Now that you've seen what's inside Adam's, Kevin's, Jason's, and The How-To Geek's laptop bags, it's time for me to bring it on home with my collection of new, old, analog, and digital gear for hitting the road.
First, I need to disclaim this big old pile of electronics: I travel a lot, and not just across town to the office. Since most of my trips involve long flights and last a week or two, much of my gear is for long-term outings.
The bag: After years of shoulder-dislocating messenger bags and sub-par backpacks, I finally got this not-cheap-but-hardy Booq bag as a birthday gift. Booq's MacBook bags are spendy, but this one's been worth every penny. I've taken it literally around the world and back with me over the last five years and it's still in great shape. It's got a stiff black form, tons of zipper and Velcro pockets, sewn-in magnets which snap the top flap shut, and it looks about as professional as a backpack possibly can. The shoulder straps and laptop sleeve part are heavily padded so I don't worry about my 15" MacBook Pro, which fits snugly inside, without bouncing around too much.
The Kindle and phone: Packing more than one book or magazine leads to backaches and an overstuffed bag that won't fit under the airplane seat in front of me, but I can take dozens of books and newspapers with me on my Kindle. While it sucks that you have to wait till you're at a cruising altitude to start reading, I've been reading more books than ever since I got the first version of Amazon's ebook reader. Also, my trusty Android phone goes in my bag's smallest topmost pocket, and it's the thing I grab the most to work or play on the go.
The analog notebook: Like Adam, I don't need a fancy leather-bound notebook. I go through a single small spiral notebook every two months, so I usually just pick up a cheap one at the drugstore. I don't skimp when it comes to pens, though: I'm a sucker for the tiny and shiny Fisher Bullet Space Pen.
The repurposed iPod backup drive: This antique, second-gen iPod is the oldest and most unusual thing I carry on long trips. This iPod is over seven years old and the battery can no longer hold a charge long enough to play an entire song, but when it's plugged in it works like a charm. So I've repurposed it into a travel backup drive. Since I work on the road, I worry about the possibility of my notebook's hard drive dying while I'm away from my regular Time Machine drive back home. So I plug in this sucker (wrapped in a bright rubber iSkin, also from back in the day) with its FireWire cable, and sync 20GB of my most important documents to it while I'm out of town. This way if the laptop does die I can dash into a Mac store in any city, plug in this old beast, and get what I need without worrying about waiting for a long Mozy or Dropbox download. (Yes, a regular old thumb drive would get this job done, too—but it wouldn't qualify for the Computer History Museum.)
The little things: If I'm doing a presentation at a conference, I always take my MacBook's IR remote and the DVI to SVGA adapter (for older projectors). I've always got an extra pair of earbuds. Like Adam, if I've got a travel companion, I also take a headphone splitter so we can both listen to music or watch a movie on the plane. I like to take photos at conferences and on family visits, so I take my old Canon Elph (not pictured) and my Eye-Fi card and reader so I can configure the nearest Wi-Fi network to automatically download my photos as I snap them. Also, an extra USB cable and Mac plug adapter never hurt.
Looking over all this stuff, I realize I've become one of those ridiculous nerds who should start a chiropractor fund after hauling around an insane amount of electronics on my back. But if you look at this bag as the traveling office of a working nomad, it makes a little more sense.