A Letter to My Son on His First Day of School


Dear Little Dude,

You are precious to me. Each year about this time, my heart swells with pride as I watch you put on your tennis shoes and grab your backpack for the year’s first day of school. And my mommy heart is excited for you, and anxious with you. I know this year, like the last two years I’ve sent you off to preschool, will bring another huge growth spurt, so many things will be learned, so many new experiences will expand your horizons.

As I drove you to school, my insides twisted up with mixed emotions about starting another year, you said, “Mama, I’m nervous. What if my teacher doesn’t like me?” I wanted to pull over and hug you. Part of me wanted to cry and comfort you and tell you it will be okay, another part of me wanted to smile and tell you all the million reasons why your teacher will like you!

I watched you for a moment after I dropped you off. How you used your walking feet and went and sat calmly down on the reading rug. Your face a big bright smile, your big blue eyes so kind. And I choked at how these small things are huge victories for us. How 2 years ago, these small things were so hard because we didn’t know what was going on. And I said thanks to God for you and all you’ve already overcome. And then I left you to enjoy your first day at school.

Little Dude, as I send you off, let me remind of you of what you bring with you that will help you along the way . . .

First, you are responsible. When I put you in charge, you always follow through, even if imperfectly, I can trust you to try. And more often than not, you exceed my expectations. I love how you surprise us all with what you can do. I hope you never stop doing that.


You have the most helpful spirit. I love how you always volunteer to be a helper. Just remember that helping means doing what the other person asks, and not what you want to do. Keep this in mind, and you will continue to be a blessing to those around you.


You have the energy! Some days I wish I could borrow some of your exuberance! You have a way of revving people up and getting us all excited about a new game or a special outing. You are charismatic and others want to be around you. Your excitement is contagious. Use your energy to encourage others to do what’s right, and you will be one heck of a leader someday!


Finally, you are an encourager. I love you how tell others when they are doing a good job. There are some words not worth saying. Leave those in your head. But a word of encouragement is always worth saying out loud. If you use your words to lift others up, you have friends wherever you go.


So when Mama’s not around, remember that you carry within you the tools to succeed at whatever you try. Don’t look at your struggles as obstacles, but instead as opportunities for God’s power to make you strong. And how much sweeter the reward when you work hard and overcome, as you continue to do.

Look at these unique qualities you have. Isn’t it amazing how you were made? I marvel in you all the time. And I marvel in you now.

Happy first day of school sweet boy. I love you.

Love, Mama



3 thoughts on “A Letter to My Son on His First Day of School

  1. What helpful and insightful comments. I hope you find ways to tell him these things over the course of each day. It will be of great encouragement to him, and you!

  2. Oh, that was so precious! Lil Dude is precious, Lil Man is precious, and so are you! You’re all doing such a great job at living and loving! Love you all!

  3. This made me want to cry it was so sweet. What a beautifully written letter! Lil Dude HAS come so far! I’m inspired by your patience and perseverance.

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