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Shoulda Woulda Coulda: Learning to Compartmentalize

black hole method vs compartmentalizing

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.

Osprey Backpacks

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.

Written by Caroline

Caroline Eubanks is a native of Atlanta, Georgia, but has also called Charleston, South Carolina and Sydney, Australia home. After college graduation and a series of useless part-time jobs, she went to Australia for a working holiday. In that time, she worked as a bartender, bungee jumped, scuba dived, pet kangaroos, held koalas and drank hundreds of cups of tea. You can find Caroline at Caroline in the City.

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Gear We Use

speakeasy hidden pocket travel scarf ad
Speakeasy Hidden Pocket Scarves


Splice Jaisalmer Reversible Tunic
Splice Reversible Jaisalmer Tunic


Eagle Creek Compression Packing Cubes
Eagle Creek Compression Packing Cubes


tom bihn 3d organizer toiletry bag
Tom Bihn 3D Organizer Cube


Sea to Summit Ultra-Sil Daypack - Fits in the palm of your hand!
Sea to Summit Ultra-Sil Daypack


Turkish Travel Towels


Travel Resources

HPL Learnables

Handbag Packing Masterclass – Learn to pack your lightest bag ever in this revolutionary packing class run by HPL founder, Brooke.

Creative Ways to Minimize Your Toiletry & Beauty Kit – Practical tips alongside DIY recipes designed to help you pack lighter, smaller & with fewer liquids. (Also included as a bonus to Handbag Packing Masterclass.)

Book Your Trip

Viator – Enhance your trip experience by booking from thousands of tours across the globe. – Search for hotels, hostels, and apartments using this one resource. Use it for flights, car rentals, and airport taxis as well.

Trusted Housesitters – Save money on travel accommodation by becoming a housesitter. Housesitters often have extra duties, like caring for pets and gardens.

Reader Interactions


  1. Jaye says

    One caution in regards to compression sacks – more space means you can get more into your bag so be aware of the weight you’ll have to carry and/or pay for.

  2. Julia says

    I use freezer size ziplock bags for packing. Not only do they help me fit everything into my 40L pack but they help me stay organized on the road so when I’m rushing out to an early morning flight and I need a different t-shirt I know which bag it will be in and where exactly in my bag to find it!
    Also, a supreme benefit of a 40L pack is I know that even if I pack to the brim (and I do…) it will still be underweight!

    • Chrissie says

      I once packed a 40l with so much stuff before my flight home, I had about 6-7 kg too much. But I managed to sneak it on board by pretending it was super light. 😉
      So even with a 40l carry-on anything is possible.

  3. dsmith says

    Packing cubes and bags are definitely sanity savers. They make my packing so much easier for my husband and I both.

  4. Bec says

    My partner and I backpacked around Europe for 5 months. He started with the organisation of compartmentalizing and I shoved everything in. After about 1 month of digging, frustration and unpacking-repacking I gave in and got a lesson from him. I have seen the light! I shall never stuff again. x

  5. Erin M says

    ziplock bags for the smaller items are great- and the bonus is you can see what you’re looking for. I haven’t invested in a packing cube system yet for the larger items (thinking about it for my trip next month), but my stuff is always packed in sections anyway, I pack fairly light so I can usually find most things without having to unpack my whole bag. Well, for at least the first few days!

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