The day finally arrived to take my first child shopping for school supplies, but nothing turned out the way I'd planned. In short, chaos ensued.

Shopping for school supplies
Credit: George Rudy/Shutterstock

It was 2008, and I had looked forward to this moment for a long time: My first child was starting kindergarten. I lovingly picked out a backpack/lunchbox set at Baby Gap and got it monogrammed with her first name. I hung new school clothes in their own section of her closet. I bought Mary Janes and white knee socks to go with plaid skirts and sweater vests. I had a certain picture in my head of how a little schoolgirl should look. It was all very idealized, though; I had been homeschooled from kindergarten through 12th grade and had never been a part of this before.

What I Thought Would Happen

My vision included how my daughter and I would buy her school supplies together. We would consult the list, wander the aisles, find all the items in her favorite colors, and go out to lunch afterward, all while laughing and having fun. We would then go home, admire the sharpness of the new crayons, smell the waxy scent, mark all her new supplies with her initials, and place them carefully in her new pink plastic school box.

pile of school supplies

What Actually Happened

We went to Wal-Mart, which was a normal experience until we hit the back-to-school aisles. Wide-eyed parents clutched crumpled supply lists in their hands, begged children to let them think for just one moment, and threw back Starbucks cups like tequila shots. School supplies littered the floor; grumpy and harassed looking employees darted between carts to retrieve and replace them. It was not idyllic by any means. I struggled to keep my daughter from getting stepped on, and the din woke my infant. And, after all that, I was only able to get some of the supplies there.

Unbeknownst to me, school supply lists can be very specific. This one specified that Prang watercolor sets were a must, because "the pigments are superior" and no other kind would be good enough for the kindergarten art projects the teacher had planned. The eraser must be white (why, God, why?!), but Wal-Mart only had pink. I was seized with fury at realizing that the required Crayola 24 pack cost more than the Crayola 64 pack, but my hands were tied. I threw the 24 pack in the cart, muttering my displeasure. A woman nearby nodded at me in solidarity. Her hair stood on end as if she'd actually begun yanking on it with stress.

The insanity continued as we moved on to the other items on the list. I could not find manila paper in the correct size. Did the requested size of tissue box actually exist? Did the number of hand sanitizer ounces really matter or could I buy this bottle that was bigger and yet cheaper? Meekly, I added things to my cart only if they were precisely what was requested. I decided to buy what I could and move on to Target. I was sure I'd be able to finish my list there and move on to our delightful lunch.

Target was just a slightly more expensive version of the same chaos, and after I scoured the aisles I still had a few things missing from the now-hated list. This had stopped being fun a long time ago. The baby needed to nurse and my soon-to-be-kindergartner stared wide-eyed at the adults pushing, yelling at their kids, and groaning aloud. We checked out and reassessed the situation in the car as I nursed the baby. I decided to try Staples, and vowed that whatever could not be bought there would be substituted with the closest thing to it.

Staples yielded the white eraser (although I was forced to buy a pack of five erasers to get it), and the last Prang watercolor set. I raised it above my head in victory. I had to compromise on the size of manila paper and tissue boxes. All in all, I spent twice as much and two hours longer than I expected on back-to-school shopping. We had to cancel our special lunch because we were all exhausted. Instead, we went home and watched Dora the Explorer while eating sandwiches.

Growing Pains

I participated in this madness again, every August. May of 2011 brought a new innovation: The school offered to charge an exorbitant price to order school supplies for me. The flyer came home in my daughter's backpack on a bad day. I'd been doing the budget and hadn't been happy with the numbers. I refused to pay that much for the privilege of not collecting the supplies myself. My next daughter was starting kindergarten so I'd be buying for two, and the price seemed at least $30 or $40 more than I'd pay. I let the order-by date slide by.

Three months later, I wanted to beat myself up as I perused the aisles in despair. I was now dragging four children with me to do this task, and nothing had gotten easier. Even worse, when I did my reckoning by calculator after my purchases, I had spent only $10 less than the price the school had charged; $5 if you count the chocolate bars I bought to medicate myself and my children after the task.

Sold Out & Loving It

Every year since, I've happily forked over a small fortune for the school supplies of first two, then three, and now four children. I don't know if it's actually a fundraiser for the school or not, but I like to think it is. I just visit the website, put in the school number, and click the right grade boxes. It's beautiful, I'm telling you. On the first day of school, I'm not lugging bags and bags of crap. I waltz in, take the first-day-of-school pics with each teacher and kid, and leave. Sometimes I glance reverently at their desks first, where waits a neatly plastic-wrapped package of supplies I didn't have to suffer for. This can be you too, dear parent. Simply hold your breath and write the check in April or May. It's worth it.