Books about going to school recommended by PSP members:
Pete and Polo's Big School Adventure by Adrian Reynolds
I Love You All Day Long by Francesca Rusackas
Oh My Baby, Little One by Kathi Appel
My First Day at Preschool by Edwina Riddell (only used copies available)
Making Friends by Fred Rogers
You Go Away by Dorothy Corey
Curious George's First Day Of School by Margaret and H.A. Rey
Some of these titles are available as YouTube Videos. Sesame Street also has some great videos. Search "school," "kindergarten," and "first day of school."
Here are some tips to help with the adjustment:
Play it up in the weeks beforehand. Talk about new friends, new toys, new activities, a special cubby just for them, special kid-sized chairs and tables. Listen to them and reassure them that it's going to be great If you've been preparing them for school so far, you've calmed their nerves about things they could be nervous about—yes, they will be able to eat; yes, there is a bathroom; yes, there is quiet time (but they don't have to nap); yes, they will get picked up—then this is a new adventure that they are ready for! Walk by the school and play area (if possible) so they can take a look. If the school has a way to meet the teacher beforehand, that can help, as can just seeing a photo of them. If your child need supplies like a backpack or lunch box, let them pick out what they want to give them a sense of agency.
Start a bedtime routine early. Kids thrive with repetition at bedtime, so if you can, start a few weeks beforehand and implement a post-summer routine to take you into fall.
Meet up with new school buddies. Having a playdate with other kids in the class will help with the transition. If you can meet up and go together with a school friend on the first day, that may also help. If you're a PSP member, you can ask your baby group to find other kids going to your school.
Play pretend school. Make the day fun and include all of the elements that school will have (play time, circle time, lunch time, recess, etc.).
Create a good-bye routine. Invent a new secret handshake, figure out funny faces you can make as you leave, or create any other type of ritual. Keeping things consistent can help your child more quickly acclimate to the new surroundings. You might want to rehearse the routine the night before.
The night before. Before bed on the night before, talk through the morning routine ("We'll get up, have breakfast, get dressed, get our gear together, and walk to school") so expectations are set. (You might also want to put together a "Morning Routine" chart with times that things should be happening.) Set the tone of what good-bye will be like. Make lunch the night before if you can—and let kids help. Let them pick out the clothes they want to wear. Start the bedtime routine early so that you can get the lights out early.
Set out what everyone will wear the night before. To keep the nerves from devolving into an "I don't know what to wear" battle, have everyone pick out clothes the night before.
First day of school. In the morning, give yourself an extra 15 minutes and leave early. Try not to rush around—that will just make everyone more tense. If you can, give kids a sense of control by letting them help fix their lunch. Show up to school a bit early if possible so it's less overwhelming with all the other kids your child may not know. If your child has a "lovey" that makes them more comfortable, let them bring it (unless it's not allowed by the school).
Remember the first day of school photo! Consider doing something that can become a tradition, like holding up a sign with their grade. Here are some great ideas!
During drop-off, stay positive and upbeat. Be prepared for them to be teary and upset. Don't stick around too long—that just makes it harder for both of you. When you leave, reinforce that they will have fun, that they will make friends, and that school is good for the whole family. Don't ask if it's okay to leave; just be firm and say it's time for you to go. (And don't try to skip out without them knowing—tell them you're going). Also, tell your child when you (or some other caregiver) will return to pick them up.
Give them a "one friend" goal. Ask them to make a new friend each day and to introduce you to that new friend. It can give them something to do and divert them from their nerves.
Back up and let them find their own space. Don't interact unless you absolutely have to. Let them get comfortable without you.
Adjust quickly with a photo collection idea. One thing that helped my new preschoolers was to take photos of the students and teacher on the first day of school, load up the photos, and have her tell me the names of the students as well as what her new friends were like. (Many times, the class will wear name tags, which helps you learn the names). Somehow seeing the kids on the computer at home made it more a part of her life instead of "that place" she has to go. She also got to know the names of the other kids quickly, which helped her feel more comfortable with her classmates. (I also put them up on a photo sharing site and sent them out to all the other parents to help their kids as well. This requires a bit more planning, like collecting other parents' emails, and more energy, but it's well worth it if you have the bandwidth).
What about parents who might have a hard time adjusting?
Keep your own emotions in check. You may be feeling torn and anxious yourself, but realize that the teachers have done this all before and know how to redirect kids' energies to something more fun. Your child will pick up on your nerves and your mixed emotions. Deep down, you know that this is good for them; let that confidence show. It will be okay. The school knows your number if something happens or they need you.
Do something fun that makes you feel good. The first day of school may be more difficult for you than your child, with mixed emotions of relief, joy, and terror. Remind yourself that you can't be with them forever—school is a great way to help them grow up without you, as hard as that is right now. Get teary after you leave your child if you feel the need (I still did when my oldest was going into fifth), and spend the time doing something for you; my guess is that you could use a little more TLC.
Final reminder: Teachers are experts at managing transitions. Rely on them to know how to interact with different types of kids. Trust them to be your guide; they will know how to help your kids.
Good luck on the first day of school!
Samantha on her first day of preschool way back when!
Further reading from around the web: