I traveled for many years with a laptop and almost always carried it in a rolling bag. That changed about eight years ago when I got a backpack designed for the laptop and much more. My travels haven’t been as extensive as in the past, but I am kicking myself for not getting a backpack earlier.
Sometimes your travel will be a short distance by car, but I typically use the backpack when I’m flying. Of course the laptop is in the bag and it has to be easy to remove for a trip through airport security. I also include the power cord/brick and a small stand that keeps the laptop from overheating.
Throw in a few magazines and newspapers to read during the flight. Nowadays more of my reading is done on a tablet which is also in the bag. There are some miscellaneous cables such as USB to microUSB and a small power strip. I’ve written about all these items in previous blog posts.
I throw in a plastic pouch with any travel paperwork. In the pockets are headphones for listening to music, a point and shoot camera and various other electronic doodads. Often I’ll have some mints and a few other personal items.
You can certainly use a regular backpack for carrying your items, but having a quality backpack like the Targus Drifter II Backpack is much better as it is designed with compartments for various types of items. I’m guessing my backpack is getting closer to its end of life due to the wear and tear it has endured. Should I need a replacement, this backpack would likely be at the top of the list of those I’d consider.