For years I have been on a quest to find the perfect Geek Bag to haul all of my crap around in, whether I am heading out to visit friends, running down to the local coffee shop, commuting into work, or suffering the tedium of airline travel. I have looked high and low for the perfect catch all bag, the irony being that in my search I have acquired more bags than if I purchased separate bags for specific use scenarios. Much like gadgets, all in one solutions may seem attractive, but rarely excel at any purpose, a lesson I seem to keep in mind with gadgets but refuse to acknowledge with bags. The reason, I suppose, is because I hate transferring stuff from one bag to another, so switching back and forth between bags isn’t practical (nor is just having duplicates in each bag practical with the level of crap I carry).

So in a multi-part series, not at all related to my security ramblings, I shall outline my quest and what I have thought about each bag along the way. To begin with, I will talk a bit about my usage scenarios, so that my particular opinion is understandable. To put it bluntly, my bag is the dream for would be muggers, though I myself am not (having lived in some bad places I am one of those people who habitually notices the movement of everyone around me and can spot threats fairly easily). At any point I am carrying at least one laptop, either my work laptop or my personal one, and often times I am carrying both, especially if traveling. Fortunately both of my laptops are rather small, as I prefer machines I can actually open up on planes with the whopping 12″ of total space they give you between your seat and the seat in front of you (do you know how much a pain in the ass it is to find small laptops with good resolutions and decent hardware?). Along with the laptops comes their associated power supplies (fortunately also pretty small), a wireless Microsoft travel mouse (death to touchpads, death to mouse nubs), a USB flash drive, and a Micro -> mini -> full SD adapter. Also, my personal laptop is a tablet, so I carry a spare stylus for it.

On top of that I have my Zune, plus the associated premium headphones (its nice that MS actually includes decent headphones for free), and syncing cable, as well as a 12″ 1/8″ to 1/8″ cable so I can use it with the aux jack in my car or in rental cars. I have my cell phone (at the moment an HTC Touch), sync cable, and charger. I have my Nintendo DS, games, and power adapter. Plus miscellaneous pens, some pain killers (my knee and back used to kill me on plane flights as a result of a car wreck, but surgery actually worked), usually the most recent issues of some combination of Discover, Scientific American, or Smithsonian magazine, possibly a computer book that I am reading (though I try to get ones that come with eBooks on a companion CD so I can just read them on my tablet PC), keys to my storage unit and desks (I don’t like them on my primary key chain, but also don’t want to forget them), and a novel (though I will soon get a Kindle to save space).

So I have a ton of crap, and holding it can be a challenge, especially if I want to maintain any semblance of order in the bag. Moreover, as I used to fly often, and now do so again, it is important that I can get my laptops out quickly while going through security, while still having padding for them, and it is also important that the bag doesn’t take up *too* much space, since tiny little commuter planes are my most common ride out of the hell hole I live in now (here is your 4 cubic inches of overhead space sir, unfortunately someone else is infringing on it because they bought three body bags on the plane and we didn’t speak up).
Various leather (or plether), formal looking business bags are right out. I’m not a business type so I don’t care for the look, but moreover the bags are rarely designed for ergonomic comfort, and take up a constant amount of space no matter how full they are. If I am carrying less stuff I like a bag that can compress down a bit. I tend to bounce back and forth between backpacks and messengers. Backpacks are more comfortable when loaded up with a decent amount of weight, but are more bulky in general. A backpack with crappy straps is usually still tolerable, while a messenger lives and dies by the quality of its strap. The benefit to a messenger strap is that can be loaded up with various gadget holders, bandolier style, and allow for them to be more accessible (Timbuk2 makes pretty good strap pouches that mount on messenger straps), though at the cost of also making them more exposed.

I am unopposed to walking, and especially if I am visiting the office in Chicago I will forgo a rental car and just travel on foot and commuter rail, so I do prefer a bag I can comfortably carry for a decent period of time, and water resistant in case I am caught in the rain. So in short I want a bag that can hold a lot, but has a compact footprint and allows for easy organization; a bag that allows easy access to possibly two laptops, while also offering padding; a bag that is comfortable and waterproof; and a bag that will hold up to continual abuse. Is that asking for too much? We shall see.

~ Joshbw