A Letter to my First-Born on his First Day of Kindergarten

To my little man –

In less than a week you will start kindergarten. It’s a day that Daddy and I have been anxiously awaiting since the doctor placed you – our little four-pound miracle – into my arms. When you were a baby, I would daydream about what you would be like when you grow up. What would you look like? How would your voice sound? What would you be passionate about? I would also try to imagine what it would feel like the first time you stepped foot inside your school and went off to kindergarten. I can’t believe that day has finally arrived.

Our little miracle

I don’t think I’ll ever be ready to see you walk through those big school doors all alone. You see, you were something that we dreamed of for years. You are a precious little miracle to us and the thought of letting you go makes me tearful. I will always hold a special place in my heart for you because you were the one that made me a mom. I try not to be a ‘helicopter mom’ to you and your brothers, but sometimes I can’t fight the urge to put a protective bubble around you so you don’t fall. We went through so much heartbreak to have you and I never want anything bad or unexpected to happen.

As we cuddled in your bed last night (like we do every night) we discussed what we will be doing next week. As I put on a brave face, my heart sank a little when I uttered the words “You’ll be going to your first day of kindergarten.” You smiled and sounded so excited to meet your teacher, see your new classroom, and make new friends. I, on the other hand, am not as enthusiastic. I know we’ve done all we can as parents to ensure your success in Kindergarten, but that still doesn’t mean I’m ready to let you go.

When I fell asleep all of these questions keep running through my mind. What new friends will you make? Who is going to comfort you when you get a boo-boo on the playground? Who is going to sit with you at lunch? Will you be embarrassed when your speech teacher pulls you out of class for therapy? Will you miss us?

I’m delighted with how far you’ve come during your four years of speech therapy. On your first day of preschool, you could barely say your name clear enough for the teachers to understand it. Now, you are talking up a storm. I hope that you hold your head high the first time your new speech teacher pulls you out of class for therapy. It’s not easy to be different, but you should be proud of all that you’ve accomplished.

I am confident you will love kindergarten. You are an excellent listener, a hard worker, an inquisitive and compassionate little man. I am amazed at what you have learned during these past six years, and I can only imagine what you will learn in the years to come.

My biggest pieces of advice to you as you start Kindergarten:

  • Be kind to everyone you meet. You never know what other kids are going through.
  • Make friends with everyone, especially that lonely kid in class. They could probably use a good friend like you.
  • Be yourself. I know it is easy to be shy, but you have such a fun and wonderful personality. Let that shine through and all of the kids and teachers will love you, just like I do.
  • Make good choices. I know it’s hard to not follow the crowd when they are breaking the rules, but I trust that you know the difference between right and wrong.
  • Be confident. Always stand up for yourself. I want you to be confident in your abilities and not second guess yourself.

You will have good days and bad days this year. Just remember that no matter what – Mommy and Daddy love you! I promise I will try and hold back my tears as I hug and kiss you one last time before you embark on this great adventure. I cannot wait for you to get home and tell us all about your first day. Even though I am nervous and a little sad to be losing my “baby,” the one thing I am sure of is that you are ready for this next chapter in your life.


We wish all the kids (and their mommies) who are starting kindergarten this year a successful and wonderful school year! For more well wishes, check out Tumkeen’s post Hellos and Goodbyes, A Letter to My Kindergartener.


  1. Awesome story, Stef. Your kids are so lucky to have such awesome and loving parents. I hope all parents will use your advice with their kids as they start school. By the way, rest assured, kids don’t pay any attention to the kids being pulled out of class for speech.

    • Thank you Barb! I really appreciate the kind comments. You are sweet. Thank you for the re-assurance about him being pulled out for speech. I’m hoping that is the case.


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