As the school year approaches, you are probably wondering how to prepare your child for preschool.
While all children respond to situations differently, it’s very likely that a transition this big will cause some anxiety for your child.
This doesn’t mean that they aren’t ready for preschool, simply that you need to be proactive in preparing them both emotionally and with the skills they need to thrive in the preschool setting.
We went through this experience with our son, Theo, who is a very sensitive child. I’ve narrowed down the things that worked (and didn’t work!) and made a list for you of 8 tips to prepare your child for preschool.

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Before Preschool Starts
1. Talk to Your Child About Preschool
Make sure to tell your child about all of the fun things that preschool has to offer. If they love art, let them know they can color and paint at school!
If trucks are their favorite toy to play with, inform them that there are probably a lot of vehicles to play with at preschool.
Don’t just talk about preschool, but read books and watch television shows about the first day of school.
We are big Daniel Tiger fans in our house, but there are books and shows with almost every character.
I’ve suggested many below, but you can also talk to your librarian to see what they recommend!
Books
- Maisy Goes to Preschool: A Maisy First Experiences Book
- Daniel Goes to School (Daniel Tiger’s Neighborhood)
- The Night Before Preschool
- Curious George’s First Day of School
- Amelia Bedelia’s First Day of School
- Time for School, Mouse! (If You Give a Mouse a Cookie)
- Spot Goes to School
- Rosie Goes to Preschool
T.V. Shows
- Dora the Explorer First Day of School
- Sesame Street: Abby Cadabby’s First Day of School
- Daniel Tiger: Daniel Visits School (youtube)
- Daniel Tiger: Daniel Goes to School (youtube)
2. Don’t Talk to Your Child About Preschool Too Early
Young children have NO CONCEPT of time.
If you tell them in advance, they are going to wonder when it’s going to happen, and it’s probably going to cause them a lot of anxiety.
We learned this the hard way.
Theo went to a special early childhood preschool program at 2.5, and when he turned 3, he had to switch schools because the cutoff at his current school was 3.
Since we toured his new school and met the teacher, I told him what was going to happen.
That was a BIG mistake.
Everyone noticed that for the next few weeks he was very anxious, so we dropped it completely.
I didn’t even tell him on his last day that he wouldn’t be going back.
He started his new school on a Monday, so on Sunday night, I told him he would be starting his new school the next morning.
How do you balance talking to your child about preschool, without telling them too early? I would suggest talking to them about it with a vague timeline.
“When you’re bigger, you will go to school just like Daniel Tiger and play with all of the toys there!”
This sounds less threatening than just saying “you’re starting school!”

Read –> The Benefits of Separating Twins for Preschool
3. Teach Your Preschooler to Speak Up For Themselves Appropriately
Theo, being a sensitive child, would just let another child snatch a toy for him or boss him around, without saying anything.
We talked to him about speaking up and saying nicely “no thank you, I was playing with that, you can have it when I’m done.”
Other children may react differently; some may instinctually tattle, others respond by hitting or snatching back.
We also told him very clearly that if another child is to hurt him or someone else that he is to tell his teacher.
Read –> The Benefits of Putting Twins in the Same Class in Preschool
4. Work on Self-Help Skills with Your Preschooler
Some preschools are very hands on and it is a good idea to check with the teacher to verify which skills are important for your child to know. Here are the skills that we worked on with Theo before he started preschool.
- Pulling pants and underwear up after using the potty (tip: if they can’t yet fasten buttons, send them in elastic wasted pants or dresses)
- Washing hands correctly
- Can follow simple commands such as “clean up,” “stand in a line” and “sit in a circle” (this is a work in progress, right??)
- Putting caps on and off of markers
5. Transition Your Preschooler’s Schedule
If your child has been sleeping in late, slowly transition them a few days prior. Theo sleeps until 8:00 in the summer, but has to wake up at 7:00 to get ready for school. His first day is on a Wednesday, so I will get him up at 7:30 on Monday and 7:15 on Tuesday. If he didn’t adapt well to waking up early, I would spend at least a week preparing him, but I know my child and know that this will work for us
Other Helpful Posts
- 5 Ways to Teach Children Kindness
- Top Board Games for Preschoolers
- How to Handle Your Three-Year-Old (living with a mini tyrant)
First Few Days of Preschool
6. Have a Special First Day of Preschool
For us, I made peach pancakes for breakfast. I made the batter the night before, but it was still a LOT of work. This year, I might make muffins or something else that doesn’t need to actually be cooked the morning of.
Some other ideas to celebrate the first day of preschool:
- Special breakfast (just make sure you actually have time to make and eat it!!)
- Pizza night, or whatever your child’s favorite food is for dinner
- Celebrate with a special snack after school, or going out for ice cream after dinner
- Work on an art project together, such as have them draw a picture of what their first day was like
7. Make Preschool Drop off Brief
Drop off can be really hard. We all went together for Theo’s first day, and to our surprise, he ran in and started playing right away. Great, right?? Wrong. The next few weeks he wasn’t quite as distracted by all of the toys and books and he cried a lot. Since our twins were only 6 months at the time, I stayed home with them, while my husband dropped Theo off at school on his way to work.
My husband would sit with Theo, read a book to him, and try to calm him down before he left. When he told me he was doing this, I told him to stop immediately.
The best thing a parent can do during drop off is to make it as quick as possible. Keep your voice happy and cheerful. You can acknowledge the crying “I know you’re sad that I’m leaving, but remember, I will be back to pick you up after snack. Have so much fun today!” but don’t go overboard with consoling them. When you console them, it typically makes them more upset.
As soon as my husband made the drop offs shorter, his teachers informed us that the crying stopped almost immediately. A prolonged drop off = prolonged crying.
If your child is very schedule oriented, make them a little picture schedule. Theo’s teacher made one for him, and he would cry when my husband left, then flip through his schedule book and recite to himself “first play, then motor room, then circle time, then snack, then mommy comes.” By the time he was done looking through his book he was reassured that I’d come to get him, excited about the day, and the tears stopped immediately.
After writing this post, I sent it to a friend who is a preschool teacher and asked for his opinion. Here is what he said:
“Really you need to rip it like a Bandaid. Push the kid in a run before they realize you’re gone. Sometimes we would have parents who stuck around BECAUSE their child wasn’t upset that they were leaving so they’d stick around until they got the kid crying. “I’m leaving. Are you sad I’ll be at work all day?” Its best to realize and accept it’s harder for the parent than the kid.The teachers and staff will hate you if you’re the parent who can’t leave. They’ve got this. It’s what they do. Push. And run.”
8. Send a Comfort Item to Preschool
Theo would bring 1 small toy from home to play with on the ride to school. We allowed him to take it into school, but only keep it in his backpack. Personally, we steered away from letting him bring a lovey because I just imagined the disaster if he lost it, but that was our personal preference.
Remember, all children are different. Modify these tips however you feel they will benefit your family the best.
Don’t forget to follow me over on Instagram to keep up with our family!


April Kitchens
Thursday 17th of August 2017
These are great tips. The tip about speaking up for yourself stuck out to me. Being around so many children can be intimidating and overwhelming.
Caitlin @Rogers Party of 5
Thursday 17th of August 2017
Thanks, April! It can be intimidating, especially for children who are more sensitive.
Maranda Laverdure
Wednesday 16th of August 2017
Great post. These are really great tips on getting your little one ready. Preschool is a magical time for them, but kind of intimidating for parents.
Caitlin @Rogers Party of 5
Thursday 17th of August 2017
Agreed, I think it's much harder for the parents than for the kids!
Jamie
Wednesday 16th of August 2017
These are fantastic tips! It's such a scary thing to send our kiddos away for the first time but these definitely seem like they'll help get us and the littles on track to prepare for their next big step in life!!!
Caitlin @Rogers Party of 5
Thursday 17th of August 2017
Thanks, Jamie! It's so scary lol, but necessary!
Firenze McCowald
Wednesday 16th of August 2017
These are all really great tips! We did NOT have any problems transitioning to preschool, but I suspect that some of this = my husband is a teacher, and I used to teach. So our kids think going to "school" is fun, and couldn't wait to start. Another great book (and one we used) is Llama Llama Misses Mama by Anna Dewdney - def check it out!
Caitlin @Rogers Party of 5
Thursday 17th of August 2017
Oh, thanks for the book suggestion! I'll add it to the list!!