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Sonoma Family Life Magazine

When Will the Trips to Target End?

By Jessica Guerrieri

As a former educator, self-appointed humorist, and mother of three, I’m here to guide you through what’s to come. Though I’m only slightly more qualified to offer unsolicited back-to-school advice than the supermarket octogenarian who waxes on about the benefits of fresh beet salads.

The two most common rookie mistakes: 1) Buying back-to-school supplies without the teacher’s list in hand and 2) attempting to gauge how anything is going before one month and one week into the school year.

The first week is a mythical, illogical unicorn. It’s mostly reconnecting with friends, fun class summer surveys, and breaking in new shoes. Do yourself a favor: Save your receipts and don’t humble-brag post about how amazing everything is. You’re going to feel really sheepish when your kid sets the school record for volume of glue eaten.

The second week is quite possibly the most unpredictable. It could all go completely sideways, but fear not, this is normal! The greatest thing you can do as a parent is continue to establish a routine that’s sustainable for the long haul. Meaning, don’t surprise the kids with sugary treats unless you want “Friday Donuts!” to become a weekly standing tradition. And go ahead and throw away your elaborate, well-intentioned reward chart made with the same gung-ho enthusiasm of the first week of lockdown—you cannot possibly keep on top of that.

During week three, your little ones officially realize that their 3–6 hour, 5-days-a-week experience is, in fact, school and not a trip to Disneyland. This week may involve some light to moderate bribery. I hope your children are still thrilled by stickers. 

As a former study skills teacher, I suggest sitting down with your students and going through their backpacks. Crumpled papers and brown bananas, at this point, don’t necessarily doom them to star in a future episode of Hoarders. But make sure they are the ones to clean out the pack, and then add “backpack check” to your floor-length daily checklist. 

One month in and, sadly, you aren’t quite inside the window of time that I consider to be cruise control. You’re still frequenting Target to purchase shoes that don’t cause blisters and a backpack that’s seven times bigger than the original (to carry the flood of paperwork sent home), and to return any clothing items you purchased thinking “this is so cute” only to find out your fiercely independent pre-pre-teen strongly disagrees. 

Congratulations! You made it to my arguably completely arbitrary “one month and one week” milestone. Good, bad, and definitely at times ugly, the new reality finally has settled in. I never promised perfection, just a somewhat blurry version of normalcy, one where your children may be the students, but every day you still feel like the one getting schooled. 

Jessica Guerrieri is a mom and a freelance writer and aspiring novelist. Find her at and on Instagram and Twitter @witandspitup.