To My Little Boy, On Your First Day Of Kindergarten

My Sweet Boy,Inclass_copy

Everything about you looked so big to me this morning.  Those hands that used to barely fit around my finger nearly filled my entire hand as we walked down the hall.  Those shoulders that used to hunch up against my chest seemed so broad as you proudly carried your new backpack.  And those sweet brown eyes that used to spend hours scrunched in colicky anguish were round and bright and full of anticipation at what awaits you.

You had only a brief moment of hesitation before you ventured into your classroom.  I saw the momentary uncertainty flash in your eyes as you let go of my hand.  But I reached down and kissed your cheek, and I told you I’d stand out in the hall for a minute or two if you needed me.  “I’ll be right here,” I whispered.   That was all you needed–you bounded forward with confidence, never looking back.

This is as it should be.  Your eyes should be ahead–watchful, ready to learn, eager to take in all life will bring you.  My eyes are looking ahead too, realizing that this big step of independence you took this morning will be followed by many.  Lost teeth, too-short jeans, a deeper voice and first dates…each bold step will take a you a step further toward manhood, and further away from me.

And with bittersweet joy in my heart, I tell you, my boy:  Go.  Step into each new life experience with the same eager expectation I saw on your face this morning.  I trust the One who made you to steer you just where He would have you go.   I can’t wait to see the man He will shape you into.

But when the adventure gets bumpy, whether it’s a skinned knee in kindergarten, a bruised ego in 5th grade or a broken heart in college, just point yourself toward home.  I’ll be right here.

This post was originally published on August 17, 2006.

56 thoughts on “To My Little Boy, On Your First Day Of Kindergarten

  1. AmyG says:

    Aww, your post brought tears to my eyes. I’m already a little to emotional, having to let my little girl get on that big scary yellow bus. Last year, I was lucky enough that she didn’t have to take the bus, but I didn’t luck out this year. *sigh* I hope your little boy has an awesome year!!

  2. Melissa says:

    That just made me cry!! My oldest started kindergarten last year, and I cried ’til December. Now if I can handle the 1st day of 1st grade next week……

  3. Mrs. Who says:

    Great post! I just witnessed all our kindergarten parents letting the kids walk in alone this morning, after we had two days of letting the parents walk them to class. There were a few tears – mostly from the parents!!

  4. Lynette says:

    Ok…Bawling. I am sending my first to kindergarten in 2 weeks and 4 days and I am a mess. I know that He is in control and I know that I have done her well, but that doesn’t mean my heart isn’t hurting to see her go. This post was so beautifully written–thank you for sharing it.

  5. LifeatTheCircus says:

    This one gave me goosebumps… my oldest is starting preschool this year… just 3 mornings… 2.5 hrs a day.. and while I can list for you all the reasons why I know this is the right choice for him for this year and for the family…it still makes me cry as I think about sending him off. How thankful I am that “the One who made him will steer him where he wants him to go” how hard it is to let him go though.

  6. Sandi says:

    I Read this this morning and it hit home with me and I cried. My son is a senior this year. We have done the senior pictures and he is excited about graduating. It seems like yesterday I held his tiny hand and walked him in the Kindergarten. Now he is six foot tall and a very handsome young man. Almost ready to go out into the world where it is harder for us to protect them. I pray our prayers will suffice!! God Bless your family!!

  7. Mozi Esme's Mommy says:

    “I’ll be right here.” My sentiments exactly. Maybe my baby isn’t in kindergarten yet, but she is becoming more independent every day. And I’m glad to see her grow, but I do so miss her.

  8. randel says:

    oh lordy. my daughter starts kindergarten on monday, and my emotions are so mixed! part of me is really sad, and i tear up everytime i think about it. crazy!
    thanks for the post. you speaka my language!

  9. Carrie of Ceaseless Praises says:

    Waaaaah! I can’t imagine sending my boy to kindergarten, and I’m sure I’m holding on to him WAY too tight, but really, he’s only 8 months old, and if anyone even mentions the words “kindergarten” or even “first birthday”, I think about crying! What a sweet post!

  10. threeundertwo says:

    That was so sweet. I cried why mine started Kindergarten. I thought it was just evil that the PTA hosted a coffee on that first morning of school. Some of us saps had red eyes.

  11. Jessica says:

    I’ll have to come back to this one later. I couldn’t even read it right now…my oldest goes to Kindergarten in a few weeks.

  12. Diane says:

    Oh that brings back so many memories for me my little girl is going into grade 5 yikes .
    I was bawling under my sunglasses see her go.
    It was so emotional for me her she was ready and really never hesitated just bounded forward.

  13. La says:

    WOW…crying right now. I have been thinking about kindergarten for my little boy, he is almost 4 and I know it will come too soon. He will be going to a school further away from the daycare he is at now so that means making new friends and not seeing any familiar faces. So, this is what it is really like? I don’t know if I will be ready for this. Sounds like you were a trooper this morning as was he!!

  14. mamajil says:

    Oh wow I have tears in my eyes…the years go by so fast…my oldest son was 5 not long ago and now he is grown and married….thank goodness I still have 9 more chicks in the nest none the less this post made me think on how fast time flies!!
    I hope he has a great first day!!
    This was a beautiful post!

  15. Sarah @ Short Stop says:

    Oh my, Shannon.
    You perfectly captured the emotions of my heart, as I raise my three boys. My oldest starts pre-K in a few weeks, and you couldn’t have summed up my feelings any better.
    I love this letter.

  16. Nell says:

    So beautiful. I will be travelling this road in one more year. It’s too close. I don’t know how I’ll hold back my tears. Just as I couldn’t as I read this.

  17. bethany says:

    aww. your post got me all choked up. “We” start our first day of school on the 27th, and I’m so not ready for it. sniff…. sniff…. especially now.

  18. Jami says:

    Oh Shannon – I want to cry. My first baby goes to kindergarten in 6 days! It’s been a lot harder on me than I thought but she is so excited! I’m excited for her but sad too as this marks a very big step of independence! All good but not easy.
    Thanks for the post!

  19. Tiffany says:

    Precious, precious, precious… remind me of the way I write to my little guy. Just posted a letter today to him as you turned 16 months. Sometimes I feel I can’t breathe I get so choked up at how fast he’s growing. I want to freeze him….. but look so forward to it all. Thanks for a sweet post. I enjoy reading your site…. 🙂

  20. AmberStar says:

    When my youngest started kindergarten I went home and it was so quiet I sat down and cried. It is a big step when they start school…their little world widens a lot.

  21. Lorie says:

    I couldn’t have said it better. I just sent my third one off on Monday. Wow, the time goes by so fast, but each stage allows us closer to see where God will take them!!!

  22. Caroline says:

    2 days from now, Monday, I will be taking my brown eyed boy to kindergarten. I find myself clicking my heels with joy and then crying into my cereal periodically. Your post was beautiful and so helpful right now. Congrats on making it through YOUR first few days of kindergarten.

  23. Shannon says:

    I balled my eyes out when my first son went to kindergarten, seems like yesterday. By the time the next one goes you throw a mini-celebration party for new freedom, lol. Now we are about to enter the middle school phenomenon, I am terrified.

  24. CousinJ says:

    Shannon, I’m glad you posted this again. Ethan starts Kindergarten this Thursday and it has just started really sinking in this week. I know one day your little guy will read this with a big smile on his face:).

  25. Alyson says:

    My middle baby is starting K in 2 weeks, oldest to second grade, youngest to preschool. It’s so bittersweet, it definitely helps to have faith that God IS steering them (although I know there will be some tears from mama on the 2nd of Sept, and I’m not quite sure how I’ll make it through sending my little guy off to K in 2 years).

  26. Tameka says:

    The title caught my eye, as I will be sending my little boy off to Kindergarten next week! I’ve been battling the emotional rollercoaster myself! You words were beautifully written!!! 🙂

  27. Crystal says:

    When I dropeed of my two boys on their first days, I was so tempted to go back and check up on them. As soon as I saw them after I asked them so many questions, I think they thought I was crazy. lol Ah, those are the kinds of days I will always remember as will you.

  28. gerry says:

    I’m typing through tears! This is such a sweet letter. My daughter started kindergarten 23 years ago & I still look back on that first day of school & tears fill my eyes. She was such a good student…coming home each day to let me know “You’re doing that wrong. That’s not the way Mrs. Compton does it.” She was always the teacher’s pet & loved school so much that she’s now a 10-year college student. She just can’t seem to get enough to satisfy her craving for knowledge. She is married & has given me 3 of the most wonderful grandchildren possible! As much as we hate to let go, we have to. But if we’ve done everything we needed to do, they will never actually “leave us!” And we need to be sure to raise them in church so they keep God constantly with them throughout their entire lifetime. Things DO get easier…I promise!

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