A Kindergarten Drop-Off Survival Guide: No-Cry Tips From an Old Mom


Need some kindergarten drop-off survival tips? Well, since I am halfway to being Octomom, I have your back, friends. Barring some sort of divine intervention, this is going to be my fourth and final first-day-of-kindergarten drop off. Excuse me for just one quick second while I sob and grab a stool to get the box of Hostess cupcakes I asked my tall husband to put on the pantry’s top shelf. Ok! Back! Better! Totally ready to tell you all of my secrets so that you, too, can cry in a closet and eat your feelings in private while putting on a brave face for your brand-new elementary schooler.

Before Kindergarten Drop-Off:

  • Let your newly minted big kid pick out their own first-day-of-school outfit. Relish one of the last days you and your kiddo can hang out together without 7.5 hours of school to get in the way. Make sure to let your kid choose their own clothes, and hope they are a tiny bit ridiculous. If your kid looks too cute on the first day, you might be a weepy little mom puddle.
  • Buy a really great backpack and a super durable lunchbox for your kiddo and hope that you don’t have to buy another until they enter junior high. Keep these purchases super practical—this is no time for sentimentality! 
  • Instead of braving the Target crowds beating other moms out your way to find the last purple plastic folder on your kid’s super specific school supply list, call the school to see if they are selling ready-made school supply kits. If your school doesn’t sell these kits, think about spearheading the fundraiser yourself for next year, and start calling companies for quotes in, like, October.
  • Decide what cute first-day-of-school picture you want to take of your kid and assemble the goods. I like to have them write their deets on a chalkboard and stand on the front porch because I am lazy and this is my last kid and the first 2 started school BP (before Pinterest), so I am sort of locked in for the little 2. But you, my millennial friend! THE WORLD IS YOUR NAVEL-GAZING OYSTER. Stage some amazing pics and share the heck out of them.
  • Pick out your first-day-pf-school outfit. Maybe think about putting a sports bra under that PJ top or pulling on the good yoga pants. You know, something fancy.
  • If you work outside the house, think about taking a half day so you can follow the bus to school like the stalker you know you want to be and take more pictures in front of the sign and helicopter through your kid’s new cafeteria. Don’t fight the feeling.

On the Big Day

  1. Make your kiddo their favorite breakfast, but don’t OD on sugar because these little tiny people have to hold themselves together for a LONG TIME at school. Think protein! I always channel any angst I have about separating from MAH BAYBEEZ into making something huge and time consuming and wearing an apron.  Don’t ask.
  2. Pack an excellent lunch with a sappy note that your kid can’t even read because kindergarteners are illiterate. The note is for you and also for the teacher to know you are the best mom ever. 
  3. Plan a killer afternoon snack and live your Leave it to Beaver fantasy life. I always do milk and cookies.
  4. Be gentle with your 5 year-old, who is experiencing some big feelings. Lower your expectations for good behavior before school, and leave plenty of time to take your super important picture.
  5. Be gentle with yourself and your own big feelings. Maybe think about the waterproof mascara, you know?
  6. Know that as a grown-up, making new friends is hard because there just aren’t as many opportunities to do it. THIS IS ONE OF THOSE OPPORTUNITIES! Be your friendliest, most welcoming, most approachable self at drop-off. Smiles all around. Start conversations with anyone you see. Repeat this at pick up and the next day at drop off, and you get where I am going here. Kindergarten mom friends are ripe for the picking!

After You Drop-Off Your New Kindergartener

Coming home to an empty house after your first kindergarten drop-off and thinking about your itty bitty who is now a tiny cog in the public education machine can give you the sadz. This is exactly why I host a little champagne party for all the moms in my neighborhood on the first day of school. We toast the freedom of the school year, quell each other’s fears, and make fun of each other’s tears. It’s an easy event to throw together: champagne, orange juice, coffee, and my mom’s pull-apart cinnamon rolls. Voila!

pull apart rolls 1 pill apart rolls 2

Cheers to your big day! I hope these tips are helpful. And I’d love to hear your own strategies for first-day-of-kindergarten drop off success!

Sarah Jedd has a Ph.D. in communication arts from the University of Wisconsin-Madison where she teaches and studies the rhetoric of Planned Parenthood. Sarah has 5 (F I V E) children: teens Harry and Jack, elementary schoolers Cooper and Dorothy, and sweet baby Minnie, born in August 2020. Sarah blogs about being a mom of many at harrytimes.com and overshares on IG as @sarahjedd. Sarah, her husband, and their kids live in Verona with the world's laziest dog.


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