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For nearly 20 years I didn’t have to do much business travel. These days life is different. When my trip frequency rose above once per month I evolved a bag strategy which is both imperfect and functional. It is also very heavy on the Tom Bihn gear, because I like his bags and I tend to stick with things that work well enough. Other companies also make great stuff; my former boss swears by WaterField bags, for example. Choice is awesome.

My general theme is simplicity. Painless packing is the single most important aspect of this whole thing so keeping it simple is important. Particularly when it comes to cables, I’ve often just bought an extra cable so I don’t worry about remembering to pick one up and carry it with me. This is useful to me because I’m really forgetful. I am, obviously, fortunate to be able to make that tradeoff.

Bag One: Travel Bag

Bag one is the main bag. I have been using the Aeronaut from Tom Bihn for years now and it continues to suit all my needs. I broke this bag in by going to Europe for a week and a half, with all my clothing in it. That worked and it’s also fine for two to three day trips. If I was interested in getting really specific, I could get a smaller bag for shorter trips; Tom Bihn’s Western Flyer would be a good complement. In practice I haven’t felt the need for that kind of specialization. There’s a lot of empty space left in the Aeronaut when I’m just doing a short trip, but so what? If I only have one travel bag, I can keep the travel gear in it and I never have to worry about swapping things around.

The Aeronaut fits in any airplane’s overhead bins, it has a huge central compartment, and it has functional backpack straps if I overpack and need to distribute the weight better. It’s also indestructible. I spilled a huge bottle of Rudy’s barbecue sauce on it once and it washed out painlessly. I expect to keep this bag for decades.

There are two side compartments. I could use one of them for an extra pair of shoes if needed but I’ve cut down on that weight in the last few months, so it’s generally empty now. The other side compartment has a specially sized packing cube in it; inside that I keep a PowerQube with two 6′ USB-Lightning charging cables plugged in.

This is literally the stupidest thing I carry. I backed the PowerQube Kickstarter so I feel vaguely obligated to do something with the thing. It is a superb power strip, with six outlets and three USB charging outlets, but it’s heavy. I also don’t need six outlets when I travel. I don’t like the Accell travel strip recommended here, because sometimes hotel outlets aren’t in a convenient place. I’m sure I could still find a corded solution that didn’t weigh several pounds. In the meantime the PowerQube does everything I need.

Inside the Aeronaut main compartment, I keep a small travel stuff sack for toiletries: a razor, spare blades, toothbrush, toothpaste in travel size, stain remover pen, and a bottle of Advil. All of those live in the sack, so there’s no futzing around with remembering things if I wind up packing at 5 AM while trying to make a 6:30 flight. These things do happen.

I also keep a packing cube backpack in there. I haven’t ever used the backpack aspect of this thing but it doesn’t hurt to have the option. I’m glad Susan convinced me to get this style. I can fit up to three days of clothing in there; it takes up about half the space in the main compartment. If I were doing longer trips often, I’d get another packing cube to match. This was a fairly recent purchase; I like it better than the alternative, which is a set of tie-down straps in the bottom of the compartment. I get where I’m going, I pull it out, and everything’s accessible.

Since almost everything is already in this bag all the time, packing is easy: grab clothing, fold, put it in the packing cube, and go. It takes about five minutes.

Bag Two: Briefcase

My briefcase is a Cadet. This is also a recent purchase. I am using an 11″ MacBook Air as my work computer, and the Cadet is a perfect case. The main compartment has a sleeve for the Air, which slides out at airport security so I don’t have to unpack the entire computer. There’s also an internal pocket which can fit my sleeved iPad nicely; alternatively, when I’m just trekking back and forth from work I slip the iPad in the external back pocket for convenience. Mark this moment: I rebelliously eschewed the Tom Bihn iPad sleeve in favor of a sleeve from Rickshaw Bagworks. I made that choice for no better reason than my embarrassment at the number of Tom Bihn bits and pieces I own. It’s still a really nice sleeve and very customizable, so I recommend them as well.

I also have a couple of organizer pouches clipped into the main compartment for cables; one has Ethernet and DVI adapters for the MacBook plus an Ethernet cable, and the other has another USB-Lighting charger cable, a headphone jack cable, a cigarette lighter to USB adapter, and a Lighting-DVI adapter cable. The charging cable is redundant but again, I’m aiming for simplicity and minimal fumbling. I’d rather open my briefcase in a rental to get at a cable than go into the back where my travel bag is sitting, plus this means I always have a charging cable at work.

In the front pocket, I keep a Field Notes notebook, my iPhone EarPods, a few pens, and a MacBook power cable. The power cable is a spare: I also keep one at work but I never want to be annoyed at myself for forgetting to pack up the work cable, so the travel one is always in my briefcase. The notebook is still an experiment. I’ve been using it for work and personal notes for a few months now and it’s way easier to fish it out of my pocket than it is to fire up a note application on any of my devices. Also, things stick better in my memory when I write them down on paper first. Field Notes are from the functional branch of the hipster tree.

I carry the briefcase daily; my MacBook comes home from work with me, and so on. This means it’s a little heavier for day to day use than it needs to be. There’s no reason why I need to carry some of those cables when I’m not traveling. However, you know the theme: if I always have them in the bag, I don’t forget to put them in the bag.

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