How to Pack One Bag for a Five Day Trip - Why you don’t need all that junk in your overhead luggage

For the last three months I’ve been traveling every other week to Denver for work. These trips last five days — Sunday to Thursday — and my team has asked me how I can last that long with a single bag.

This article makes an assumption that you have some sort of backpack or messenger bag that can double as your luggage and your daily carry to the office. If you don’t have one of those, single-bag trips become a bit awkward — your coworkers might laugh when you’re wheeling your bag around the office every day.

Anyway, with that said:

Here’s how I do it, and how you can too!

1. Pack Only What You’ll Use

Most people pack way too many items when they go on trips. This comes from over-planning; every conceivable scenario is accounted for, which leads to a lot of backup items.

But ask yourself, when was the last time one of those things actually happened?

Most likely the answer is never, or maybe once or twice.

Face it. It’s very unlikely that you’ll have any problem that justifies that extra set of underwear, backup toothpaste, or lucky shirt.

Here’s a picture of everything I need to last five days:

Everyday carry
(I promise I’m not an Apple fanboy. I still have never purchased one of their products. The streak continues!)

Notice the lack of shoes, belts, jackets, and other accessories? That’s because I wear them on the plane with me.

Yes, that does mean that I’m stuck wearing the same accessories each day, but who cares? Shoes are the number one killer of bag space, but you seriously don’t need more than one pair. Nobody will notice that you wear the same pair of shoes every day, so take a sturdy pair that work great in the office and out on the town.

2. Roll Your Clothes

I’ve found that rolling up my clothes into tight little burritos saves me a great deal of space when packing. There’s a debate on which method is actually more effective, but for me and my bag, rolling takes the cake.

Here’s a picture of my now-reduced clothing footprint thanks to rolling:
Everyday carry rolled
(Notice the smaller gaps between clothing than the last picture. That’s how I “proved” rolling is better.)

Yes, I didn’t roll my socks. That’s something I could improve on, but I’m not a fan of the whole “inside out” thing that happens when you roll them. It just bugs me.

3. Pack Tightly — Order Matters

Once everything is rolled up, pack it tightly into your bag. Think about how to best utilize the space. For me, I switch orientations depending on the length of the clothing burritos in order to pack everything as tightly as possible. For you, the technique will vary based on your bag.

Make sure to leave items you might want to access before arriving at your final destination on the top of the packing. I keep my chargers, snacks, and toothbrush within easy reach for use in the airport or on the plane.

Everyday carry packed
(I missed an opportunity to advertize my delightful deodorant: Old Spice Timber.)

It will likely take you a few attempts to find the perfect packing combo. But once you know the right way to squeeze it all in there, future trips are a breeze. Since everything has its place, you’re less likely to forget any of your clothes!

4. Use Your Bag’s Straps

Once everything is in, tighten down the various buckles to keep it all safe and secure. At this point your bag is probably fuller than you’re used to, which means there’s a greater chance of things falling out if you open your bag again. Keep that in mind when accessing items while on the road, but it shouldn’t be much of a problem.

Unless you have incredibly puffy clothes or an ever-expanding pocket dimension in your bag, everything should stay relatively compressed and safe.

Everyday carry closed
(No pocket dimensions in this bag.)

5. Enjoy!

Now you’re ready to develop the superiority complex that comes with the power of single-bag packing.

You can be the last person to get on the plane and never have to search for an overhead luggage compartment again.

You will always be down for a night on the town, even before hitting the hotel. One bag to keep track of is nothin’.

You’ll make your coworkers jealous with your sweet packing skills.

But most of all, you’ll have an excuse to sit in bed watching Netflix rather than exercising, since workout clothes are not fitting in there.

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