helping your little one transition into the new school year

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eleanor and samson on their first day of 1st grade and kindergarten, two autumns ago in 2017.

eleanor’s first day of kindergarten in autumn 2016. 

samson’s first day of kindergarten, 2017. 

eleanor and samson’s first day of second grade and first grade, 2018. 

and below, eleanor and samson’s last day of second and third grade,2019. 

helping your little one transition into the new school year…

next week, schools in new york city (and lots of schools everywhere) begin up again! we have had a countdown going over here the last few months because conrad is beginning kindergarten and he has been so ready for september to roll around so he can follow in his big sister’s and brother’s foodsteps by joining them at school. while i know he is so ready, and that the transition should be smooth for him considering he has been at most school drop offs and pick ups for the last several years and just wants to do everything his older siblings are doing, i know how touch and go those first weeks of school can be for not just the little one, but also for the parent (been there!). i thought i’d share a few of the things we have done over the last few years that have made the transition easier on everyone, and i hope it’s a helpful read for anyone sending their little ones off to school for the first time, but also any grade or level this coming year!

  • getting into A SOLID ROUTINE ABOUT A WEEK BEFORE SCHOOL BEGINS. structured bedtimes and morning routines that fit the timeline of what your mornings will look like for the coming school year) can help everyone during those first few weeks back. especially if the clock has shifted during your summer vacation and bedtimes have been pushed back and morning routines kind of vary. it’s nice to get everyone back on schedule so we can start the year fresh and your little ones know what to expect in their home routines.
  • we have a PUMP UP PLAYLIST WITH OUR FAVORITE DANCE PARTY SONGS and we love rocking out to it all year but especially this time of year as we all benefit from some upbeat music and fun lyrics. i also really believe in the power of movement and i know when we all start jumping around and dancing, it can calm everyones nerves faster than many other things.
  • i believe in the power of one-on-one time regularly with each child individually, but especially during their first few weeks back in the classroom. if you can, SCHEDULE A SPECIAL DATE without any other siblings or distractions and put it on the calendar for a few days after school begins so you both have something to look forward to. it’s a great time to chat face-to-face over a treat or activity and hear all about their new classroom and friends, what they have enjoyed so far or what they don’t love just yet about their new environment. i know for eleanor during her first few weeks of kindergarten, there were a lot of things she did not like and i grew very worried as the days went on and she felt really bothered by certain things. i remember i didn’t have great solutions for her on the spot (a lot of it was just new routine she needed time to adapt to) but i wanted to make sure she knew i was hearing her and could understand her frustration by making a point to say things like, “that must be really annoying when that happens. i can see how that would make you feel that way. i’m so sorry.” sometimes just knowing you have an ally and someone on your side is all you need in those moments of trying to be brave in a new environment.
  • it’s great to do frequently, but making a point to BUILD THEM UP AND POINT OUT THEIR STRENGTHS (almost as super-powers) as they prepare to spend time away from you can help them in moments when they might be nervous or miss you. we love this book called the kissing hand, which gives your little one a great visual to think about during their day away from you when they might need a reminder that you’re still right there in a special way. it’s especially appropriate for those with preschoolers and kindergartners leaving you for the first time. also, i’ve blogged about it before, but this book called oh, the places you’ll go! is classic and especially fitting during this time of year.
  • it doesn’t have to be fancy, but SURPRISING THEM on their first day (or maybe a few weeks in if needed) at pick up time WITH A SPECIAL TRINKET OR NEW BOOK OR TOY has been something we have done. it just makes the day feel a little more special and who doesn’t love a fun surprise wrapped in wrapping paper!?
  • our family dedicates an evening before school begins to celebrating our kids and their coming year by giving them A FATHER’S BLESSING. this is something faith-based that we do, but i know there are other things you could substitute for this. one thought that comes to mind is HOLDING HANDS IN A CIRCLE WITH YOUR LOVED ONES and everyone going around the room and sharing something they know your little one will do really well this coming year or something they are excited for them to learn.
  • a tradition josh started when eleanor left for kindergarten and has carried on consistently with nearly each and every packed lunch is WRITING A HANDWRITTEN NOTE WITH A POSITIVE AFFIRMATION.  even before they could read, we send these along in their lunches and their teachers helped them read them until they could begin sounding out their letters and words and putting the sentences together themselves. things like, “eleanor is a good friend” or “samson is a talented artist.” we started doing similes as they started learning about them, too. like, “samson is brave like a lion” or “eleanor can run as fast as lightening.” always signed with love by mama or papa. both our kids have loved coming home and telling us what their lunch box note said!
  • this sounds like a no-brainer, but i really truly believe HUGGING AND KISSING AND GIVING CONSTANT AFFECTION to our little ones goes a long way and can help build their confidence and self-esteem for harder moments like transitioning to a new classroom or school. i am sure my kids will cut off my long hugs and kisses soon, but until then i will keep dishing them out as often as i can because it’s something i really believe in.
  • BE POSITIVE! BE HOPEFUL! BE OPTIMISTIC! (OR AT LEAST ACT THAT WAY IN FRONT OF YOUR KIDS). this isn’t just for you. your kids will pick up on your feelings and mood, and if you are acting anxious or sad about their return to school, then they will sense that and channel those feelings.

this time of year is so very exciting! at the end of the day, even if there are tears and it feels as hard for you as it does them, they will be just fine! they’re in wonderful hands and this milestone is going to be a fun one to look back on. i have such tremendous respect and love for the teachers we have encountered so far over the last few years that have given so much of their time and talents, love and compassion to my babies. your kiddos have this! and so do you! good luck to everyone in the next few weeks!

if your family has any special traditions or additional tips to help make the transition smooth sailing, please share them in the comments below so everyone can benefit!

  1. Adrianna

    In my family we had lots of school anxiety. Luckily we lived by the beach so every morning my mom would have us all walk down by the water. Everyone thought it was so nice but poor mom was just trying to calm a lot of nerves in three little bodies (even in the colder months).

    She also tried to calm nerves with music. Back then it alternated between a Backstreet Boys and nysnc cassette. Definitely appreciative of Dad for putting up with that one!

  2. emily

    Thank you for this. As a parent of a new kindergartener, it helped to read about your experience and your wisdom. I value your words as a mother so much.

  3. Taylor

    I have to say as a former elementary educator, it truly wonderful to see that you take individual time with your kids to listen how their day went. And with little kiddos! It is truly admirable! Wishing you guys a wonderful 2019-2020 school year!

  4. Monique

    Thank you for this insightful post to helping our kids transition well into school. Our first kiddo is starting Kinder this year and we moved states this summer, so much transition for Gwen to process and take in. I’ll definitely use these tips before she starts in two weeks. I love the father’s blessing idea, we will definitely be doing that. Our friend did that with his kids and he gave them 3 L’s as a part of it. Be a LIGHT, LOVE others, and LEARN

  5. Yaindy Lara

    This are great tips! I have 3 kiddos, one is starting middle school, 2nd and kindergarten. I am so excited for them and can’t wait to hear everything about the stuff they have learned. Hope your kiddos have a great school year :)

  6. Kelly

    I love how you document your kids lives, they are going to love reading these posts back when they are older!

    xx Kelly
    Sparkles and Shoes

  7. Karen

    Great advice! and make the most of these times – my ‘kids’ are all grown and left home now. Love these memories!

  8. Megan

    I’m a kindergarten teacher – these are all great suggestions! :-)