Shoulda Woulda Coulda: Learning to Compartmentalize

Compartmentalizing. We discussed it a lot here on the site, particularly in our 30 Days to Packing a Better Bag series, but for some reason, it took me the longest time to put this one into practice. I have typically subscribed to the “black hole” method, by which you jam everything in your bag and dump it all out again when you arrive at a destination. After countless sessions of exploding my bag’s contents all over the floors of dorm rooms across the globe, my sister told me there was a better way.

The first mistake I made was filling my compression sack to the brim. While compression sacks are great for shrinking the size of your clothing, they shouldn’t be abused. When you fill it to capacity, it makes it harder to pack around it in your backpack or suitcase. Rather than having an overstuffed compression sack with little room for anything else, you can leave your compression sack ¾ full so that it will be easier to fit into your bag.

Whether you prefer packing cubes, compression sacks, zippered bags or basic ziploc bags, it’s important to have some sort of system. I used one compression sack for clothes, three cubes for toiletries and accessories and three Baggu zippered bags for shoes, swimwear and undergarments. Everything was placed into a different colored bag and every item had a place. This makes things easier when you’re panicking, wondering what happened to your rain jacket. If you make sure everything ends up back in its original place, you’ll find it easier to repack on the road.

Compartmentalizing also helps when you’re constantly on the road, as you don’t have to unpack compartments if you don’t need them. For example, I left my bag containing swimsuits at the bottom of my bag when I was visiting landlocked Siem Reap and stashed my minimal makeup kit for the majority of the trip. This system works for both suitcases and backpacks, as you fit the bags and cubes together like a puzzle, rather than haphazardly squishing clothing, shoes and everything else together.

While it took me entirely too long to learn my lesson, I’m glad to have developed the right system for me when it comes to packing, unpacking and repacking on the road. I will no longer overpack my compression sack to the point where it’s a large lumpy mass and will instead remember to have lots of smaller bags rather than one large one.