I’ve done a fair amount of traveling in my life, specifically in the last 11 or so years.  During those years, I have been all over the world, both personally and professionally, and I learned that checking bags is inconvenient.  I stopped doing it.  I will never check a bag if I’m traveling for less than 7 days.  I have always taken a backpack as my personal item / overflow bag.  I’ve had quite a few, Targus, Ogio, Jansport.  I tend to prefer Ogio backpacks and have owned 4 of their backpacks in different styles, 3 of which I still have, and my original is still in use today be someone else.    I like a bag that can hold quite a bit of stuff, but that isn’t inconveniently huge. I’m pretty picky about it, actually.

I tend to carry in my bag, on any given day:

• 15″ macbook pro
• ipad 3
• Power adapter for ipad3/iPhone
• power adapter for macbook pro
• Extended power cable for Macbook adapter
• MiFi (sometimes)
• Evernote Moleskine notebook
• Kensington laptop lock
• Various USB keys
• Keys for car, home, office and laptop lock
• Passport
• various pens / highliters
• A length of paracord or twine woven into something (generally small, ~5′; for securing things together if needed on the return trip)
• various cables, USB, car adapter
• Garmin GPS (if going somewhere new)
• ~2 packs of gum
• Small flashlight
• Bottle opener

It’s really not that much stuff.  I have paired it down from when I used to do a lot of work that needed things like console adapters, tools, needed extra batteries, etc. so I switched a few months ago to a fairly nice Targus messenger bag.  I actually really like this bag, and I love the idea of a messenger style every-day carry bag.  This bag works great for my for every day commuting.  It holds everything I need, has an easy open front and has both protected tablet and laptop compartments.  A messenger bag looks a tad more professional than a backpack, and while I don’t really have any reason to need to appear like a suit, it’s always a good idea to step outside of comfort zones and try new things.

So, in a recent trip to boston for a few days, I decided to try this messenger bag for my laptop/personal item.  Where this became problematic was during long layovers.  I will fully admit that part of my problem may have been that I’m just not used to a messenger bag, but whatever it was was apparent right away.

The messenger bag was unwieldy when trying to hurry through the terminal and drag a rolling bag with me.  The messenger bag puts pressure on one shoulder / side of the neck.  The messenger bag doesn’t have any real room for incidentals that I may want to jam into the bag.  These are all things that I have taken for granted when traveling with a nice, roomy backpack.  I had to tack things onto the outside of the messenger bag to carry them and that became even more unruly.  My neck and shoulder started to get sore on the trip back from carrying around the messenger bag.  It started to feel a bit heavier faster than a backpack usually does.

Once I got back, I moved back to my primary OGIO backpack to truly compare.  The nice, form fitted straps with the clip really made a huge difference.  As much as I really want to love a messenger bag, I really don’t think I can ever truly switch to one for a primary gear toting bag.

Perhaps I need to pair down pair down what I carry again.  If I had, say, a macbook air, I could probably switch, but given that my primary work-provided laptop is a standard 15″ macbook pro, that option is not likely.

I’m very curious as to what other IT road warriors use as a carry bag for day-to-day and for travel.  I know my pal Jon Dugan uses a now discontinued Timbuk2 backpack for travel and is pretty happy with it.  He can fit a few days of clothing and his macbook air and other items in there pretty easily.

What do folks carry?  What bag style and brands/models?  Sound off.