Throughout my time as an airline traveller, I've always been a great believer in the "Russian doll" principle of packing - keeping the contents of your suitcase organised and separated in bags of their own, nested to near infinity if necessary. And despite an incident last week, I still believe that's the best way to go.
The basic idea is simple: group items of similar size or function together, and then package them together, either in a plastic shopping bag or (depending on the items) their own cloth bag or container. This has at least three advantages: everything is easy to locate (especially if you use different coloured bags), you can fit more items into the suitcase, and if there is an unexpected washbag emergency you know most everything in the suitcase is protected. An extreme version of the approach is to use those vacuum storage bags for clothes, but that's probably more suited to a large-scale move than holiday or work travel.
For my carry-on case, I tend to favour functional groupings over pure space-saving measures. Phone gear is together; so are power cables; so is camera equipment; so are storage devices. A small pull-out cloth bag contains stuff I'll want during the flight, so I can stow the main bag overhead and stop thinking about it.
In some cases, you really do end up with bags inside of bags inside of bags. My standard carry-on bag includes a small cloth bag of travel essentials, which holds a small zippered bag which contains phone cables, which includes my PC headset in its own separate bag. It might sound complicated, but I can lay my hands on the headset in a second and it never gets tangled. And most of the bags are freebies, previously used for in-flight toiletries.
I think this principle was inculcated in my by my stepmother, a fiercely efficient packer who can layer a suitcase like nobody else. Admittedly, she also occasionally demonstrates one of the downsides of the approach: you can end up with so much stuff in your suitcase that it ends up deceptively heavy, leading to much wailing and gnashing of teeth at the check-in counter.
I experienced the other downside on a recent flight out of Coffs Harbour, when airport security decided that the quantity of electronics in my hand luggage warranted separate manual inspection. (I had, naturally, taken the two notebook PCs out before the bag went through the scanner.)
Over the course of the next 10 minutes, the security dude proceeded to open up probably ten bags-in-a-bag and exposed dozens of electronic items, from USB sticks to USB drives to two types of iPods to headset adaptors to a couple of review phones to power supplies and associated cables. He eventually gave me the all-clear, but not before declaring: "I reckon there isn't any type of boys' toy you don't have."
I agreed, while thinking it was just as well I had a proper system of storing them. Of course, recreating the system took up the next 10 minutes as well, but travel isn't always going to be easy.
Lifehacker Australia editor Angus Kidman has only left his BlackBerry behind on the security concourse once. His Road Worrier column, looking at technology and organising tips for travellers, appears each week on Lifehacker.