I never expected the little boy and his mom deciding on a lunchbox to transport me back in time. But he was a towhead just like my son Jackson at that age and the mom was a redhead just like me at that age, which is to say he was 6 or 7 and she was me 20, 25 years ago.

It happened in Target, while cruising the aisles, when I wandered past the back-to-school section. It was bustling with parents and kids choosing folders, surveying markers and tossing packs of glue sticks into shopping carts. The scene made me smile, though it left a lingering ache.

I used to love back-to-school shopping with my kids. Even though I knew this annual pilgrimage would wind up costing me — literally and figuratively — it was one of those time-honored traditions that marked the end of the summer break and reminded me my kids were growing up (not that I really needed reminding). Every August, we’d set out together for new pencils, erasers and notebooks, the latter of which once triggered panic when we got home and realized we had mistakenly bought college-ruled instead of wide. 

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These days, I hear parents can pre-order their kids’ school supplies and have the whole bundle magically appear in the classroom before the first day. It’s efficient, sure, but where’s the fun — and drama — in that? Where’s the debate over whether Michael Jordan basketball folders are essential to academic achievement? Where’s the hunt for the neon water bottle that must coordinate with the backpack? Some things, it turns out, can’t be Amazon Primed.

Now, with grown kids, the school supply aisle is a thing of the past. No itemized lists are posted on the fridge. The Sharpies at home are hardly ever used. A hole-puncher sits dormant in the office desk drawer. But I still feel that back-to-school tug — and I realize it’s not just about my kids, it’s also about me.

Because the truth is, long before I was a mom in the supply aisle, I was a kid who loved it, too.

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I can still remember school-supply shopping with my mom, the two of us making a day (or part of a day) out of it. The best was when we’d end up at Hamburger Choo Choo, where model train cars on tracks delivered meals to the tables. I couldn’t wait to get home and unpack my riches — fresh, unsharpened No. 2 pencils; pristine, unblemished looseleaf paper; a sliding pencil case with compartments for a ruler, erasers and mini-sharpener; and the pièce de résistance: a brand-new box of 64-count Crayola crayons.

Growing up in New York when I did, school always started after Labor Day, and the Jewish holidays often followed soon after. When the timing lined up, my mom would make it a “double-header”— along with shopping for school supplies, we’d go looking for a new Rosh Hashanah outfit for me. Mom favored dresses that were too little girly for my taste while I always hoped for something that made me look more grown-up. Regardless, there were usually new dress shoes. It didn’t feel like the Jewish New Year unless I was stepping into synagogue in shiny new patent leathers.

I still feel that intersection — between back-to-school and the High Holidays — deep in my bones. Even now, without a child to outfit or a list to check, the season still stirs the sense of a reset in me. 

In Judaism, the month of Elul marks our lead-up to Rosh Hashanah and Yom Kippur — a time for introspection, repentance and spiritual renewal. We pause to remember what we’ve done and what we will do better, who we might have wronged and how we can make it right. It’s a different kind of “back-to-school” moment — one that doesn’t involve three-ring binders but still asks us to take stock and get ready.

There’s a name for this process: cheshbon hanefesh — an accounting of the soul (thank you, Rabbi Randy). Like those checklists I once carried through store aisles, it asks: What do I have? What do I need? What’s still missing?

These days, my lists live more in my head than on paper. But the instinct to mark a new beginning remains. I feel the same pull to show up ready, to gather the right tools, to honor the power of a fresh start. 

I didn’t buy anything at Target that day. I didn’t need to. But I left with a gentle reminder that the new year still calls us to prepare — to come as we are, but maybe a little more organized, a little more intentional, perhaps even a little more hopeful — and if we’re lucky, in a pair of shiny new shoes.