Kindergarten Empty Nest: When your Youngest Starts School

Last Updated on August 15, 2017

Most parents struggle when they send their first child off to Kindergarten. Sadness at the loss of unscheduled companionship, anxiety and apprehension are all normal feelings.

When my oldest, Keira, started school last September I remember missing her and feeling a little sad about the transition but I still had my youngest daughter Ava holding my hand, waiting to get out and do things. My days were still busy and it wasn’t long before Keira being at school felt like normalcy.

Now my baby, my determined little 3 year old is heading off to full-day Kindergarten in a few weeks and I’m left dealing with the emotions brought up with the thought of my baby climbing up those bus steps for the first time wearing a backpack bigger than she is. This time I won’t have anyone to hold my hand as the bus drives off.

Ava on the other hand couldn’t be more excited about finally starting school – despite the disappointment both girls felt when they discovered they would not be in the same class. She might only be three but she has been ready for school since Keira started and in fact has been completely irked the entire time that she had to stay home with me.



The transition to sending your youngest child to Kindergarten can be tricky but there are things you can do to ease the transition for both of you.

1. One-on-one time

The summer can be hectic, especially with your other children at home, and your youngest child may already miss the one-on-one time they are accustomed to. Go for a walk together, read a book, or simply cuddle – just make sure it is uninterrupted focused time spent with your child. When school starts you will want to keep up the one-on-one time. This time spent together will be reassuring to both you and your child – who is likely missing you after long days spent at school.

2. Plan your days

If you are a stay at home parent, take advantage of the opportunity to do things you may have been putting off. Start that class you keep thinking about, exercise more, finally have that clean house. You may also want to considering signing up to be a parent volunteer so you have a chance to interact with your childand their new friends in a different way.

3.Avoid after School  Activities

Starting Kindergarten is a huge change so let your child adjust before filling up their free time. They don’t need anything else to tire them out, especially if they attend full day kindergarten and you probably don’t need the added stress. There were days in the beginning where my oldest would come home and immediately climb up to bed for a nap. Kindergarten is busy and full days are long enough as it is for young children. You should also let your child get used to classroom rules before you throw them into a situation with a whole other set of rules to learn. Allow them the down time of just being at home for awhile before starting them into any new activities.

5. Prepare for School Together

Make special memories with your child and shop for new outfits and school supplies together. Head out shopping together and pick up a lunch box, lunch gear, and a backpack.  Make time to shop for that perfect outfit for the first day of school. Have fun trying on new outfits and let them pick out a few pieces themselves.  Build excitement for the big day and get them involved in the preparation for an easier transition.


I’m already working through these tips with Ava to get us prepared for sending her off to Kindergarten and it is already making me feel a little more ready for the transition.  In fact we just got back from a trip to Carter’s | OshKosh together where we not only picked out a fabulous first day of school outfit for Ava, but one for Keira too.



Can we talk about those leggings though? Aren’t they just too adorable and quirky and absolutely perfect?



Ava chose unicorn leggings for herself and we found a pair of cat leggings that we knew immediately Keira would adore along with matching shirts and headbands to finish off their outfits for a fresh look on their first day of school.



Going back to school shopping with my baby was a  truly bitter-sweet experience. On one hand I am experiencing sadness that we are here already but on the other hand I am excited for what this year will bring us and love how eager she is to head to school for the first day in just the cutest unicorn outfit ever.

Carter’s | OshKosh is a great destination for all your back-to-school shopping needs – whether you want to grab some stylish graphic tees and iconic OskKosh jeans or stock up on school uniforms for private or catholic school. The best part is that you are sure to have fun picking out fabulous outfits together that you will both love.


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Visit and enter for your chance to win one of three $500 shopping sprees to Carter’s | OshKosh and a professional family photoshoot! It’s easy to enter, just upload a photo of your child with the hashtag #MyCanadianCutie and submit the form.




Is your baby heading to Kindergarten for the first time? How are you coping?


Disclosure: I have partnered with YMC and Carter’s | OshKosh and have received compensation for this post. All opinions in the post are my own.


21 thoughts on “Kindergarten Empty Nest: When your Youngest Starts School

  1. I love Carter’s | OshKosh and am lucky enough to have a store close by. Absolutely beautiful clothes. Yes, it’s very important to start talking about school early so that both you and your child are ready when the time comes. I know one mum who did talk to her son about it but omitted to mention that school goes on for years, he was most upset when he had to go to school AGAIN the next day he thought he was finished after just one day. 🙂

  2. When my youngest went to kindergarten, she just waved to me and hopped on the bus. She was so ready. It took me a little getting used to. Just keep busy.

  3. It’s been a few years since our youngest headed to kindergarten, but I still remember it! Hugs to all the mamas out there with kiddos heading to kindergarten this year!

  4. I have a couple more years before Kindergarten but I’m saving this list for later. But I do love their outfits! Super cute. I think I need to pick up those leggings for my little one!

  5. Yes, my little princess starts Kindergarten on Monday! Where did the time go? I know she’ll do great as she is independent but I can’t deal… lol. Love those unicorn leggings!!

  6. Your kids are so adorable! Those outfits are so cute too. I would have loved to have those outfits for my girls.

  7. omg my GOSH your littles are cuties! My daughter adores cats and unicorns, I am going to need that “I’m Just Kitten” shirt for sure!

  8. Aww, it was tough when my kids first started going to school. I think your strategies are going to be really helpful though! Cutest OshKosh clothes ever!

  9. I remember when my youngest started school. It was so weird at first to have the day to myself again. Now they are both in College and the years have flown by.

  10. I remember when my youngest started kindergarten and now he is starting high school. Eeek. Your girls are adorable and I love their outfits.

  11. My twins start preschool next week and I’m in for a big change. We’ve started our morning routine and I’ve left the afternoon open for connecting and fun. I love the tip of waiting on activities until things become more familiar.

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