5 Remarkable Books to Help You and Your Little Ones Conquer the First Day of School

Are you worried sick about your child’s upcoming first ever day of school? We bring you a selection of books for both child and parent to calm those nerves!

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The clock is ticking, summer is over, and back to school is just around the corner! It’s likely that sentence either fills you with excitement or dread. If you’re a new parent, you’ve probably anticipated this all summer. Wondering how you’ll cope with your little one being so far away for the first time. Did you pick a safe school? Will your child be too nervous to go? If you’re seeking answers to those questions, there’re a multitude of children and parenting books solely dedicated to helping with your child’s possible separation anxiety as well as offering a variety of methods to aid you in making the transition from constantly having your child at home to them being away for hours at a time. So, read on to discover our wonderful selection of books for both parent and child and how to tackle this school year!

The Kissing Hand by Audrey Penn

Two racoons--one small and one big-- stand on the grass in front of a yellow moon. The large racoon is holding the hand of the small racoon. The title sits against the yellow moon. The author's name is at the bottom in white lettering. Everything is set against a blue background with leaves bordering the left and right sides.
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The Kissing Hand by Audrey Penn is a heartwarming one and remains a popular pick amongst kindergarten teachers. The touching picture book narrates the tale of a young raccoon who is nervous about his first day of school. To comfort the young racoon, the mother raccoon shares with him a special family tradition. She gently kisses his paw to help reassure her son, further soothing him by telling him to press that paw to his cheek whenever he misses her. Reading this book to your younger children can help ease that anxiety of going to school so soon and the fear of being alone. Penn helps showcase that even when apart, parent and child can still feel connected, which helps your child feel more confident about this new experience of being away from home.

First Day Jitters by Julie Danneberg

A girl is lying in bed with her blanket up to her nose and a cat sitting on her pillow. They both stare nervously at the calendar that had a big yellow school bus on the picture. On the calendar reads "First Day of School" circled in big red ink.
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A truly classic children’s story by Julie Danneberg that you may have heard of before. Little Sarah Jane Hartwell refuses to get out of bed and go to school. She is petrified at the idea of going to a place all alone and being surrounded by people she doesn’t know and who don’t know her. After a while, her father manages to convince her to head to class anyhow, to her dismay. However, she is quick to be proven wrong and makes friends incredibly quickly. At the end of it all, Sarah learns a valuable lesson —everyone gets a little jittery sometimes. This normalization of nervousness and anxiety can help both the child and parent alike feel a sense of comfort.

The Night Before Kindergarten by Natasha Wing

A girl is laying on her bed getting ready for school in the morning. She is packing her backpack with crayons and notebooks. Her outfit for the day is laid out on the chair next to her, a yellow shirt, blue jeans, and red shoes. All while her dog looks up at her with his paws on the bed.
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Part of author Natasha Wing’s The Night Before series, this touching book is aimed at exciting children about their first day of school by familiarizing them with what to expect. It has an engaging rhyme scheme that captures the children’s attention. The ending of it may also help soothe the adult’s worries by demonstrating how kindergarten can be a fun and safe place for your children. Furthermore, this picture book helps serve as a supporting tool for the whole family as they navigate the important milestone together.

The Starting School Book: How to Choose, Prepare for and Settle Your Child at School by Sarah Ockwell-Smith

A young boy is wearing an orange backpack holding his parent's hand while looking up at them. In front of a blue background.
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The Starting School Book is not a children’s book this time, but rather a self-help book geared toward newer parents. This parenting manual serves as an accommodating guide for those whose children are about to start school. Author Sarah Ockwell-Smith is well-versed in the world of parenting books, and so her advice can help assist you with any worries you may have about this upcoming school year, including how to help smooth the transition from having kids at home each day to sharing their time at school without any bumps.

Don’t Forget Your Sunglasses: A Parent’s Survival Guide to Kindergarten by Dr Kathleen Molnar Benyo

A boy with a blue backpack and a blue checkered shirt is shown hugging the waist of his teacher.
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Dr. Benyo’s guide is much broader in comparison, as her book is much more practical. With clear and concise suggestions, Dr. Benyo focuses less on reassurance and more on the specific concerns one might have. Her experience as a teacher at an elementary school, a former principal, and a college professor helps highlight her credibility in this subject. While easing anxiety is very important, perhaps it might also ease the mind by focusing on other concrete specifics, as well, such as ideas on how to talk to a teacher, details on how the day will plan out, and other helpful tips.

So, whether you’re a kid who’s entering their first day or a jittery parent not ready to see your little one go off for the first time, don’t panic. School isn’t here just yet; there’s still plenty of time left to prepare for this milestone. But when that time comes, it can be helpful to remember that the first day of school is a thrilling turning point for a child — and parent — after all!


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Find these books and more on our Back-to-School Recommendations for All Ages bookshelf on Bookshop.org.

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