Tips for Easing Your Little One Into Preschool
From a mama who just did it!
Today is a bit different because we are talking about sending Olive to pre-school. I have gotten so many questions in my DM’s about how Olive is transitioning, how I did it and what tips I have. Thats why I am writing this, in hopes that it can reach all of the parents that ARE or WILL send their toddlers to pre-school or daycare soon.
Disclaimer, I followed my intuition and created a gentle plan that worked for us. In this post, I’m sharing everything we did to prepare her for the transition. Here’s what I will cover!
How we chose the right school
Ways we introduced the space + her teacher
The song that made drop-offs easier
Our go-to books and role play ideas
Gentle ways to build confidence and social skills
Our exact first-week schedule
A small daily ritual that’s become her favorite part of pickup
If you’re starting daycare, preschool, or just thinking ahead, I really hope this gives you some peace and ideas to carry with you! Share this with a mom friend who is taking the big leap!
How I created a plan
I usually don’t read a million parenting blogs or research the “right” way to do things.
I lead with my intuition and heart, especially for big transitions like starting school.
So if you’re reading this and you're in the same season of transition, I just want to start by saying: trust yourself!! You know your little one better than anyone (and I constantly have to remind myself of that too with all of the advice being thrown around).
I hope my plan it gives you a few ideas or even just the reassurance that you’re doing great!
Tip #1: Choose the Right Preschool FOR YOU
We toured six different preschools in our area.In the end, we picked based on one thing: energy and safety. Sure, we also considered price, class size, playgrounds, food, and safety. But I just knew when I walked in which space felt safe, warm, and loving. That’s the one we picked. I urge you to look into the values that mean the most to you. Do you want a small class size, outdoor play, do you want them to prepare food for the kiddos, do you want them to learn anything specific?
Tip #2: Take your time
Once we chose the school, we gave ourselves a three-month runway before she officially started. Not necessarily planned, but I knew that the schools filled up so quickly! But that extra time allowed us to introduce the idea of school slowly and gently, without feeling rushed.
Tip #3: Get Familiar with the Space
Once we decided on the school, I spoke with the director to see if they would let us visit the playground during school hours. I’d take her there just to play while I stayed nearby, and she got used to the physical space. She even saw some of the kids from a distance. It helped her feel safe and familiar with her new environment before her first day. GAME CHANGER.
Tip #4: Introduce the Teacher Early
We received a little bio and photo of her teacher, and we started talking about her often at home. We’d say things like, “Miss Gabby is going to help you paint!” or “She’ll sit with you for snack time.” It made her feel like part of our circle, before they even met.
Tip #5: Reading and Pretend Play
We got a few preschool-themed books and used them to role-play. I’d point to the teacher in the book and say, “Look! That’s Miss Gabby!” Or “That’s you, sitting with your friends!” It helped her visualize what school was going to feel like.
Tip #6: Songs and Shows!
Save this song: Daniel Tiger’s “Grown-Ups Come Back”
This song was a lifesaver. We played it often, and I’d remind her: “Mommy and Daddy always come back.” It gave her words for something she was feeling but couldn’t fully express.
YouTube: Miss Rachel Getting Ready for Preschool
We also played a few of Miss Rachel’s school prep videos on YouTube. They helped explain the school experience in a really simple, comforting way that made sense to her.
Tip #7: Sign Up For Group Activities Beforehand
To help her get comfortable around other kids, we did a mix of:
Library story-times and classes
Music and movement classes
Playdates with friends
Unstructured park time with other kids where I let her explore without hovering
It helped her build confidence in playing with others and understanding the rhythm of group activities.
Tip #8: Teach Boundaries
Because I knew I wouldn’t be there to step in every time, I gave her a phrase to use when needed: “Stop. Don’t do that.”
We practiced saying it with confidence. I just wanted her to have the tools to stand up for herself if she ever felt uncomfortable 🥹
Tip #9: Eased Into the Schedule
She started school at 2 years and 1 month. It was a summer program, Monday through Friday, 9 AM to 12 PM. But for the first three weeks, we only sent her three days a week (Monday, Wednesday, Friday). I didn’t want her to jump into a five-day schedule cold turkey. That gradual start helped her adjust without feeling overwhelmed. I felt like at that age, it’s not so “serious” and taking a few days off was such a great way to ease into it!
Tip #10: Create Special Traditions
Once she started, I did small things like go to the grocery store and let her pick out a snack that she was excited about for snack time. That snack is something we only get to eat at “school.” So we went with freeze dried strawberries.
Every single day when I pick her up, I bring the same exact snack, raisins and walnuts. It’s her favorite. Now she knows that when Mommy shows up, she gets her special snack on the way home. That consistency gives her something to look forward to and creates a little post-school routine she loves.
Now that she’s in it, I can confidently say: it’s been amazing.
She’s doing things she would never do at home; sensory bins, painting, dancing with other kids, and learning from teachers. It’s given her so much joy and independence.
If you're prepping to send your little one to school or daycare, I just want to say this:
You’re doing a beautiful job. You don’t need to do everything perfectly or follow someone else’s timeline. Just listen to your gut, follow your child’s cues, and know that your love will carry you both through.
Share this post!
If you’ve already gone through this transition, I’d love to hear how you prepared your littles for school. Drop your tips in the comments so we can all learn from each other. And if you have any questions for me, I’d be happy to answer them.
You have learned so much. The best way to learn is through experience. I am so proud of you mama!