This is me! I try to be organized. I make a list. I have a plan. And then I go off the rails. My husband says that when I pack it looks like my entire wardrobe has exploded on the bed. He also needs to be told multiple times what to bring, and I sometimes have to redo his suitcase to make more room. That just adds to my dread of packing.
I am a regular business traveler, and I find that packing for those trips are so much easier than vacation packing because I basically wear one outfit all day and bring a set or two of workout clothes.
Our last cruise we did bring clothes for formal night, but my dress was not made of heavy material and rolled up quite well. Since I like to do laundry on the ship (yes, I said it), we normally do not come home with a lot of dirty clothes and can unpack pretty quickly. I also try to wear my bulkiest shoes when I board the ship, but this trip I was wearing a walking boot on one leg so I had to pack the left shoe.