First Day of Preschool + Pinterest Mom Guilt

first day of preschool

Today was a big milestone day: Caleb had his first day of preschool! It was surreal for me since I attended the same program and spent the hour reminding myself that I had not traveled back in time, but was there with my own child instead of being a student myself.

He was so excited to go to “Tollgate School” that I could only persuade him for one quick photo before he scampered inside.


I promise he picked that shirt himself. Some of you may realize the humor in his genetically programmed love of a good blue button down; Keith would have been so proud.

Today’s session was a shortened session and parents were encouraged to stay as the kids had an hour of free play. Caleb was happy to see one of his little friends there and worked hard to “color” a picture of me with a glue stick. He loved the sand table, play dough, and the “other trains” (a duplo train set).

When he saw his little mailbox with his little creations, his face lit up. It’s such a joy to see him growing up and thriving. I can’t wait to see how he blossoms in this new environment.

After school, we went for a first day donut (because everything should be celebrated with donuts). Caleb picked chocolate frosted with rainbow sprinkles, ate the top off, and then let me finish it (one of my favorite parenting perks). From the moment of his first bite, he was a chatterbox about his first day’s experience. Note to self: when you want to hear what’s on his mind, buy him donuts.

Today was also significant for another reason. It was bittersweet to bring Caleb to his first day without his daddy. My heart strings were tugged so hard when I realized how much he has grown up since Keith died. One sweet mom came over and commented on how hard it will be to drop the kiddos off and how she will cry, too. Explaining to a stranger why a bittersweet milestone is made more difficult because I’m a widow takes a bit of the magic out of a special day. To her credit, she was wonderfully empathetic and so kind. I will thank her one day for that.

Enter the “mom guilt”. As my friends’ kids are going to school, they’re posting photos of their kids with adorable signs or other sentimental props. I had one of Keith’s ties in my bag to use, but I couldn’t bring myself to use it. In our case, Pinterest worthy sentimentality makes a day more bitter and less sweet. I start to feel guilty that I’ll regret not documenting these moments and that my inability to plan ahead and execute fun ideas will be a disappointment to my kids down the road. Maybe I will regret that. Maybe Caleb will wish he wore his Dad’s tie on the first day of preschool.

And then I manage to capture photos like these. These are the moments when the mom guilt washes away. It’s okay to downplay the huge milestones. It’s okay to let a whole day go by without a brilliant parenting moment. It’s okay to not feel like super mom. It’s okay to not be perfect or ideal or whatever impossible standard you’re failing to live up to.

When I see these pictures, I know that we are doing more than okay. These smiles tell me that I am doing enough. I hope that if you’ve struggled with the beast our culture has accurately named “mom guilt,” you can see in your children’s smiles that they are loved and you are enough, too.

And maybe I’ll make Caleb wear the same outfit again next week and have a first day of school do over; he’ll never know.

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  1. Darcie? on September 8, 2015 at 8:25 pm

    Donuts after a first day make for a great tradition…whatever you do will be unique to you, and will matter deeply to Caleb and Libby…I always made brownies for the first day of school, then it did the first day of college(mailed them)…then the first day new job…now Sarah continues the tradition with her girls, and they, too, look forward to it… I have no doubt that your children will have wonderful memories of their childhoods.

  2. Kim Stirtan on September 9, 2015 at 5:08 pm

    Loved reading about his first day and seeing the pictures of Caleb and Libby 🙂
    And you sharing your real emotions of it all.
    Love you,

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