The Playground Is Harder Than the Boardroom.

Haisley starts Montessori in a few weeks, and I've spent the last several days trying to figure out why my anxiety is so much higher than I expected.

It's not because I'm worried about her. She's three. She's going to walk into that classroom wearing whatever dress she insisted on wearing that morning, find another little girl who also likes dresses, and by the end of the day she'll probably have declared someone her best friend. Kids make friendship look so easy.

I, on the other hand, feel like I missed the handbook.

For the last three years, our little family has lived in a pretty comfortable bubble. Haisley has done dance, music classes, library story times, Bonnet Springs drop-ins, birthday parties, Disney with friends, and a handful of playdates. She's been around other kids. We've been around other families. I don't feel like she's missed out.

What we haven't really had is that circle of parents you text on a random Tuesday to see if anyone wants to meet at the park.

I don't think I realized there was a difference until now.

School feels like an entirely different world. Suddenly there are class parents, peer families, volunteer opportunities, birthday party invitations, organizations I've never heard of, and somehow everyone else already seems to know everyone.

To make the transition a little easier, the school pairs every new family with a current family. Ours was paired with the mom who runs the Uniform Closet. She was one of the very first people to welcome our family, and I'd told her I was planning to stop by the Uniform Closet event.

Then I completely forgot.

I wish I could tell you there was a good reason.

There wasn't.

I had approximately 847 tabs open in my brain, and apparently the Uniform Closet was the one that crashed.

It wasn't until later that afternoon that it hit me what I'd actually done. I'd unintentionally stood up the very mom whose job was to help new families like ours feel welcome.

Excellent start, Amy.

The irony is that building relationships with strangers is literally what I do for a living.

Every week I introduce myself to people I've never met. I build trust, find common ground, negotiate contracts, and create relationships. I genuinely enjoy it.

At work.

In my personal life?

I dread it, and I think I've finally figured out why.

The preschool paradox, at least for me, is that I'm completely comfortable walking into a boardroom full of strangers, but walking onto a preschool playground where everyone already seems to know each other feels infinitely harder.

A boardroom comes with a script. I know why I'm there. I know what success looks like. I know what I'm trying to accomplish.

A preschool playground doesn't come with a script; it just asks you to belong.

And somehow that feels infinitely harder.

Our family doesn't really fit the script people expect, either. I'm the working parent. Jimmy is the stay-at-home parent. He's the one who will probably know the teachers better than I do. He'll probably be the familiar face at pickup. He'll probably end up chatting with other parents while I'm on Teams calls trying to close business.

That's the life we've intentionally built, and it works really well for our family.

What doesn't quite work is the assumption everyone—including me—still makes.

The follow-up texts come to me.

The playdate invitations come to me.

The volunteer questions come to me.

I keep finding myself replying, "Actually...Jimmy will probably be the one there."

Nobody is doing anything wrong. They're following the script our culture has written. Mom is the social parent. Mom knows everyone's names. Mom coordinates the playdates. Mom volunteers at school.

The funny part is that I've internalized that script too.

Even though our family works differently, I still catch myself feeling like I'm somehow falling short because I'm not the one who knows every parent, remembers every event, and magically plugs us into this whole new world.

I've spent the last several days wondering why this transition feels so much heavier than it probably should.

I think part of the answer has nothing to do with Montessori.

Earlier this year, I lost my best friend.

I've realized grief isn't just missing someone on birthdays, holidays, or anniversaries. It's reaching for your phone because Haisley said something hilarious. It's seeing a ridiculous Facebook post. It's laughing because your parents adopted a pit bull while your mom continues insisting it's definitely not a pit bull. It's having one of those completely ordinary moments that aren't important enough to warrant a phone call and suddenly realizing you don't know who to send the text to anymore.

I think that's the part of grief nobody prepares you for. The milestones are obvious. The ordinary Tuesdays are not.

Maybe that's why Montessori feels so much bigger than school.

Everyone keeps telling me this is where I'll find my village.

Maybe they're right.

But if I'm being completely honest, I don't think I'm looking for a village.

I think I'm grieving the fact that I used to have a person.

The person who got the random "wtf" texts. The person who already knew every character in my life, so I didn't have to spend five minutes explaining the backstory before I could tell the funny part. The person who would've been getting a steady stream of messages from me over the next few weeks saying, "I have no idea what I'm doing," and, "Tell me this gets less awkward."

Instead, I'm figuring this season out without her.

Maybe that's why this feels so overwhelming. It isn't because I don't know how to be Haisley's mom. I know how to do that.

I'm just learning how to be this version of her mom.

Maybe school won't just be where Haisley finds her people.

Maybe it'll be where I find mine.