“You know they’ll have that there, right?” my boyfriend Jack asks while I stuff body wash into my bulging bag. What self-respecting Airbnb doesn’t have soap in their shower? I, however, am particular about my lavender-scented soap. I must have my own toiletries, which isn’t so outrageous, but the problems arise when I push my luck with the amount of books I take along for an overnight.
So when I brought two 500-page books but forgot my toothbrush, I knew I had a problem. The art of simultaneously overpacking and underpacking is one that I have mastered. I am a bona fide packing disaster.
Those 500-page books? They never saw the light of day. And I, of course, ran out of socks by day two.
We were spending a week in a cabin with plenty of activities and places to explore. But, of course, I had to bring my heaviest, hardest-to-read books and a month’s worth of crossword puzzles just in case.
Just in case: the three most dangerous words for the packing-challenged. “I’ll bring my bathing suit, just in case”—it was the middle of winter. “I’ll pack business casual, just in case”—we were hiking in the mountains. “Fourteen pairs of underwear, just in case”—in case I suddenly become incontinent. On top of it all, I am notorious for forgetting something crucial—my contacts, toothpaste, pajamas, my phone, or anything in between. But, thank goodness I have my trusty blazer and slacks just in case we stumble into a business casual event on the Appalachian Trail.
On one occasion, I was determined to shed my reputation as an over-packer on a weekend trip with Jack to visit his grandparents. The kicker was that my parents were coming along too. So it was about a 9 on a scale that measures Significant Weekends. I made lists upon lists upon lists. They were color-coded, with categories and columns and checkmarks and subheads. It was my masterpiece. I pictured my skin care routine, smelling delicious after the fragrant shower I’d take, my sensible one book to read before bed, what I’d wear on our outings, and the comfortable outfit I’d assembled for the ride back. I carefully folded and tucked, and packed everything I needed.
And I did it. I beat the curse.
One teensy snag: I forgot the bag.
All I had was my useless purse—yes, I’m also not good at purses. Mine would win me a fortune on Let’s Make a Deal. I still carry a bottle of Nyquil from when I was sick three months ago and Canadian coins that, for the life of me, I can’t quite figure out how I came to acquire. So on this occasion, I turned to my parents, who are always prepared, and humbly nabbed the extra pajamas and clothes they packed.
I didn’t inherit the readiness gene from them. My dad can pack a week’s worth of clothes into a fanny pack and still bring towels to a hotel, just in case. My mom, though still an expert packer, is the opposite: when she comes to visit, my neighbors think I’m getting a roommate.
So while my parents are successful packers, albeit on opposite ends of the spectrum, I’ve come to realize that the packing odds are just simply not in my favor.
But believe it or not, I actually love it—the art of packing. There’s a bit of magic in watching outfits stack up as trip anticipation builds. As I reflect on trips I’ve taken, I remember the mouthwatering restaurants, the heart-racing adventures, and all the memories that will last me a lifetime—not how uncomfortable it was brushing my teeth with my finger.
Featured illustration by Heedayah Lockman. This article originally appeared in the June 2025 issue.
