I have personally spent the better part of my last 33 years acquiring more and more things, upgrading to shinier things and packing away old unused things. On occasion I have culled a large portion of my stuff - usually during a move - but it seems like the amount of baggage carried around always increases over the years.
So now as we prepare to depart San Francisco with only a backpack and absolutely nothing physical left behind apart for some documents I have the rare need, or opportunity to cut my possessions down to only those I actually need and a few that I really want. The need part is vastly simplified from my everyday life here in the city. I NEED some cloths, not only for comfort but also to keep myself from getting arrested. I need to bring a computer or tablet for the purposes of this blog because access to one will be limited in many of the places we will be visiting. I need a camera for the same reason, and I happen to want a camera nicer than my phone possesses. Pretty much everything else falls into the misc. categories of small conveniences, precautions and security.
My pack for the trip is the REI vagabond tour 40. A modestly sized backpack meant for comfortable touring. It features a few things like lockable zippers to deter casual theft and the ability to be used as a duffel bag. It also seems to hold quite a lot of stuff for its small size.
Inside of this I have 3 packing cubes arranged that compress my cloths into a small volume. I'm sure the organization of these will change with some use, but currently I have one dedicated to pants, shorts and underwear. Another is for shirts and jackets, and the final is for miscellaneous items.
I also have a Timbuk2 commute 2 messenger bag that will be my electronics carrier for flights and times I want them within arms reach. This will also double as my day bag and camera bag with a power pack, extra camera batteries and memory cards set in built-in pockets.
Rounding this out is my footwear which consists of a pair of leather camper sneakers and a pair of flip-flops.