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The Preschool Transition I Wasn’t Expecting
May 15, 2026 | Motherhood
And then there's me.
I adore the fact that I get to walk my daughter to school. It’s something I always dreamed of doing as a kid. There is something so simple and special about having our morning chats, walking together, and starting our day this way. It also happens to double as a workout because our walk is very hilly, so I guess I’ll take that as another win.
But perhaps the biggest surprise has been what this new routine has done for me. Having a straightforward childcare schedule allows me to shut that side of my brain off. Same time, same place, every day. What worked previously, worked for that season and what is working now is for now.
When I’m alone, I can be laser-focused on work. I’ve been able to accomplish so much in a day because I know when I’m working and when I’m parenting. There’s less mental juggling and more clarity.
I know this season won’t be perfect. I know illness will strike. There will probably be mornings when she refuses to get dressed. There will be hard drop-offs, hard days, and moments when preschool feels like a lot. But for now, I’m letting myself enjoy this.
Two weeks in, my daughter is walking into school with confidence.
She’s making friends.
She’s showing empathy.
She’s getting covered in paint and food and whatever else preschool throws her way.
And I’m learning that sometimes the transition we spend so much time worrying about turns out to be much gentler than we imagined.
Maybe preschool isn’t just a new chapter for her. Maybe it’s one for me, too.
And right now, these days are better than I ever could have asked for.
But perhaps the biggest surprise has been what this new routine has done for me. Having a straightforward childcare schedule allows me to shut that side of my brain off. Same time, same place, every day. What worked previously, worked for that season and what is working now is for now.
When I’m alone, I can be laser-focused on work. I’ve been able to accomplish so much in a day because I know when I’m working and when I’m parenting. There’s less mental juggling and more clarity.
I know this season won’t be perfect. I know illness will strike. There will probably be mornings when she refuses to get dressed. There will be hard drop-offs, hard days, and moments when preschool feels like a lot. But for now, I’m letting myself enjoy this.
Two weeks in, my daughter is walking into school with confidence.
She’s making friends.
She’s showing empathy.
She’s getting covered in paint and food and whatever else preschool throws her way.
And I’m learning that sometimes the transition we spend so much time worrying about turns out to be much gentler than we imagined.
Maybe preschool isn’t just a new chapter for her. Maybe it’s one for me, too.
And right now, these days are better than I ever could have asked for.
The dirty clothes are a gift.
There is another thing I’ve noticed in these first two weeks that I didn’t expect to appreciate so much: the dirty clothes. From the very first day, Rafaela has come home with at least one or two dirty outfits. We are constantly replenishing her cubby with clean clothes too.
At first, I was mildly frustrated. I thought about the laundry. I thought about stains. I wondered how many extra shirts and shorts I was going to have to buy. And then I realized: what a gift it is to have a child come home with dirty clothes.
Dirty clothes mean she played. They mean she laughed, painted, explored, ate something delicious, probably spilled something, and got completely immersed in her day. They are evidence that she was busy being a kid.
So yes, I bought a few more shirts and pairs of shorts. And yes, I’m still figuring out the stain situation. I’d much rather have a child come home covered in the evidence of a good day than come home perfectly clean because she was too nervous to participate or there was nothing actually fun going on.
At first, I was mildly frustrated. I thought about the laundry. I thought about stains. I wondered how many extra shirts and shorts I was going to have to buy. And then I realized: what a gift it is to have a child come home with dirty clothes.
Dirty clothes mean she played. They mean she laughed, painted, explored, ate something delicious, probably spilled something, and got completely immersed in her day. They are evidence that she was busy being a kid.
So yes, I bought a few more shirts and pairs of shorts. And yes, I’m still figuring out the stain situation. I’d much rather have a child come home covered in the evidence of a good day than come home perfectly clean because she was too nervous to participate or there was nothing actually fun going on.
Maybe we were preparing for this all along.
Looking back, I think a few things helped make this transition smoother.
First, Rafaela was already somewhat familiar with being “dropped off” for extended periods of time outside of our home. She had been part of a nanny share, where she would spend time away from us and go to the playground and participate in activities with other caregivers and children.
That initial transition was difficult. We sang the Daniel Tiger song “Grown Ups Come Back” a lot, but now I can see that it probably paved the way for this one. She had already experienced the idea that Mom and Dad leave, and that Mom and Dad come back.
The second thing we did was something I’ve come to believe is one of the most underrated toddler-parenting skills: marketing.
Or, as I like to call it, rebranding.
We really hyped up preschool.
“Your cousin goes to school every day! He packs a lunch and plays on the playground. You should ask him about school!”
“Let’s go pick out a backpack so you can put all your snacks in it.”
“At school, there’s a beautiful garden where you’ll get to plant vegetables!”
We talked about school with genuine excitement. And I think that matters. Kids pick up on our energy more than we sometimes realize. If we communicate that something is exciting, special, and worth looking forward to, they have an opportunity to mirror those feelings.
The third thing that helped was attending all of the activities leading up to the first day. We went to the open house and a playground meet-up, which gave Rafaela a chance to see the school environment, meet some of her future classmates, and become familiar with her teachers. It also gave her something to look forward to.
She got to explore the classroom, see the toys, and start building a mental picture of what school would actually be like before we asked her to walk in on her own.
By the time the first day arrived, preschool wasn't completely new anymore.
First, Rafaela was already somewhat familiar with being “dropped off” for extended periods of time outside of our home. She had been part of a nanny share, where she would spend time away from us and go to the playground and participate in activities with other caregivers and children.
That initial transition was difficult. We sang the Daniel Tiger song “Grown Ups Come Back” a lot, but now I can see that it probably paved the way for this one. She had already experienced the idea that Mom and Dad leave, and that Mom and Dad come back.
The second thing we did was something I’ve come to believe is one of the most underrated toddler-parenting skills: marketing.
Or, as I like to call it, rebranding.
We really hyped up preschool.
“Your cousin goes to school every day! He packs a lunch and plays on the playground. You should ask him about school!”
“Let’s go pick out a backpack so you can put all your snacks in it.”
“At school, there’s a beautiful garden where you’ll get to plant vegetables!”
We talked about school with genuine excitement. And I think that matters. Kids pick up on our energy more than we sometimes realize. If we communicate that something is exciting, special, and worth looking forward to, they have an opportunity to mirror those feelings.
The third thing that helped was attending all of the activities leading up to the first day. We went to the open house and a playground meet-up, which gave Rafaela a chance to see the school environment, meet some of her future classmates, and become familiar with her teachers. It also gave her something to look forward to.
She got to explore the classroom, see the toys, and start building a mental picture of what school would actually be like before we asked her to walk in on her own.
By the time the first day arrived, preschool wasn't completely new anymore.
We are a couple weeks into preschool, and it’s going better than I ever anticipated.
Honestly, I wasn’t confident this would be the feeling. I expected tears, uncertainty, maybe a little heartbreak at drop-off (there was on my end haha). I was worried that she would feel lonely without her friends or feel scared to be in a completely new environment.
Instead, I’ve been met with something I didn’t quite expect: confidence, curiosity, and my daughter who seems genuinely excited to be there.
And, if I’m being honest, this has been a huge sigh of relief.
At pick-up yesterday, I had a chance to chat with another parent from my daughter’s class. He told me that Rafaela had helped welcome their daughter into the classroom that morning. His daughter was feeling sad at drop-off, and Rafaela invited her to sit down and read a book with her. My heart sang as he shared this.
Watching your child show empathy and inclusivity is such a beautiful thing. Maybe that is simply part of her nature. Maybe it’s a little bit of parenting, too. I don’t know. All I can say is: wow. It made me incredibly proud.
And seeing her walk into the classroom with confidence and curiosity has been a huge relief. I had prepared myself for tears, and instead, I watched her walk through the doors ready to see what the day has in store.
I think that has made the transition easier on me, too.
Honestly, I wasn’t confident this would be the feeling. I expected tears, uncertainty, maybe a little heartbreak at drop-off (there was on my end haha). I was worried that she would feel lonely without her friends or feel scared to be in a completely new environment.
Instead, I’ve been met with something I didn’t quite expect: confidence, curiosity, and my daughter who seems genuinely excited to be there.
And, if I’m being honest, this has been a huge sigh of relief.
At pick-up yesterday, I had a chance to chat with another parent from my daughter’s class. He told me that Rafaela had helped welcome their daughter into the classroom that morning. His daughter was feeling sad at drop-off, and Rafaela invited her to sit down and read a book with her. My heart sang as he shared this.
Watching your child show empathy and inclusivity is such a beautiful thing. Maybe that is simply part of her nature. Maybe it’s a little bit of parenting, too. I don’t know. All I can say is: wow. It made me incredibly proud.
And seeing her walk into the classroom with confidence and curiosity has been a huge relief. I had prepared myself for tears, and instead, I watched her walk through the doors ready to see what the day has in store.
I think that has made the transition easier on me, too.
