On Letting Go


That day has come…

Where I nervously pack his bag…pick which shirt and short to wear…

The day I was swept by mixture of emotions (maybe) only mothers can truly understands. Part of me is proud seeing this boy embark on a new journey, a huge milestone in his life, thrilled to hear about his adventure in that place. Yet, I was swept away with sadness.

Yes, sadness…

It started a day before, when my parents and I took him to get his hair trimmed. Well, it went on beyond it. We pretty much let his curls got chopped off. Those cute precious soft curls that has been on his tiny head for 2 years!

In an instant…my tot loses his ‘babyish’ look, in an instant I miss those annoying curls.

How is it possible for a four years old to suddenly look all grown up? No one ever warned me about this. He’s my baby…my pumpkin! Yet, he’s no longer a baby. Lil’ A is almost too big to be called Little anymore.

So on that morning when we stepped into a new territory where he will be spending times playing, learning, socializing for the next few years…you could almost see my heart dragging behind my steps.

I had kept him to myself for four years…and now I had to peel myself away from him – at least for a few hours. This was even harder than leaving him when I started working full time.

My worry wart Mommy self kicked in when I saw him crying at first because it’s all new and he wanted his Mommy to stay in his classroom.

Maybe he’s not ready!” worry wart Mommy chipped in “Let’s just take him home…” she continues to terrorizing me while the try-to-be-wise-Mommy- in me said “Do NOT hover!!! He’s fine!

Had to fight my tears when I was in the principal’s office,  as she must’ve sensed my nervousness and tried to assured me that Lil’ A will be fine.

It was a pure mixed up emotions all rolled into one.

Letting him go into that classroom is like opening the door and setting him out by himself to discover the world for the very first time.

This Mommy definitely needs to toughen up and be on the sideline like any other good mother and not being a helicopter parent.

How was your kid’s first day of school like? But most importantly, how did you handled it?

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28 thoughts on “On Letting Go

  1. BLOGitse Reply

    The first day is always difficult but after that it will be daily routine.
    For us, adults, first day alone in a new work place or travel is exciting so it’s no wonder if it’s a strange step to children to become individuals in a society…

    • Maureen Post authorReply

      Thank you my friend. He’s used to the idea of school now and it has become a daily routine for us all. 🙂

  2. Kate Reply

    Ok, I’m not going to lie, I got choked up reading this blog post.

    I’m not at the school point yet, but since I have a hard time leaving the kiddo crying when I leave the house, then I’m almost positive I will spend days crying when he goes to school!

    Hope Lil A is having fun! And that mommy is doing okay!

    • Maureen Post authorReply

      Awww…thanks Kate! The first few days was hard for sure but after a week we all had fallen into the new routine but I still miss him while he’s in school. Hugs your way, my girl!

  3. gigi Reply

    hang in there girl, the first day is always the toughest. He’ll do great 🙂

  4. Justine Reply

    I agree that some of these milestones are definitely harder on us moms than our little ones. My girl’s only 2 but she started preschool and I took time off of work in the morning and her dad came too for the ceremonious first-day drop off, thinking we’ll have to deal with her emotions. Except she was thrilled to pieces, said bye and turned away even before we did. I just wasn’t prepared for that! It’s good that she’s exerting her independence, but as a parent, it’s a rather bittersweet feeling. You want to let go, yet you always want to hold on, so I understand your heart completely on your son’s first day of school.

    • Maureen Post authorReply

      Oh Justine, that description is what I thought will happen to us but instead, he clings to me like a poor scared little boy. It was so hard to finally telling myself to trust the teachers enough and left him in his class room while he was busy playing. You described it so sweetly that it is bittersweet. Thank you, Justine!

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  6. MoosMamma Reply

    Oh,,, do I feel your pain…. Last year FP started preschool… it was only twice a day.. for a few hours… but I sooo missed her… but she loved it so I had to be okay with it… then came this year.. kindergarten… which is now a full day of school… it used to be only half day out here… and it was hard… but she was soooo excited… and it was… and is still hard.. some days more than others… but I know she is happy… and learning so much.. now I keep telling myself I will use that time to get the house clean so we can have more quality time when we are together… or go to the gym… one day it’ll happen… 🙂 You’ll get into the routine… and seeing your LO happy… makes it a bit easier 🙂

  7. Jessica Reply

    Oh, this was a beautiful post Maureen. While my little girl has some years to go before she enters school, in reading your words, I was right there with you. I can’t imagine what that day will one day be like. I am getting misty eyed just thinking about it. Hugs. You will get through this, and you both will be stronger for it.

  8. One Girl Ideas Reply

    Oh I remember that day like it was yesterday, even though it was 10 years ago! It was so hard to let my baby go to school, and it still is today. Right now I am counting the days I have let to drop him off at school before he drives next year. Every time he gets out of the truck I watch him cross the street, walk into school and I see that little boy that I left the very first time!

  9. Booyah's Momma Reply

    Well, first… you are a great mom, Maureen, regardless of whether you’re helicoptering, staying on the sidelines, or are anywhere else in between.

    I remember my daughter’s first day of preschool. She cried. I cried more. But now she loves it, and she’s learning so much. And I only cry at drop-off sometimes now. It will get better, I promise.

  10. Hela Reply

    I identified with you so well…

    My oldest, 5 1/2 year old, is starting “big” school this week. I never put her in pre school or day care (as I was able to work around it and do all that at home…) but now it is time to start KINDY, or the first year of the elementary school, here in Australia.

    I am really happy with the local school and their orientation program, but I am nervous…

    All is ready – the uniform, the bag…. it’s just me not completely prepared for this.
    When did she grow up?

    Thanks for your nice blog. I’ll be coming back…

  11. parenting ad absurdum Reply

    My oldest hasn’t started kindergarten yet (Sept), but I felt this way with both of them the first time I dropped them off at preschool – and pretty much every day since!! It’s so hard – even though the teachers swear up and down they’re totally fine after I leave…my poor heart!

    Thanks for your note on my gp at belle and bean!


  12. Unplanned Cooking Reply

    So sweet! Letting go is so hard. And for me it happens every year, letting go for preschool, for kindergarten – next up, first grade. It’s so sweet to watch them grow, and I try to remind myself that one of the most important life skills is to learn how to fail. Because that’s how you learn to pick yourself back up. So even when he is struggling, I tell myself he is also learning to be resilient. (And then I tear up and take him home :).

  13. Nami Reply

    Y’know – it NEVER gets easier. Especially when they start TELLING you to go and you’re not ready. Very embarrassing…

  14. Jill Reply

    Oh, Maureen! It is such a bittersweet moment when you walk out that door.

    No matter where he goes, or who you leave him with you are always his momma and he will always be your boy. Even when he stands 6’0″ to you.

    The first day I left Jonesie it felt like my heart was ripped out of my chest because he was having fun with the other kids. In the end, it was best for him.

    I hope it has gotten easier for you.

  15. vanita Reply

    that first day is hard, and i’ve done it twice and have two more times to go. even recently, when the oldest started high school, taking the trains herself, being more independent, even that’s hard. if i could, i’d take her to school everyday and pick her up everyday. letting go always seem impossible, but it’s for the best, right?

  16. Sammy Sue Reply

    How heart-wrenching! My Little Big Guy is only one and already I dread him leaving me like that! I remember when he was just a few days old and I laid him down for a few minutes…the first time he didn’t cry…and I thought to myself, “This is the beginning of him letting go, of his independence, of him not needing me!” I know, crazy, but I couldn’t help it 🙂 What a beautiful, honest rendering of your Baby’s first day of school. Thanks for sharing!

  17. Fadra Reply

    I cried when I took my son to a part-time sitter when he was 4 months old. She’s become like a grandmother to him. But he just turned 4 and he’s outgrown the homecare. I know school is coming soon and so does he. Neither of us wants it but we know it’s inevitable. Until then, I’m saving up my tears because I’m pretty sure there will be a flood of them.

  18. Sammy Sue Reply

    I hope you don’t mind…I linked back to this post on one of my recent posts 🙂 Please let me know if you would like me to unlink it.

    Thanks 🙂

  19. Sunithi Reply

    Been there … done that twice. It’s gets easier with the second … and wait till it’s the first sleepover … it’s worse 🙂 and when they get to be 13 like my oldest …. major ” letgo” stress !! Hang in there 🙂 🙂

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