Sending Your Oldest To Kindergarten: Learning to Let Go

My Son is Going to Kindergarten: Learning to Let My Baby Leave the Nest | Twin Cities Moms BlogHave you ever had the privilege of watching a mother bird set her babies out to fly? I was able to watch a little baby bird learn to fly this summer and it really struck a chord with me. There was this little robin hopping around on the table we have out on our deck. It was a peculiar little thing, behaving unlike any other bird that I had seen before, and there it was, flutter, flutter, fall and hop hop around the table; over and over again. I could not for the life of me figure out what this bird was doing. Then I noticed her. There, on the other side of my deck sat the Mama Robin watching. She was watching her baby learn how to survive life outside of her safe nest. She wasn’t by her baby’s side, coddling him as he tested out his wings. No, she was a short distance away, letting him figure it out on his own. Sure, if he ran into trouble she was able to be there but until then she sat watching him ever so carefully. It’s something that a robin has to learn how to do, right? You never see mature robins hanging out in Mama’s nest now do you? That’s when it hit me: My son is going into Kindergarten and leaving my nest.

Suddenly, out of nowhere, I have realized that  my “baby” boy, my firstborn has grown up. How did this happen? I was told that it would happen: that all children grow up too quickly. I guess I didn’t believe it or at least I couldn’t fathom how this milestone of Kindergarten would feel. I’ve enjoyed our days spent together for the past five and a half years; days where he chatted my ear off with random thoughts and days where he incessantly irritated and equally loved on his little sister. My house has been anything but quiet since he entered my world and the quiet is something I’ve longed for since that cold day in 2008.

Am I really ready for it? Am I really ready for him to be gone at Kindergarten all day long, every day? The answer is very bittersweet.

  1. I’m excited to have some focused attention on my two little girls: one is three and the other was born this past May. But…
  2. My son and I have such a bond with each other that I cannot imagine a day, let alone five days, where he’s not by my side talking my ear off. Don’t get me wrong, since I had my youngest daughter this past May, I have longed for quieter days and looked forward to my oldest entering into Kindergarten. Maybe I could actually finish a conversation on the phone with a friend? You know how kids are when you’re on the phone and my son has got to be the worst. The second I’m on the phone he’s like a moth to a flame: instantly at my side asking me for a snack or to watch TV or to have a friend over or to…
  3. I won’t hear the common, “Mom, I’m bored” comments all day long or “Mom, why can’t we have another playdate?” Those questions, the ones I feel like I’m answering hourly will be gone starting Tuesday, September 2nd. The closer we get to that day the more emotional I find myself becoming.
  4. I’m sad about the innocence that he has now and what will be lost once he enters school. He’ll have outside influences: new ideas, new friends, new authority figures. The safe, little bubble that I’ve worked so hard to create here at home is going to begin leaking, just enough so that he can start the process of growing up away from my nest.
  5. My son still adores Thomas the Tank Engine and I’ve often wondered as I watch him play with his trains if he’ll still love that little blue engine as much after he finishes Kindergarten. Once I start thinking about that I begin to worry about whether or not he’ll fit in. Will the other kids tease him because he still likes Thomas? Should I try to introduce him to other characters to help him not be socially unacceptable? I mean is it still okay to like Thomas once you’re in Kindergarten?

My Son is Going to Kindergarten: Learning to Let My Baby Leave the Nest | Twin Cities Moms Blog

It’s the “what ifs” that are driving me crazy; knowing that I’m not with him to help him through the day. Because, you know, I’ve done this school thing before. I know how to handle Kindergarten. I know how to do middle school and high school. I know how to be confident in who I am and I can do that for him in school, right? It goes against my motherly nature to let him go off into the world of school on his own. I kind of feel like I’m Mama Robin, pushing her baby out of the nest to fly. How are mother birds able to do that? How are they able to push their babies out of a nest, one that’s in a tree, and hope they’ll spread their wings and fly?

I know that this is only one of the many times I’ll need to let one of my children go out on their own. My head understands that this is necessary. In order to succeed in life my children must leave my nest but that doesn’t make it any easier. My heart still hurts when I think about that first day of Kindergarten. It aches for the closing chapter of my son’s first part of life. The simple days: The snuggle days. The nights where the Boogie Man is in the closet and only Mommy and Daddy can protect him. The lunches of macaroni and cheese and fruit snacks. The lazy mornings when we had no place to be so we stayed in our PJs and watched PBS Kids. The afternoons where I was his only playmate, his best friend, the coolest person he knows. That chapter is closing now and a new one begins.

A new beginning of studying, learning, and navigating the social world of elementary school. A new start filled with sports teams, extracurricular activities, school programs and parent-teacher conferences. It really is exciting to watch him grow. So while I’m certain that I’ll be doing all that I can to hold it together that first morning of school, I know that as soon as I leave him with his teacher and walk out of those school doors I’ll break down. I’ll break down for all of the reasons I shared with you above, the loss of this part of my first baby’s life, the absence I’ll feel when he’s not with me during the day, and knowing that this is all part of pushing him out of nest. Pushing him out so that he can learn to thrive.

And so, until that day I’m going to soak in all that I can. Then I’ll take my spot like that Mama Robin; watching ever so carefully from the side.My Son is Going to Kindergarten: Learning to Let My Baby Leave the Nest | Twin Cities Moms Blog

My son always does better with transitions when we talk about them and books have always worked really well for us. My sister tipped me off on the New York Times bestseller by Audrey Penn, The Kissing Hand. It’s a sweet book and has been helping both of us get ready for that fateful first day. I’ve also read these books and love them as well. Hyewon Yum‘s Mom, It’s My First Day of Kindergarten is one we read over the summer after we got it from the library. I like it because it addresses how the little boy is excited for Kindergarten and how his mom is sad and then it switches where the mom is excited and the son is nervous. Brennan really loved reading it too; I think he liked knowing that this wasn’t going to be easy for Mom either.

My Son is Going to Kindergarten: Learning to Let My Baby Leave the Nest | Twin Cities Moms Blog

How are you feeling about the school year starting? Any school milestones your kids are coming up on this school year?

Elizabeth "Bert" Anderson is a stay-at-home mom of three living outside of the Twin Cities in Rogers. She writes a blog where she honestly chronicles the peaks and valleys of parenting. Even though she has more than one child, Bert maintains that whether you have one child or five, there's a first time for everything. She's a lover of cloth diapers, pop culture, healthy living and fitness.


  1. My sentiments exactly! I had started expressing my feelings on my blog with many of the same thoughts and questions. Particularly that loss of innocence, not being there to navigate with them and even the interest in Thomas and wondering if that would create social difficulties. Thanks for sharing your like-minded feelings so beautifully.

    • Thanks so much, Britta! They can’t stay little forever….hopefully they’ll both come out loving Thomas at the end of the year, right?

  2. Your post is so beautifully written. This is where I am at right now and it’s so hard. But your post helped me to understand and see that this is necessary to let them grow up. Since my son started kindergarten last week I played with the idea of homeschooling him, but it feels like I might only postpone what’s going to happen anyways and also has to happen! My heart aches everyday right now!


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