday when they were tiny, needing me for everything—holding their hands as they took their first shaky steps, bathing them, pouring their milk, and tucking them in.

Where did the time vanish? Where did my babies go? Now, they’re just tall, lanky kids eager to embrace this new adventure, while I’m left grieving. What do I do with this sadness? I’ll break down just outside their rooms, listening to their breaths in a slumber that feels distant.

A New Adventure Awaits

This is just one of many steps—an ongoing journey, I know. Yet it feels abrupt, as if we had no time to prepare for this leap into independence. Tomorrow, I’ll guide them into this new chapter, leaving them in a space where they’ll discover kindness and cruelty, where they’ll witness peers choosing cookies over their lunches if they feel like it.

Tomorrow, we’ll pause outside the school doors for a thousand pictures, and they’ll beam with pride while I quietly weep—because underneath it all, they’re still my babies. As we enter their classrooms, two of them will be seasoned pros, while one will pause, looking back with those big eyes that silently ask, “Are you certain?” My heart will scream, “Yes, sweetie. I’m sure.”

But I’m not. He’s ready to spread his wings and explore the world outside of me. It aches because I remember cradling him through sleepless nights and cheering him on as he mastered the stairs. I still stand at the bottom, arms outstretched, hoping for the best, but ready to catch him if he falls.

Embracing Change

So I’ll let him go. I’ll allow him to step into that classroom, greet his teacher (even if he can’t recall her name yet), and I’ll leave him there. My partner will squeeze my hand, understanding the turmoil inside me, and we’ll head home with the younger ones, who fill our house with noise, leaving me feeling a bit empty.

I’m letting him go because I know he’s ready to test those wings we’ve helped build. He may stumble and fall, but he’ll rise stronger each time. He’ll discover friendships, learn the best games, and love his teacher. He’ll be just fine.

Because he is stronger than I realize, braver than I can imagine, and entirely capable. Tonight, I’ll tiptoe into his room for one last glance, one last touch, one last kiss on those long lashes that only feel my lips in his dreams. Then I’ll retreat to my own room, where the night will draw the covers over my heavy heart.

A Pivotal Moment

Tomorrow marks a pivotal moment. My boy will take flight for the first time, and I’ll be there, always watching, with tears of pride and a heart full of hope.

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In summary, this piece captures the bittersweet emotions of a parent letting go as their child embarks on a significant milestone—starting kindergarten. It reflects on the struggles of balancing love and independence, the fears of the unknown, and the inevitable growth that comes with each step away from home.

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