Surviving the First Days of School: Preschool Edition

How is it possible that the first days of school are upon us again?! I can hardly believe that barely over a year ago I was taking my son Noah to preschool for the first time. And in less than a month, our family will be gearing up for a new school year for both boys. Seeing all of the photos of everyone’s kiddos who have started back to school already has had me reflecting on how those early days went went for us. Surviving the first days of school last year proved to be emotionally challenging. I am very thankful that this year I have some tricks up my sleeve to help the transition go more smoothly for all of us.

Our preschool is a half day program that our boys will attend a couple of days a week. Last year when we decided to enroll Noah in school, our main goal was to provide more opportunities for socialization for him. He has always been a very outgoing child and we wanted to give him consistent exposure to other children his own age as well as to other adult role models. We were incredibly blessed to have him in a class with amazing teachers and overseen by a wonderful program director. All of whom were dedicated, attentive, and genuinely passionate about their work. We saw Noah thrive as the year progressed and his experience was very positive overall. This year we look forward to another wonderful opportunity from which we hope both boys will benefit.

I want to share some of our initial experience and offer suggestions of the things we found to be the most helpful to us in this process. My hope is that doing so may help ease this transition for your family or at least offer a hand of solidarity to those of you who may be struggling or anxious with similar situations.

First Days of School: Preschool Edition - NP's 1st day

The Best Advice I Received

Try not to linger at drop off. Even if you feel anxious.
Especially if you feel anxious.

I can’t remember exactly who gave me this advice. I’m going to credit our preschool director who is a very kind and empathetic person because I feel like this is something she would have gently told me. As a first time preschool parent, my initial interpretation of this was pretty dramatic. The thought of “not lingering” felt more like a suggestion that I shove my kid into a completely new scenario and then abruptly flee the scene of drop off on the first day. And that made my stomach churn with worry.

How would I know that he is ok? Won’t he be terrified if I just LEAVE him there? Shouldn’t I stick around and help him warm up to the newness of it all? If he cries for me, won’t I be scarring him for life if I abandon him like that? Will he ever trust me again? Okay, okay – as you can see – I was feeling a little over the top! But this was MY BABY we were talking about.

This advice is actually very sound.

Noah has always been very “in tune” with my energy. I credit him being a very perceptive kid but also I believe children are incredibly intuitive by nature. Your child looks to you to set the tone. Having a plan that exudes your confidence in any new situation is key. In this instance that may look like: giving a hug and kiss, a cheerful bye-bye with a smile, and saying confidently “I will be back later to get you” as you pass them off to a teacher.

The underlying message you are sending is this: “I trust these people to care for you. I know you will be safe here.”

If I’m being totally honest, I think the very best advice for anything in parenting is: “YOU DO YOU.” Because ultimately that is what is truly best for each of our families. You know your kid. And I believe that we, as parents, have to trust our instincts. But I share this with you because I genuinely feel like it is helpful advice. I admit that the potential impact of my “lingering” may not have necessarily occurred to me. Exuding confidence in the face of a this new experience was incredibly challenging, yet it really did serve us well.

Ultimately I found it to be quite empowering for both of us. But be warned… it can feel quite a bit like ripping off a bandaid.

First days of school teachers

Disillusioned Drop offs

Here is a summary of what our first two weeks were like for us last year:

Day 1

Noah was so intrigued by the novelty of this new experience that he didn’t really notice my departure that first morning, despite my clear “bye honey.” He blissfully marched into the classroom and over to where other children were playing without a second glance my direction.

It almost seemed too good to be true. No tears? No protests? Gosh, I wondered if he was even going to miss me.
Cue MY tears.

Day 2

But by the second day he had wised up and I learned a hard lesson.

If they can walk, it’s better to let them walk inside. Because let me tell you – when your tiny toddler is clinging desperately to your neck and screaming “don’t leave me Maaaaamaaaaa” it’s not easy to put on a confident face as the teacher attempts to gingerly pull them off you.

Doing a hand off is much smoother. I learned to have Noah walk into the classroom holding my hand and then lead him confidently to his teacher.

Day 3 and 4

He started resisting EN ROUTE to school. As we walked into the building he would tell me he wanted to go home. I tried to distract him by asking about his new classmates and toys I knew he was interested in there. But I began to have major doubts about our decision to enroll him. I questioned whether he was mature enough to handle it. Whether he was ever going to acclimate. I wondered if we should pull him out and try again when he was a little older?

I cried in the parking lot every morning. Why was this so hard? What in the world was the first day of KINDERGARTEN going to be like?!

And then, just like everyone had promised, it got easier and easier.

My Best Tip for Sensitive Parents

Consider planning a Boo-Hoo Breakfast (or at least a boo hoo phone date!).

That first week or two of preschool drop offs can be rough all around. Especially if you or your child have a very sensitive disposition. For me, it felt exceptionally emotional. Having someone you can lean on for moral support during this time can be crucial to surviving those first days of school. On several different occasions I found myself sitting in the school parking lot crying to my sister over the phone about how hard this process felt all around. She was so kind and encouraging to me.

This year, I am making plans to meet up with another Mama who will be dropping off her “BABY” for the first time at preschool the same day that I am. We are calling it a boo-hoo breakfast date. The thought is that it will be nice to share the experience in solidarity over coffee and a big pile of pancakes. This is such a vulnerable time and having someone that relates to you and understands what you are going through is such a powerful way to connect.

So I encourage you to try this. Schedule a breakfast or brunch date with another parent that first week after drop off. Someone who is going through this at the same time, or even someone who has recently experienced it and can relate to you. Even if you just grab a coffee together – it can make such a difference. And if you don’t have time for a meet up, then plan to call someone that will support you, cheer you on, and offer up some solidarity.


A Helpful Song Recommendation

The thing that probably helped our transition the most of anything was the song: My Mommy Comes Back, by Hap Palmer. I’m not sure where I heard about it but I looked it up on iTunes and played it for Noah, unaware that it would become one of the top played songs of our household in 2018. Only to be outdone by every parent’s favorite… Baby Shark.

The best part of this catchy little song is that the words are easy to substitute. This was Noah’s FAVORITE thing to do for a long time. “My Mama comes back, she always comes back, she always comes back to get me” easily became “my Papa comes back” or “Sippi comes back” and occasionally even “the Mailman comes back, he always comes back”… you get the point. It was great fun for him.

We would play this song on the way to school in the mornings and sing it as we walked inside. It became a part of our ritual that I believe Noah found comforting and I am sure it will be coming back into our lives soon enough as the new school year is upon us.


Helpful Book Recommendations

Noah has always been a kid who really enjoys books. And in the past year we have discovered that Niko is quite a little book lover too. We have found books to be a great way to help introduce new experiences such as becoming a big brother and potty training. They have also been helpful in demystifying things Noah has been fearful of such as going to the doctor, bees, and thunderstorms. Naturally as school approached last year, I did some research to find a few books I hoped would help make the transition smoother for all of us.

Here are a few that were BIG winners at our house:

Llama Llama Misses Mama by Anna Dewdney is a wonderful book that tells the story of a little Llama who goes to a new school and experiences a difficult time transitioning once his Mama leaves. He gradually warms up as the day progresses with the help of his teacher and new friends. And before he knows it – his Mama comes back to get him! In the familiar style to other Llama Llama books, this story rhymes which makes it a fun and enjoyable to read as well.


Oh My Baby, Little One by Kathi Appelt (Author) and Jane Dyer (Illustrator) was another amazing addition to our home library during this time. This book tells the story from a Mama’s perspective as she reminds her baby that her love is with him throughout the day and in everything they do when they are apart. The illustrations are beautiful and in each part you can find the “love” hidden throughout the story. It also has a lyrical rhyme that is soothing and reassuring to read.

“Oh my baby, little one,
the hardest thing I do
is hold you tight, then let you go,
and walk away from you.

But even when I’m far away,
this love I have will stay
and wrap itself around you
every minute of the day.”


Bye-Bye Time by Elizabeth Verdick (Author) & Marieka Heinlen (Illustrator) is a board book that was also a great find. It is a simply written story that offers some straightforward rituals families can create. And it illustrates different tools that children can use to help ease the transition of saying “bye-bye.” In my opinion, this one is written so that even a very young child can understand it.


Another book that was recommended to me by several other parents is The Kissing Hand by Audrey Penn, illustrated by Ruth Harper & Nancy Leak. I really enjoyed the story but it was a little above Noah’s head last year when I tried to read it to him. This year I plan to pull it out to try again. Now that his attention span is a little more mature, I imagine it will become another favorite at our house.


After a couple of weeks, our morning drop off had found a really good groove.

First Days of School

Noah began to look forward to going to school and talked non-stop about all the children in his class. He told us about all of the activities they did at school and about how much he loved his teachers. I was reassured that we had made the right decision for him and for our family.

As we head in to another new year, I am thankful this will not be “my first rodeo.” But I have no doubt we will revisit many of the same emotional challenges as we transition into new routines with Niko as a first time preschooler and even with Noah this second time around.

I hope you found something here that may be helpful to you and your family as you head into these first days or weeks of school. Or at least that you know you are not alone during this emotional time. And if you have other tips or advice that helped your family, please comment below and share with all of us. For certain we can all be in this together.

Cheers to solidarity! And good luck to you all!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.