In 1996 the advertising department at Staples had a genius idea, worthy of Sterling Cooper’s Don Draper himself. The soundtrack for their back-to-school commercial featured the opening line from a classic Christmas carol, “It’s the most wonderful time of the year.” The concept was clever, but the execution was pure gold because it captured the sentiment of parents and children alike. The scene was unforgettable: a dad joyfully gliding up and down the aisles with his shopping cart, gleefully tossing in supplies, while his two kids with their shoulders slumped trudged behind him looking utterly unimpressed. Parents immediately connected to the excitement the father felt because he couldn’t wait for some semblance of normal to return once the kids were back at school… while kids recognized the impending doom of the fast approaching school year.
For those who don’t remember the 90s (or weren’t alive yet), here’s a little context… Unlike today, when holiday promotions seem to creep up earlier and earlier into the calendar – frequently before the previous holiday has ended – the thought of hearing or seeing anything Christmas-related in the summer was absolutely unheard of. The only exceptions were the occasional “Christmas in July” celebrations, which at this point were a quirky novelty instead of today’s mainstream marketing strategy. That’s part of what made the ad stand out. It was bold, cheeky and perfectly captured the dichotomy between children and their parents during the back-to-school season.
As a kid I remember groaning out loud whenever that commercial came on the television (and reminder, this was back in the days when you couldn’t just skip ads – PVRs didn’t exist yet. The closest thing to “ad-blocking” was frantically hitting the mute button or sprinting to the kitchen for a snack before the show came back on.) Sure, I loved back-to-school shopping for the stuff – carefully selecting the notebooks I’d use, finding the perfect selection of pens and pencils, selecting a new pencil case to hold them, and sometimes even a new backpack. Plus anticipating the feeling of opening the new notebook for the first time with its clean crisp unbent pages, perfectly sharpened pencils and using a new pen for the first time. But the idea of actually going back to school? Well that was another story entirely.
During my thirteen years of elementary and secondary education, I attended eight different schools, in three different cities. While there were moments of kindness and fun along the way, the negative experiences in the classrooms far out weighed the good ones for much of my youth. The frequent changes in schools were necessary for various reasons, it meant that more often than not, I was the “new kid”, trying to decode the unwritten rules, figure out social hierarchy, and learn the names and faces of a whole new set of classmates. More often than not, it was a slow and isolating process. Fortunately I had the right support in place at home to get me through the rough patches relatively unscathed and by the time I graduated, things had improved. Still, those formative years left a lasting impression. It’s one of the reasons I believe so strongly that we need to acknowledge the emotions our kids may be feeling as the first day of school approaches – especially if previous years have brought more struggles than smiles.
As a parent, I’ve made it a practice to take some time in August to reflect on my children’s past school experiences, who they are as individuals and how they’ve changed over the summer before we start talking about the new school year. This process helps me meet them where they are emotionally – whether that means boosting their excitement, calming fears or addressing challenges head-on before they have the chance of growing into bigger problems.
I’ll admit, this year I’m feeling more cautious than I have in the past. Last year was a tough one for all three of my kids, each for different reasons. I want to stay hopeful, but I also want to go in with my eyes open and my toolkit ready.
Right now, I’m in the midst of my annual back-to-school prep: checking off supply lists, going through closets so that I can replace the outgrown clothing, brainstorming school-safe snacks and lunches with the hopes that they might actually get eaten instead of returning in their original form. I’ve also been stocking the freezer up with crockpot meals for the inevitably chaotic weeknights filled with homework, activities and work deadlines that will come faster than any of us are ready for.
The big change this year is my focus on front loading. I’m working on giving the kids as much information and preparation as possible so we can have a smoother transition from the carefree chaos of summer to the structure (and occasional stress) of school. We’re talking about the fun stuff – seeing friends again, catching up on what everyone has been doing – but also about how things might be different. Friendships change over the summer, especially when kids grow and mature at different rates. Dynamics shift. The way things were last year won’t necessarily be how they are this year, and that’s okay.
The first few days of school are often frustrating while schedules, seating charts and class lists get sorted out, but they also offer a soft entry back into the structured school year. There’s a chance to reconnect with last year’s teacher and classmates before diving into academics headfirst. That little bit of breathing room can make a big difference in easing into the new routines.
I’m also being intentional about revisiting some of the bumpier parts of last year with the kids. We’ve been talking openly about friendships – trying to identify the ones they want to keep, the ones they want to explore, and the ones that may be better left in the past. We’re discussing how to respond to unkind behaviour and bullying in ways that keep the confidence intact. Plus we’re brainstorming strategies for when they feel overwhelmed in class, whether that’s asking for help, taking a quiet moment or finding a positive way to self-regulate.
Back-to-school season may never feel like “the most wonderful time of the year” for everyone in the family – but with preparation, honest conversations and a little empathy, we can help our kids head into the new school year with a little more confidence, resilience, and hope.