Lessons Learned from a Chronic Over-packer with a Questionable Attention Span

Packing for a trip feels like a high-stakes game where I either win by bringing everything I could ever need or lose by forgetting something that feels critical the second I realize it’s missing. My luggage is stuffed, my lists are endless, and yet somehow, I still manage to forget the essentials on a near-perfect schedule. Here are a few hard-earned lessons from someone who packs like they’re moving in but often forgets to bring their toothbrush. Here are some tips and some of my favorite products I use for travel. *Please note some of these are affiliate links.

Lesson 1- Roll your Clothes and Plan Smart

My packing used to look like I’d tossed my entire wardrobe into a couple suitcases, but I’ve now evolved...slightly. For most trips, I can pack for a week in nothing more than a carry-on and overnight bag. Rolling clothes instead of folding them saves space, and I’ve found that it keeps my clothes looking way less wrinkled. Another game-changer? Planning for two tops per pair of pants. This mix-and-match strategy keeps me covered (literally) without needing a full change between daytime & evening.

Bonus lesson learned here If i am flying and need to check a bag I always pack a toothbrush, toothpaste and a change of clothes in my carryon / personal item. Its been a lifesaver to be able to freshen up after a long flight or worse, delayed luggage arrival.

Lesson 2- Bulky Jackets

I’m usually cold. So early on, I used to pack 2-3 jackets or blazers that matched my outfits. Even in the summer. I wanted to make sure if I was going to be in an office building, conference room, restaurant, movie theater, etc that I was prepared. In the fall and winter, in addition to my actual coat, just in case the temperature fluctuated by a whole degree or two I would also pack or wear  something with a little more weight, you know. Just in case. But I’ve since learned: one versatile jacket is the way to go. A lightweight blazer or neutral-colored jacket that pairs with all my outfits makes more sense. It’s practical, looks great, and saves me from the shame of stuffing a second jacket in my already bursting suitcase. If I am traveling in the winter and will be doing a lot of outdoor activities I typically bring a heavy vs. the single lightweight jacket.

Lesson 3- The packing Cubes

Packing cubes are the unsung heroes of organized travel. Not only do they help divide your clothes (because who wants to dig through a suitcase every time they need socks?), they also make unpacking a breeze. I’m less likely to forget something because I can see everything I packed.  Here’s a fun side effect: every cube has a purpose, so I’m less likely to panic-unpack and lose things mid-trip.

Lesson 4- The Mini Medicine Kit

When I visit an area I am unfamiliar with or when I am pressed for time, realizing I need a Band-Aid and have nothing to stop the blister I can feel forming on the back of my heel is one of the worst feelings. Now, I pack a little first aid kit with the essentials—Advil, Tylenol, Band-Aids, blister relief, Benadryl, and travel-size tissues. This little bag has saved me (and sometimes even my travel companions) more times than I’d like to admit. I keep it stocked and in my carry-on or purse always. This one from amazon is a great starting point. You can always swap out and update to your specific needs.

Lesson 5- My Charger Bag

All my chargers now go into one bag, which I’ve decided is a necessity rather than an “I’ll remember” situation. I got this one on amazon but I have also used the other cosmetic bag sized bags. Chargers for my phone, AirPods, watch, laptop—they all have a cozy spot in this one magical bag. Now, I did learn the hard way to take it one step further than just trying to wrap the cords around themselves, throw them all into one bag and hope they stay wrapped. I now use these silicon cord ties at home and on the go. They keep everything tightly together so I can quickly see if this is my lightning cable or  my USB-C. My charger bag is always tucked safely in my carry-on, and life is better for it.

Final Thoughts-

The more I travel, the more I realize that perfect packing is like a mythical unicorn—beautiful, elusive, and probably imaginary. I still overpack, but now I’m just more strategic about it! So, here’s to rolling clothes, packing cubes, and not totally forgetting things this time around. Happy travels!

*Amazon Affiliate links included in blog post.