I'm not obsessive at all. I promise. Yeah, anyway. I'm leaving for about a 3 week trip tomorrow morning where I'll be visiting New York City, Toronto, Montreal, and Washington DC before heading back to LA. I'll also be spending some lovely time in the airports in Dallas, St. Louis and Chicago but that's another story. I've maintained for a while that it's harder to pack for a 3-4 day trip than it is to pack for a multi week trip but I keep refining the details on that and thought I'd continue documenting it here as I can. When I packed for my 2 weeks in Japan I thought I had all the bases covered but by the end of the trip I felt I had too many bases covered. For that trip I brought two carry on bags, the larger of which included a smaller one for walking around, and I thought I was on the right track but now I think I can streamline it even more. A few things I realized on that trip:

• Do not pack for single activities. I brought bike riding stuff (gloves, shorts, etc) and while I did ride a bike while I was there I never touched the stuff I brought.
• Streamline laundry as much as possible. The less times you need to do laundry the better, but you don't want that to mean brining more stuff. By streamlining it I mean rather than brining lights and darks, some cold wash some warm wash - try to combine as much of that as possible. If everything you bring is dark and cold wash it's much less headache to get cleaned.
• Avoid specific outfits. Everything you bring should work with everything else.
• Wrinkle proof material owns.
• One pair of shoes is plenty.
• One pair of headphones is plenty.
• Cables - bring chargers, don't worry about adapters.

I think in general I'm applying some of the same general life perspective changes to packing - I used to try and prepare for the worst all the time and want to have several redundant back up plans in place. Now I'm just running with what I know will be happening and deal with things as they come up, if they come up. It's a considerably less stressful way to approach just about everything and I'm kind of enjoying it. With packing and travel, it also lends to a smaller amount of crap to take with you.

I haven't actually started packing for this trip but it's a little longer than the Japan trip, and I'm hoping to bring less. My goal is to lose the larger of the bags I took to Japan and just keep the smaller two - I'm not sure if that's reasonable at all yet but that's what is bouncing around in my head at the moment. I'm finishing laundry now and will start prepping soon so we'll see. Photos, of course, are forthcoming.