On His First Day of Kindergarten, I Can’t Help It

To my son,

I’ve been secretly dreading the day you would leave my side to start school.

A lot has happened since you’ve been born (losses, moves and everything in between!), but after making the decision more than 5 years ago to leave my corporate job and work from home, this is one of our biggest transitions yet.

I’ve quietly prepared myself for today, knowing very well I would be a damn basket case.

But what’s more important is that we’ve prepared you for today.

We’ve spent a lot of time talking about what’s happened in your life so far and making sure you were ready for your first day of school.

We’ve talked about being kind and standing up for yourself. We’ve talked about sharing and waiting your turn and listening to the teacher. We’ve talked about homework and the things you’re excited to learn. We’ve had to teach you about loss at too young of an age, but you know grandma is with you in spirit. We’ve talked about stranger danger, good-touch-bad-touch, safety and tried to be as realistic with you as you can understand. We talked about bullies and how to ask for help. We’ve talked about not trading your lunch and where you’ll wait for me to pick you up.

When it comes to 5 year old life, we’ve covered it all.

Today came fast. I walked you and your shiny new dinosaur backpack up to your school. I smiled and admired your fresh haircut and new gym shoes. The green and blue shoes you had to have.

As I held back tears and watched you get in line, I can’t help but be proud of the human you’ve become.

Then you turned, waved and took a piece of my heart with you.

Even though I longed to steal one more hug from you, I waved back, said “bye baby” under my breath as I watched you go.

Because despite it being bittersweet and despite my sadness, I would never stop you from spreading your wings. It’s time for you to put everything you’ve learned to the test.

Now I sit here, sipping tea in quiet. There’s no one here to ask me a billion questions, tell me they’re still hungry or hold my hand when I leave the house.

I shake my head at how fast these past 5 years have gone. When you were born, your grandma warned me not to blink.

I guess I did. (Sorry mom.)

As I wonder where time went, I can’t help but think about how you’re doing.

Are you making friends? Did you remember to ask where the bathroom is? (Please don’t try to hold it all day!) Will you eat your lunch or be too excited about recess? Are you being your usual animated, social self or are you uncertain about your new surroundings? Will you be embarrassed if you accidentally call the teacher mom?

Deep down, I know I’ve done my best. We always do. With whatever we have and whatever we know, parents do their best.

But through my tears and all the emotions, I can’t help but wonder…

Did I read to you enough? Play with you enough? Teach you enough?

Did I say “hold on a sec, I’ll be right there” too many times?

Did I kiss and hug and tell you “I love you” enough so that you’re sure I didn’t just drop you off and forget about you?

Are you still worried there will be a school bully or did we instill enough confidence in you that you’ll get help if you need it?

Are you using your innate problem-solving skills to figure out what you need to figure out today?

Do you know I miss you and can’t wait to hear how your first day went? (I hope so!)

I can’t help but wonder.

I can’t help but worry.

I’m your mom. I can’t help it.

I also can’t help but smile when I think about how much fun you’re probably having.

It’s what parents do. We can’t help it.

I know we did our best. For the past 5 1/2 years, we’ve prepared you for today. This is the day you’re putting it all to the test.

And I know you’ll be fine.

You always are.

You’ll figure it out.

You always do.

And I can’t help but smile as I drink my tea and feel so incredibly proud of you.

Love, Mom.


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