So I like lots of options.

I'm not sure what part of my personality makes me such a bad packer. Well, it actually depends on what classifies as "bad" packing. I'm always prepared. If my kids puke, spill milk, fall in the mud... I'm ready. For all of it. If I'm in a preppy mood, want to be a little rock and roll, decide to channel Reese Witherspoon, I'm ready—even if I'm 600 miles from home. That skill works well when I'm packing the car or have a four-suitcase limit, but when I'm trying to put it all in a little carry-on, I'm in trouble. This is my fate at the moment. I've narrowed my clothing down for a long-weekend to enough choices to last me a week and a half. Now what?