Planning for the School Year


I left teaching to raise my children at the end of the 2014 school year. Even after four years, it still feels weird heading into September with no lessons to plan, supplies to purchase or classrooms to set up.


Instead, I’m looking ahead to the new school year as a parent. This year, both of my daughters will be in nursery school. My four-year-old will be in pre-K for five mornings a week and my two-year-old will be attending the two-year-old class for three mornings.


Despite having six weeks to go before the year begins, we’re already received registration information for the fall, which means the first day will be here before I know it.


My older daughter has two years of school under her belt so she knows what to expect. She’s excited to see her teachers and friends regularly again. We’ve been talking up the new year regularly, hoping to interest my younger daughter in what’s to come and prepare her for the new experience.


She has accompanied me for preschool drop off and pick up the last two years. This past year, she often walked right into her big sister’s classroom and tried to play with the toys or do an art project, which ended with me carrying her out while she loudly protested.


I’m hoping school will be an easy transition, but I never quite know how she’ll react to anything. Talking regularly about school will hopefully serve to get her excited. I’ve also taken some simple steps to help ease her in.


Let Your Child Pick out Supplies


Of course, preschool doesn’t ask for much in terms of supplies, but I need to buy a backpack and school labels. My youngest sat down with me and picked out the backpack and label design she wants. She’s very excited to have a unicorn backpack and labels with her name and a picture of a cat on them.


Choose a First Day of School Outfit


My youngest is just getting to the age where she has definite opinions about what she wants to wear. Choosing a special first day of school outfit together is a fun ritual that my older daughter also really enjoys. Even better if the outfit is a new one that you took them to buy especially for the first day.


Meet the Teacher Together


My youngest starts the day after my oldest, so she’ll have a day to remember the routine of drop off and pick up. After we drop my older daughter off, I plan to walk my younger daughter to her classroom to look inside and say hi to her teacher.


We’ll visit her cubby and talk about what the next day will be like. I’ll take a couple minutes to point out the indoor play space, the bathrooms and the playground and remind her how much fun she’ll have the next day.


Play Pretend School


My daughters both love to engage in creative play. In the remaining weeks of the summer, I’m going to enlist my older daughter to play school with my younger daughter. I’ll encourage her to teach her little sister the songs and games that she remembers, as well as rituals like circle time and snack.


Helpful Books


Audrey Penn’s “The Kissing Hand for Chester Raccoon” is one of the many wonderful books about going to school for toddlers. My girls are especially fond of this one and I plan to make sure we read it a lot over the coming weeks. Another option is to watch an episode of a favorite show that focuses on the first day of school. There’s a wonderful Daniel Tiger episode that I plan to show this summer.


First Day Fun


The first day comes with the obligatory first day of school picture. I have a cute little chalkboard that I fill out with the girls. It’s fun to ask them questions like “what do they want to be when they grow up” and “what are they most excited for about school.”


As a parent, there’s a lot to remember for the start of the school year. This is what I aim to do in August:


Label Everything!


My daughters are only in school for the mornings, so I don’t have a ton of items to send in with them, but I make sure their change of clothes, backpack and outerwear are clearly labeled. I love Mabel’s Labels for cute and personalized clothing stickers.


Pack Appropriate Changes of Clothes


A change of clothes is required for preschool. I pack a gallon Ziploc bag or cloth diaper wet bag (clearly labeled) with seasonally appropriate clothes. I think of layers: a short sleeved shirt, a sweater or sweatshirt and long leggings so I don’t have to change the clothes season to season. Socks, underwear and a pair of shoes (so important for early potty training!) also go in the bag. Every item is labeled.


Get into a School Year Routine Over the Summer


This is hard. Over the summer, we’ve become so used to later bedtimes and lazy mornings, but to prevent an insane rush in the mornings, the kids will have to get up earlier for school days. I tend to stick to a 7:30 wake up even over the summer, but I’ll probably start aiming for a 7 or 7:15 wake up two weeks before school starts.


Right after Labor Day Weekend, we’ll start aiming for early bedtimes and an earlier wake up. Don’t try to do this the night before school starts. Children (and parents!) need time to adjust.


Mentally Prepare for Drop Off


Leaving your child at school can be just as emotional or scary for parents as it is for children. One piece of advice that I received from multiple preschool teachers is “do not linger!” Walk your child in, be cheerful, give them a big hug and a kiss and leave.


If you stick around, you’ll only draw out your child’s sadness (and your own!). Trust that the teachers are professionals in early childhood and will help calm and distract your child. When I dropped my older daughter off for the first time, I managed to get out the door quickly, and broke down crying in the parking lot. The director of the school invited any parents to call throughout the morning and check in, or cry in her office, or wait on the stairs to collect themselves. I left because my younger daughter needed a nap, but I called in after about an hour to check in. The only two times she cried during drop off was when I stuck around, chatting with another parent. I learned my lesson and made sure I quickly exited the school. By her second year, this was no longer an issue, but I have to make sure I take my own advice in September when it comes to dropping my baby off.


Develop a Special Goodbye


If drop off is still difficult after the first week or so (our director assured us that it’s totally normal for a preschooler to break down during drop off at least once in the first two weeks), come up with a special goodbye: a handshake, secret phrase or special song—anything to signal that it’s time for the parent or caregiver to leave. Kids thrive on routine, so hopefully this will be helpful for everyone.


Talk About School


On the car ride home, or over lunch, ask about their day. My youngest may not be able to tell me much, but I’ll ask what she had for a snack or what she did on the playground. If she brings home any art projects, I’ll ask her to tell me about them.


Keeping her excited about the day and looking forward to the next day of school is so important!


Getting ready for school is an important end of summer ritual. Older children may drag their feet, dreading the return to the school year routine, while younger children may have no idea what to expect and therefore be terrified.


As parents, it’s our job to keep our children calm and help them feel safe. Be cheerful, reminisce about your favorite school experiences and make sure they know how excited you are for all the wonderful new experience they will have.


As hard as it is to let go of our children, think about what school means for you. Time to run childfree errands. Time to try a new class at the gym or get your nails done. Time to start that home improvement project you’ve been meaning to tackle. This is your time as much as theirs, so enjoy the rest of the summer and happy back to school, everyone!



Dorothy Sasso is a Lifestyle Writer for She’s It, LLC. She has written for “Soap Opera Digest”,, and the Wilkes-Barre Times Leader. Her work focuses on infertility, pregnancy and parenting, and also includes book reviews, features, interviews and event previews. After leaving a teaching career to raise her two daughters, she has loved returning to her roots as a writer. Currently, she is working on a novel and launching an online support community for people struggling to have a child. Follow her progress and join the community at, on Twitter (@maybebabyclub, @dorothysasso), on Instagram (maybebabyclub) and on Facebook. She lives outside of Philadelphia with her husband, daughters and two cats.