I Was the Mom Who Never Looked Back at Drop-Off—and I Have Regrets

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One blissful August day seven years ago, I drove my eldest son to his first day of school. He walked right in the door, excited. He didn’t even glance back in my direction, and honestly, I was grateful for that. I was just as enthusiastic as he was, and I felt proud to have a kid who had enough confidence and self-assurance not to need me to hold his hand through the whole process. At the time, it felt liberating and even boosted my mom-ego a bit. My kid is so chill he doesn’t even cry at drop-off! I told myself.

I was never the mom who cried at the thought of her baby being away for the day at preschool. I didn’t choke up on the first day of kindergarten because my baby was “growing up.” Instead, I was the mom who embraced the freedom and glorious change in our everyday schedules. I also welcomed their chance to be independent little beings who didn’t rely on me to make every decision, every meal, or deliver every snack. As years passed and my next two kids entered school, this remained true. Drop-off was breezy (for me). I rushed out the door gleefully, ready to attack all the things, now that I had one (or two or three) fewer little monkeys crawling up my leg, watching me pee, or making a huge mess just as I was about to tackle a task. 

Looking back, I do still appreciate that I was the mom who never cried. I genuinely think it allowed my kids a sense of autonomy and confidence. Walking into a new place with so many kids and adults they had never met or even seen before can be scary! So never having to be the mom that stood outside the door listening to their child cry through the first week of school seemed a blessing. 

I never thought the day would come when all of those seamless drop-offs where I joyously skipped to my car and ventured off into my day alone—and the tear-free preschool graduation ceremonies—would fill me with sadness and regret. I feel slighted. Now as my eldest is about to graduate elementary school, I feel like I missed out on having that connection or that “moment” when my kids needed and wanted me.

Fifth-grade graduation seemed so trivial to me as a kid. A non-important “milestone” that was more for my parents than for me. And honestly, I get it now. It is for the parents. Because as soon as our kids go off into middle school, everything about them will change. Their bodies, voices, attitudes… and a connection to us may or may not get lost in the mix. That uncertain, scary feeling our kids experienced going to school for the first time is the exact same fear we have as parents when our kids are inching closer and closer to actual independence. 

So as much as I would like to say I have no regrets about being that mom who, at one time, never looked back, I’d be lying. I have a few. The main one is that I can’t get that time back no matter how I may try. That’s why this year, you won’t see the “cool” mom collected on the sidelines, watching all of the other moms cry and wondering why they are so upset—because it’s not just another day or another year of school.

It’s a moment that needs to be celebrated. That needs to be felt. Because these moments we get as parents are so rare, and before we know it, poof, they’re gone. No, this year I’ll be with the rest of the moms bawling their eyes out. Clapping and hollering and embarrassing the hell out of my kid so that he knows I am there—the whole time. That I am watching. And that he has made me so damn proud.

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