Issue #19: What My Son’s Kindergarten Year Taught Me

A lesson in trust, growth, and the magic that unfolds when we let go

I’m done having kids. But if I ever wanted more, it wouldn’t be for the newborn snuggles or to relive those early years. It would be for one more chance to soak in the magic of kindergarten.

I remember my own kindergarten year vividly. My teacher had the biggest smile and the most infectious laugh. You could hear her coming from a mile away. She wore holiday-themed sweaters, radiated joy, and gave the warmest, most enveloping hugs. I can still hear her thick Southern accent as she called me “Miss Amelia,” and I remember the cozy, cared for feeling I had in her classroom every day. She was the best.

My daughter’s kindergarten year happened during the pandemic. The magic was there, but it felt muted. Masks, outdoor only playdates, minimal birthday parties, and ever changing COVID restrictions made everything feel a little dimmer. It was special simply because it happened in person, and thankfully she got through it with flying colors, but it wasn’t the year I’d envisioned for her.

So when my son joined my daughter’s elementary school this year, I saw it as a do-over. I was thrilled to finally have my kids at the same school. I pictured them riding the bus together, my daughter taking my son under her wing, helping him find his way at their little gem of a school.

Then, in August, we got the note: his assigned teacher had unexpectedly left. Her replacement was a teacher who had completed the teaching internship program but had never taught kindergarten or had her own class.

Like many parents in our grade, I wasn’t thrilled.

My son thrives under the care of a steady, confident leader. I worried (and wondered) how would a brand new teacher manage the curriculum, the logistics, and a room full of kindergartners? I let my anxiety take the wheel. I emailed the school. I asked for him to be moved to the other kindergarten classroom.

The school did exactly what they needed to do: they said no. It ended up being the best gift for all of us, and a lesson I’ll carry with me through the rest of my parenting journey.

The school told me they believed in the new teacher. More importantly, they showed me they believed in my son. In that moment, I needed to hear both. They reassured me the teacher could handle whatever came her way. I realized the same was true for him.

I remember the moment I exhaled and felt that first wave of confidence that everything was going to be okay.

Our school holds check-in calls with families during the second week. When I logged on with his teacher, Ms. P, I immediately felt the shift in myself.

She didn’t just know my son—she understood him. She lit up when she spoke about him, describing his caring, sensitive nature, his academic curiosity, and his sense of humor. She already saw him and shared a genuine excitement about the year ahead.

In just one week, she gave the impression not only of a seasoned teacher, but of someone who cared deeply. And in that moment, I finally believed he was exactly where he was meant to be.

I could write an entire essay about Ms. P. She rose to the occasion and so did my son. He had the confident leader I was so worried he’d miss, and he seamlessly adjusted to a new school, a new teacher, and a new classroom of friends.

She has been everything my son needed this year—and more.

This year gave me what I didn’t know I needed: a reminder that things don’t have to go according to plan to turn out well.

I thought I was advocating for my son by trying to control the outcome. But the real gift was learning to trust. Trust the school. Trust the teacher. Trust my child. That hasn’t always come easily to me, especially when my instinct is to protect and preempt. But when we step back and allow space for the unexpected, we sometimes make room for something even better.

If you’re entering a season of transition, remember that our kids are more resilient than we think. And sometimes, the people we worry might not be ready end up being the ones who show up with the most heart.

As I watched my son confidently walk across the stage to receive his kindergarten diploma earlier this month, I felt so much pride—not just for him and the wonderful year he had, but for Ms. P, for all she learned in her first kindergarten year too, and for the lessons I learned alongside them both.

We don’t always get to orchestrate the outcome. But we do get to stay open. We get to watch. And when we do, we might just witness something really special.

P.S. If your child is in the summer between preschool and kindergarten and you’re feeling a little anxious, you’re not alone. Here’s a bit of encouragement:

This season can feel like you have one foot in the little years and the other stepping into the big kid stage. It’s okay to feel all of it: the nerves, the nostalgia, the pride, the uncertainty. I know I did… with both of my kids!

Here’s my take: your child doesn’t need to be “ready” in every way. When my daughter was entering kindergarten, I anxiously spent time focusing on reading skills. But looking back, that wasn’t necessary.

What helped more than anything was laying a strong foundation. Read together. Go to the beach, the park, the library. Make art. Encourage independent play. Rest. Just be together. Connection to family sets them up for success more than you might realize.

Trust that they’ll rise to meet what’s next—maybe not on the first day, maybe not all at once, but in their own time. And trust that you will too!

If your child is starting at a new school this fall, here are a few things that helped my son with the transition. :

1. Normalize the nerves.

We talked a lot about how it’s totally okay to feel nervous before something new. I shared stories about times I felt the same way and how those feelings always eventually pass.

2. Visit the school ahead of time.

We walked through his classroom, explored the playground, and got to meet his teacher. He saw where to hang his backpack, where the bathroom was, and which seat was his. It gave him something to look forward to when the first day of school finally arrived!

3. Print out photos of the teachers.

In August, I printed out photos of his teachers along with a few other grown-ups he’d see at school: like the receptionist, school nurse, and head of lower school. I pinned them to a bulletin board near the playroom. He checked it often in the final weeks of summer, and it helped make those new faces feel more familiar.

4. Plan a playdate!

Set up a playdate with a new classmate before school starts. Even just an hour at the park can help your child walk into the first day knowing one familiar face. It makes a big difference!

Rose:

Amelia - My kids had two days of camp this week, and I managed to check a few things off the list—but what’s really made a difference in my productivity has been waking up really early. I’ve been able to plug away with no distractions.

A few other bright spots: a fun Father’s Day on Sunday, reading the new issue of Cherry Bombe magazine while the kids played at the playground (and dog-earing a few recipes I want to try—like the corn pasta and tomato toast!), and putting myself to bed early!

Liz - It’s our first week of summer break and no camps yet so we’ve embraced the free-for-all, nostalgia-inspired approach…. aka lots of pool time, play dates that last for hours, endless hot dogs, popsicles and more. It’s been lovely to have nothing to rush out to in the morning; I’ve enjoyed sipping my coffee a bit longer as boys read (and bicker ha). It’s just been really, really nice to have a slower pace after the whirlwind of end of school.

Thorn:

Amelia - It’s been a week. My husband has been abroad and I actually re-read our solo parenting post (which really resonated with our community!). One child vomited in the middle of the night on Tuesday. That same child now has poison ivy all over her face. Helllllllp. I am very ready for the weekend.

Liz - No camps meant leisurely summer days but it also meant summer exhaustion; it felt like I lived 10 years each day. We started early (sweet middle son, please sleep past 6am), and we did a lot each day, from household chores and so.much.laundry, to several pool dips all day, crafts, cleaning, reading, and more. Not to mention extra doses of sibling issues and THE WHINING…. I do not think I sat down to catch my breath each day until post kids’ bedtime, barely keeping my eyes open to read. (Amelia: the phrase *summer exhaustion* is so spot on! I’m right there with you.)

Bud:

Amelia - Keeping my bud simple. I’m so happy Mike will be home this weekend. I’m even more excited to celebrate our anniversary with dinner at one of our favorite spots, Talulla in Cambridge. We’ve all missed him, and I’m looking forward to leaning into some good family time. (Liz: Happy, happy anniversary you too xo)

Liz - All three of my boys are in day camps next week aka Mama will hopefully get a major productive week between work to-do’s, house projects and more! But before that, we may try to scoot up to Maine for a little lakeside weekend getaway and I’m really excited to introduce my boys to a special place and a little change of scenery.

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