Charlie Started School — Here's How It's Going
Three weeks in, one permanent lateness record, and a few things that are actually working
Let’s start with the most important thing, because mom guilt is real and I want to get ahead of it: we were right.
Sending Charlie to school full time was 100% the right decision — for him, for us, for this season of our lives. He is thriving. And I’m going to keep saying that out loud, because I think it needs to be said before anything else.
Three weeks in and I obviously think I’m an expert. If you know me at all, you know this tracks — I have always had very strong opinions, very quickly. Loosely held, but loud. Catch me in six months and we’ll see if any of this still holds. But in the meantime, we’ve learned some things, and if you’re about to make this transition yourself, maybe some of it is useful.
Drop-Offs
Drop-offs were rough. Charlie was hysterical — full crying, real tears, the kind that make you want to peel him off the teacher and take him home and never leave the house again. I was not prepared for what that actually looked like in practice.
Here’s something about Charlie’s school that jarred me at first and that I now think is one of the most important things that I didn’t fully understand until I was standing on the wrong side of that door: caregivers, parents, nannies, whoever your designated person is — are not allowed to cross the threshold of the classroom door. Full stop. That’s the rule.
So when Charlie was hysterical in week one, when he was crying and screaming and genuinely devastated, I had to push him through the door, hand him to the teacher, and walk away. I could not go in. I could not console him. I stood on the other side of the door and I left. Drop-off happens outside the classroom door — pushing him across the threshold and into his teacher’s arms. It was genuinely heart-wrenching.
According to the teachers, it took five to ten minutes to calm him down each morning that first week. His teacher told us that standing by the window, looking outside, and singing songs helped him regulate. And that once they got through that initial wave of screaming and tears, he was genuinely great for the rest of the day. Playing, exploring, greeting every single friend who walked through the door like a tiny social chairman.
The philosophy behind it — and I’ve come to believe in it completely — is that the classroom belongs to the kids and the teachers. It’s their space, their safe place. It wouldn’t be fair, especially to two-year-olds, for one child to have their parent come in and console them while no one else does. And at this age, out of sight really is out of mind. The moment I’m gone, he resets. The teacher is there. His friends are there. He’s okay.
Three weeks in, drop-offs are finally getting better. Not perfect, but better. And that trajectory matters. There are still mornings where he shows a little hesitation at the threshold — a pause before he crosses it — but no more screaming and no more tears. I actually think that pause is meaningful. That doorway has become a real physical boundary that he understands in a way I don’t think he would if I’d been walking in and out of it for three weeks. He knows what it means. This side, and that side.
I’m proud of him for crossing it. Every single morning.
Drop-Off Is at 8:30 — What That Actually Means Is 8:20
On our first day, I arrived at 8:30 on the dot. Proud of myself. On time. Very together.
Charlie did not cross the threshold of the classroom door until 8:39. I knocked at 8:30. It still counted as 9 minutes late. Those 9 minutes live in Transparent Classroom — the app the school uses for daily updates, nap times, meals, the works. I need you to notice that “transparent” contains “parent.” As a communicator, I am obsessed. It also logs every arrival time, which is how I know those 9 minutes are permanently on the record. There is, to my knowledge, no actual penalty. But that is marked in a record that I see daily — we have not been late since.
This now means we leave the house by 8:00am. Every morning. Which, for context: our old routine involved Charlie still being in pajamas at 8:00am, eating breakfast at his leisure. That was our life. That was the rhythm. School replaced that entirely.
This is a complete overhaul. For Charlie and especially for me — a working mom who commutes into the city and has not had to be out the door by 8am since she was a 22-year-old financial communications analyst. I am, let’s say, meaningfully older than that now.
What I Do Before He Wakes Up
This is the part that actually changed everything.
I am up every morning between 6:00 and 6:30. No exceptions, no negotiating with myself. And before I go into Charlie’s room to get him out of his crib, I am fully ready — outfit, skincare, hair, makeup. Done. Because once he’s awake, I’m not getting that window back. Full disclosure: I don’t go into the office every day. On WFH mornings I skip the makeup, throw my hair in a clip, and finish getting ready after drop-off. Skincare is non-negotiable regardless. The rest is situational.
I also use that time to make his breakfast, start my coffee, and get his backpack squared away. You’ve already seen the bag — but the system inside it is the thing. Every night, I make his lunch, pack it in his lunchbox, and put it in the fridge. So in the morning, all I have to do is grab an ice pack from the freezer, drop it in, fill up his water bottle, zip the bag, and leave it in the same spot by the door.
One thing I didn’t anticipate: you need a backup lunchbox (and another one). Spills happen, things come home wet, and you do not want to be scrambling the night before if it isn’t done being cleaned or is still drying. We got a second one and extra Tupperware and it has already saved us more than once.
The Wake-Up Wild Card
Charlie’s sleep is great but wildly unpredictable. Some mornings he’s up at 6:00. Others it’s closer to 7:30. There were mornings not long ago where he wouldn’t surface until 8:15 — which is lovely, and also completely incompatible with an 8:00am departure.
What’s helped: once he wakes up, we have a sequence and we don’t deviate from it. We go potty. Brush teeth. We get dressed. We go downstairs.
That last part matters more than it sounds. On weekends he comes down in pajamas and does breakfast in his pajamas — I love a slow pajama morning as much as anyone. But on school days, we get dressed first. Full outfit, upstairs, before we ever come down.
The act of leaving the upstairs — his room, his playroom — and coming down in real clothes signals something to him. We are going somewhere. The day has started.
We had to transition back to a full smock bib (another option we love) at breakfast, which took some getting used to again since we’d phased them out, but school clothes need to survive breakfast and that’s just the reality.
And then — this is the part I love — Charlie grabs the bag on his way out and puts it in the stroller himself. He is two. He has a job. He takes it very seriously. It is the cutest thing I’ve ever seen and it also genuinely helps us get out the door.
We also always have some extra breakfast fruit for the walk over to school. Handing him his fruit snack to eat on the way is something he looks forward to. And what he doesn’t finish on the stroll, he gets to finish at school. Honestly, peeking into the classroom and seeing all of the two-year-olds sitting at their little tables finishing their fruit is the most adorable thing ever.
What We Love — and What We're Still Working On
This is the part where I have to stop myself from texting everyone I know every single week.
As mentioned, Charlie is in a Spanish immersion classroom, which means at two he is learning Spanish and English simultaneously — just absorbing both languages at once — and apparently having an absolute ball with it. Every day there’s a new word. Every day I am floored by him.
Every week, a different student gets to bring in flowers from home. Each kid gets their own votive and arranges their own little bouquet — two-year-olds, choosing stems, figuring out what goes where. The finished arrangements get placed around the classroom to decorate. Charlie always feels so proud of his. I think about this more than I should.
Every Friday, the class gets on the rope and walks to the local fruit stand together. They pick out different fruits and buy them from the produce guy. They bring everything back to the classroom, wash it, slice it, and put it in the blender. Charlie comes home on Fridays having had a snack that he had a hand in making from start to finish — from the sidewalk to the smoothie cup. At two. I cannot.
And each student has their own plant. They water it every week. They move it around the classroom to find the light. He is two. He is learning responsibility, independence, and how things grow. This is exactly what we hoped it would be.
That said, we’re still working on a few things. At home, Charlie averages about two hours at nap. At school, he’s getting closer to 60–75 minutes. He’s in a cot instead of his crib. He’s wearing shoes. We had to phase out the sleep sack. There are no blackout curtains. It’s a classroom. We’re three weeks in and nap times are trending longer, which is all I can ask for. We’re getting there.
Pickup
I cannot overstate this: pickup is the highlight of my day.
I have never in my life seen someone belly giggle that hard just at the sight of me. It is the single greatest thing that has ever happened to me on a Tuesday afternoon. Every single time, it reconfirms every decision we made. Ten times over.
Closing Thoughts
There’s something about leaving your kid at school for the first time, in real life, that takes a minute to metabolize. Drop-off is fast — you knock on the door, hand them off and walk out. Then you’re on the sidewalk and it’s quiet and you just stand there for a second.
I know he’s fine. He’s better than fine — he’s thriving, he’s laughing, he’s learning Spanish, he’s belly giggling at pickup. I know all of this. And yet, with another baby coming, I’m aware that this version of the morning — just Charlie and me, walking to school, him with his fruit, me with my iced coffee — has an end date. This specific routine, this specific ratio, is temporary. So I’m trying to be in it. Even when we’re sweaty. Even when we’re almost late. Even when the banana has a brown spot.
I’ve gone ahead and linked all of Charlie’s first month of school outfits on ShopMy.
You can also always find everything I purchased ahead of school starting in my original post and on ShopMy.