My Darling Boy,

You heard me pray over you, asking God to help you succeed in your first day of “big kid” school this year. I was proud of your insistence that you were going to learn something on the first day. I was proud of myself for being pragmatic, and walking out to the car with my head held high in confidence that you are ready for this new adventure.

When I pick you up, I will share with you a few things about our day: that your siblings and I didn’t do anything out of the ordinary. I will inform you that I had to call your dad to figure out the settings on the television that you have operated all summer long. I will giggle with you over your little brother learning how to giggle when you were at school. And, I will share my aggravation at the dogs being under foot while I made food, served food, and just did what they are best at doing – annoying me. I will share how your little sister told me she missed you, and informed me that “Chase is at school today.”

But, there are some things I will never share.

I will never tell you how, while I walked to the van confidently, that I choked back a sob when your siblings and I pulled up at the store where we have shopped all summer long – just the four of us, but today with only three.

I will never tell you just how many times I thought of you today. The number of times I thought of you, worried for you, and prayed for you are countless.

While your PreK teachers assuaged my fears last year, I will never share how I doubted your teacher this year, and her ability to nurture you the way you are accustomed.

I will never share how, as I watched your sister eating her lunch, I watched the clock change from 12:45, to 12:50, to 1:00 PM, and how time seemed to drag slower than the pour of molasses.

I will never share how I scoped out your classroom, school, and the surrounding fence line to evaluate for safety.

I will never share the doubt I had in my parenting skills—how I doubted having prepared you adequately for all the life lessons you will begin learning today and, every day hereafter.

I will never share how, although you may be ready for this new adventure, I am completely ill prepared for you to grow up.

There is truth to the saying, “The days are long, but the years are short.” The days of the summer were very, very long; yet, only last year, you were going to “school” for the first time. You succeeded in being away from your siblings and I last year, and I have confidence that you will continue to be successful this year.

I will never share that I am not ready to let you fly. Because, while you are my oldest, you will always be my baby.

Although I am not ready, I know you are ready. 

So, fly you must.

I know I must encourage your flight today and, every day. 

So, tonight, we will celebrate the completion of your first day of big kid school. I will share that I missed you terribly, but prayed for you a lot. I will ask you questions about your new schedule, your new teacher, and whether or not you made some friends.

I will watch you tackle today’s adventure, and all the adventures to come through the years, with a sense of pride and eagerness. But, as I learned today—there will be a catch in my throat each time you show me just how big you are getting. 

And, while I can’t let it hold you back, I will embrace the quiet hesitation I feel, and place you in the palm of our Creator’s hands.

I am not ready for you to grow up, but I am ready to watch you fly, because with every breath I take, I can feel you were made for something great. I won’t be able to hold you back, because you and your peers are needed to make a change in this world. 

Allow your mama a moment to breathe and let go…

Don’t look back or behind you as I release your hand.

Take flight.

And, fly, my darling boy.

Fly as high as you can go.

You might also like:

My Heart Was Waiting For A Son

Mothering Boys is a Work of the Heart

Dear Son, You Will Always Be My Little Boy

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AnnAliese Harry

AnnAliese is a proud Army wife and mother to two young children. She has a BA in History, a Masters in Social Work, and has worked extensively with children and families in both clinical settings and as a case manager. Since the birth of her children, she has taken a hiatus from paid employment, and devotes time to volunteering at whichever military chapel the family attends. She currently blogs about topics of faith, parenting, and military life at You can follow her on Twitter, on Instagram or on Facebook at A Beautiful, Camouflaged Mess of A Life.