the countdown to kindergarten begins... GRAND ways to support Littles we 🩷!
- May 29
- 9 min read
Updated: 6 days ago
Friday, May 29, 2026
While May and June are often filled
with caps, gowns, and graduation parties,
some of life’s sweetest milestones are actually happening quietly
as others get ready to begin their own school journey!
Many young families are realizing the same thing…
Kindergarten is just around the corner!
This is true for Laurie and her family as they near the beginning
of such a special adventure!
While we know many families are busy thinking about graduation and all it holds,
we’re spending our time today
sharing ways to support and encourage our youngest learners this summer...
And we're adding our own GRAND spin to things, of course!
The countdown is officially on!
It's hard to believe, but in just a few short months, little backpacks will be zipped, lunchboxes packed, and brave little feet will walk into a brand-new season of learning and growing. It’s an exciting transition filled with BIG feelings — for Littles and the grown-ups who love them.
And while parents are often busy preparing for this next step,
we GRANDS have our own unique opportunity
to cheer on our Littles and their families in subtle yet meaningful ways!
Okay!
I’m not exactly sure how this happened…
How is this precious Little headed to kindergarten in the fall?
If I’m being honest though,
this Grammy has been looking forward to this moment for a very long time!
Ever since Little D made her entrance in 2021,
I’ve been excited to watch this journey unfold for her.
And as a retired kindergarten teacher, I know firsthand
just how much adventure, discovery, and fun await in the years to come!
The months leading up to kindergarten are important because they serve as a bridge between early childhood and a brand-new stage of independence, learning, and growth. During this time, children are developing not only academic skills — but, more importantly, they’re building confidence, motor skills, emotional readiness, routines, and the social skills that help them feel secure stepping into a classroom community. WHEW!!! That's a lot to take in!
As retired kindergarten teachers,
both Laura and I have the unique perspective of knowing first hand
which skills and experiences can help Littles feel confident and prepared
as they take these first steps between the small, familiar world of home
and a much larger, structured community.
Below is a checklist of important skills we've compiled!
PLEASE KNOW… these expectations are simply general guidelines!
Children enter kindergarten with a WIDE variety
of personalities, experiences, strengths, and skill levels.
The truth is every child develops at their own unique pace!
For many children,
kindergarten is one of the first major transitions
they truly remember!
The support and encouragement our Littles receive beforehand as well as any opportunities they have to practice routines can shape how they view school, and themselves as learners. When trusted grown-ups cheer them on, our Littles begin to believe, “I can do this!”
This summer, I’ll be doing all I can
to support and encourage our Little D and her parents!
If you live near your grandkids, the final months “before kindergarten” are filled with moments to do the same as your Little gets closer to the day school begins!
Live far away? Distant GRANDS can still be a cheerleader!
In the weeks leading up to the big day,
check-in regularly via phone calls or FaceTime visits.
When doing so, give some of the ideas we’re sharing here a try
and adapt them to fit your family’s needs!
GRAND Ways to Support Our Littles!
In no particular order, here are the
Top 9 Ways
I’m helping my own future kindergartner get ready for what's ahead!
#9 - Give your Little a set of school supplies to use all summer! This way, they can practice using the materials correctly and putting them away carefully! Cutting with scissors, using glue or a glue stick and practicing writing words or their name with a pencil will build confidence! And, of course, good luck keeping track of those crayons!
#8 - Provide opportunities to problem-solve whenever possible! Talk through simple “what if” situations together — like what to do if they can’t find something, don’t understand directions, or need help during an activity. Helping them learn to ask a friend first and then seek out a trusted adult when needed can build both confidence and independence before kindergarten begins.
#7 - During the summer months, spend time on your Little’s future school playground! Spend time playing on the equipment and role play possible scenarios - lining up to go inside, what to do if you need to use the bathroom, asking a friend to play, what to do if you or a friend need help. Walk around the outside of the building and point out - this looks like the lunchroom, the gym, the main office.
#6 - Provide opportunities for your Little to practice using life skills independently! Be sure your Little can use the bathroom by themselves! Speaking from experience, kindergarten teachers will NOT help wipe little bottoms! Similarly, have your Little practice tying their shoes, zipping their coats and their backpacks. Practice opening packages and containers such as goldfish packets or lunchbox storage. And… Don't forget to give Littles opportunities to be responsible and practice cleaning up after themselves when eating, playing or doing projects! Encourage Littles to play by themselves for 10-15 minutes without input from you!
#5 - Talk positively about the exciting experiences that awaits your Little! Share what you are excited about for them to experience — making new friends, meeting caring teachers, discovering favorite library books, learning new things, and becoming part of a fun classroom community are some of the fun moments your Little has to look forward to!
#4 - Play games or plan activities to build learning skills! There are many ways you can do this, including these favorite ideas!
Rhyming Games! Play rhyming games together throughout the day to help your Little begin hearing and recognizing word patterns. Silly exchanges like, ““I know something that has a tail and rhymes with mat?” or playful made-up rhymes during car rides, story time, or meals help build this important early reading skill!
Letter Names/Sounds Games! Point out letters in books, on cereal boxes or on signs or in books.. Play I Spy “I spy something that begins with /sss/” Looks for letters out the car window. Make up silly songs to any tune - “Kindergarten starts with /k/. Yes it does, yes it does. What else begins with /k/?”
Listening Games! We all know that Littles will need to listen when they get to school and they’ll be much more successful when they get there if they can follow simple directions (ones with one or two steps). Playing Simon Says or Telephone or doing a listening activity or drawing project will give Littles needed practice for what’s ahead!
Everyday Math Experiences! Use measuring cups or a measuring tape, practice counting forwards and backwards, look for shapes in your world or play simple games with playing cards or dice. All of these experiences reinforce your Little’s understanding of numbers around them!
#3 - READ! READ! READ!
Read books with your Little whenever you can and encourage them to look at books independently, too. As the start of kindergarten draws closer, spend time reading picture books about school together to help your Little become familiar with all that awaits!
#2 - Littles love to hear childhood stories about their moms and dads and we GRANDS are a great resource for such tales! This is a perfect time to share stories about your Little’s parents’ first days of school including your memories of what they worried about or what they loved. In fact, include memories from your own first day… if you can remember that far back, that is! Show your Littles pictures of their parents’ kindergarten year or first day.
Little D’s mom on her first day of kindergarten, September 1996!
#1 - Be sure your Little knows that you believe in them! Let them know they will do great things because they are smart, kind, strong, brave, curious and… So much more!
GRAND Ways to Support The Parents!
We can’t forget about Mom and Dad…
For many parents,
kindergarten marks one of the first big reminders
that their little one is growing up!
As exciting as the transition to kindergarten can be for our Littles, it can also bring a mix of emotions for their parents. The months leading up to the first day of school are often filled with excitement, anticipation, questions, scheduling, preparations, and sometimes even a few worries about whether their child is truly “ready.”
Some of the greatest gifts we GRANDS can offer during this season
is simply being a steady presence
not only for the Littles beginning kindergarten,
but for the parents guiding them there!
These are the gifts we can readily share!
🩷 We can offer our ENCOURAGEMENT!
🩷 We can provide needed SUPPORT!
🩷 We can be a safe place to LISTEN!
🩷 We can CELEBRATE this milestone!
Remember, there’s always power in simply reminding Mom & Dad
that they’re doing a good job
and that you are proud of them and love them!
🩷 🩷 🩷
This countdown period truly matters!
The months leading up to any new school experience
- and, most especially this first one-
gives Littles time to become familiar with what their new world will look and feel like.
Our advice… Start early!
Simple experiences like the ones we’ve offered in this post
can help ease any worries that arise
while also helping our Littles feel proud, prepared, and eager for kindergarten!
Our Littles love their routines and while doing things over and over for us feels mundane,
for them it brings a needed sense of security!
And, finally,
if faith is an important part of your family life as it is for us,
remind both your Little and their parents
that you’ll be praying for them as they prepare for this exciting new chapter.
The transition to kindergarten can bring so many emotions — excitement, anticipation, nervousness, uncertainty, and joy — and prayer can be a beautiful way to surround the entire family with peace, comfort and encouragement.
Pray for…
a smooth and positive start to the school year,
for good teachers, new friendships, and a growing love of learning.
Pray that your Little feels safe, confident, and supported
as they adjust to new routines and experiences.
And don’t forget Mom and Dad, too!
This milestone can bring a lot of emotions to the surface
as they watch their child take this giant step toward independence.
Sometimes one of the most meaningful things a GRAND can say is simply, “I’m praying for you.” Those words remind both Littles and their parents that they are deeply loved, supported, and never walking through this season, or any other, alone!
Do you know a Little who's headed to kindergarten soon?
Have you had experience doing so as a GRAND?
If so, we’d love to hear more…
Feel free to comment at the end of this post!
THANK YOU!
We’ll be back next week with a new post,
We look forward to recapping our month of May with you all!
It's been a busy one... we're still catching our breath!
We hope you’ll come back and join us then!
Don’t forget that you can always find us
We’d love it if you stopped by to check out our latest posts!
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In these coming months, as one school year winds down and we begin to gear up to another one beginning, it's equally important to remember that kindergarten is so much more than backpacks, pencils, and learning letters and numbers.
There’s a reason the book All I Really Need to Know I Learned in Kindergarten by Robert Fulghum has spoken to so many people over the years — because, just as we both know so well, many of life’s most important lessons truly do begin in kindergarten!
So, whether someone is graduating, beginning a new career, becoming a parent, retiring, or stepping into another new chapter, the qualities that matter most are often the very same ones introduced during those early childhood years. Kindness, respect, perseverance, curiosity, and learning to work with and care for others are lessons that never stop being important.
Perhaps that’s why kindergarten feels like such a meaningful milestone. In many ways, it marks the beginning of learning not just how to succeed in school, but how to move through life itself.
SPECIAL THANKS TO THE FOLLOWING SITES FOR FEATURING OUR POST!
A Morning Cup of Joe from The Cottage Market
Love Your Creativity from Life & Linda
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So very special. You are definitely hands on with your littles. I am happy to feature your Countdown to Kindergarten at Love Your Creativity.
Oh, I'm so happy for Laurie! It's been many years since my grands started Kindergarten, but I remember reading to them from the beginning and working on numbers. I actually started singing the times tables to my oldest granddaughter when she was less than a week old. I figured singing them would get them stuck in some part of her brain for use sooner or later. I also told my grands stories using big words so they'd have big vocabularies. I love all these activities and the prayer. Have a wonderful summer getting little Miss D ready for the excitement that awaits her!
https://marshainthemiddle.com/
I am so excited and happy for Miss D! KIndergarten is such a wonderful beginning to a life of academics-we never stop learning do we? I have wonderful memories of my kindergarten days and I'm in my 70s. Your guideance in this post is wonderful, and will also be of help to many parents and grandparents.
Thanks again for stopping by and for all your kind words....Great post ! Thanks for sharing all your expertise with us...
Hugs,
Deb
Debbie-Dabble blog
Aww! What an exciting time. I remember when my girls started nursery, I was so scared for them but at the same time excited. What great tips, advice and such a lovely post.