I’m Not Quite Ready for Kindergarten

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When Oliver came into the world, he had this enchanting aura about him, almost like a miniature wise wizard or a charming forest creature. His expressive eyes and serene demeanor—at least for an infant—were a bit unnerving at first. It felt like he was silently judging my every move. I remember my dad looking at him and saying that before I knew it, I’d be shopping for a backpack. Honestly, I thought I might not last that long; I feared sleep deprivation would take me down before I could even think about school supplies.

Fast forward to a few days ago when that bright orange camo backpack and matching lunch box showed up at our doorstep. I’m still here, and so is Oliver.

Since he was just 12 weeks old, he’s been going to daycare. On his first day, I didn’t shed a tear. I’ve left him with grandparents, for playdates, and at camps for hours—even days. With our recent move and all the travels, we’ve gotten pretty good at the whole hello-goodbye routine. We’re used to new teachers and fresh schedules.

But for some reason, the thought of kindergarten is hitting me differently. Our daily routine won’t change much. Mornings will still begin with breakfast, lunches will be packed, and then it’s off to school for Oliver while I tackle my work at home. Yet, as the first day looms closer, it feels surreal.

I scroll through my friends’ social media posts of their little ones starting school. I chat with other moms and know that everyone navigates that first day. Ultimately, we want our kids to thrive, to learn, and to make new friends. And how incredible it will be when Oliver can read a book! Yet, I feel like I’m losing something precious—time, especially. If the last five and a half years flew by, how fast will the next thirteen go? Can I keep pace? Will I be able to stay engaged in his life?

Looking back, I have no regrets about our journey so far. We’ve shared wonderful moments, even amidst the tough times. We’ve enjoyed cuddles, cozy naps, and sun-soaked afternoons at the park. I don’t wish I had done things differently; we’ve navigated our path in a messy but joyful way.

As kindergarten approaches, I find myself wishing I had a reservoir of wisdom to draw from. It often feels like I’m sprinting to catch up, constantly facing new challenges. Just when I think I’ve got a handle on one thing, another pops up. In a single day, I’m explaining everything from the purpose of certain body parts to why the sky is blue, and why we shouldn’t call people “poopy heads.” It’s a whirlwind of questions, and by day’s end, I’m left wondering if I fumbled any of my answers.

With the complexities of school on the horizon—bullying, homework, and sports—I feel the pressure. The questions are getting tougher, and I really want to do right by him. Kindergarten feels like a significant milestone; its impact will echo throughout his life.

Maybe that’s why this transition feels so daunting—it’s like a test of everything I’ve done so far. Will he adapt? Will he form friendships? Have I given him the love and support he needs? Will school enhance his foundation or undermine it?

I remind myself that in a couple of weeks, we’ll settle into our new routine, and it will likely feel second nature. Just like how we forget the pain of childbirth or the exact moment our little one first smiled, I’ll eventually forget the sweet days of preschool.

It’s hard to comprehend how this tiny being, once just goo in an orange cup, has transformed into a spirited boy who can break boards at Taekwondo and has strong opinions about his backpack color. I can’t pinpoint whether it’s my doing, a stroke of luck, or a little bit of both.

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Summary

The journey of preparing for kindergarten is filled with mixed emotions for parents. As children grow, so does the complexity of parenting. This piece reflects on the bittersweet nature of transitions, the memories made, and the hopes for the future, all while navigating the challenges of raising a child.