Excess Baggage: Packing for the Business Trip

I have a complicated history with packing for a trip. I've been doing it for most of my life. My parents divorced when I was young, which resulted in weekly "trips" from one residence to the other. I suppose the smart thing would've been to keep a wardrobe and other essentials at each house: the weekend warrior wear at one and the schoolboy regalia at the other. That idea never occurred to me, though, which resulted in a constant state of packing. I'd get through the school week, pack a bag Friday night, and then head to my Dad's place Saturday and Sunday (sometimes I'd unpack, sometimes not). Monday morning I'd drop my bag(s) off at my Mom's on the way to school and unpack afterwards. Rinse and repeat.

This perpetual dance resulted in a tendency to overpack. The one way I could control things was to be sure I had the gear required to navigate the weekend. Only adrift for three days, but certainly I needed jeans, three pair of shorts, two sweaters,  three t-shirts, a bathing suit or two, pajamas, five pair of socks and underwear, sneakers, sandals, a guitar, and two books. This was the norm.

Fast forward fifteen years. I travel regularly on business, and carry-on luggage is preferred for these trips. Packing now tests the limits of my sanity. Whether a three day trip or a ten day trip, it doesn't matter. The process is the same. One suit or two? Definitely four dress shirts, five ties, three pocket squares, and a pair of dress shoes. Need those khakis for dinners with clients, jeans for the casual dinners with "friendly" clients, a nice pair of shorts for evenings dining at the hotel bar, and "comfy" shorts for bumming around the hotel in the mornings and between meetings. Four graphic t-shirts, also for bumming around, and three golf shirts are a necessity. At least five undershirts and seven pair of socks and underwear. Bathing suit and flip flops. Don't forget the workout attire - athletic shorts, sweat wicking shirt, underwear and socks, a pair of running shoes, iPod with armband for running, heart rate monitor, and sweat proof, in-ear headphones. Obviously need the laptop, iPad, gameboy 3ds, novel (the tactile experience of reading a book is preferred to the impersonal e-book experience), cell phone, noise cancelling headphones, journal, chargers, notebook, business plans and other client related material, including no less than 25 business cards, even though clients have my contact information already. Passport (US and Canadian) and wallet are not to be forgotten. And cash...lots of US cash.

All this should fit into one, standard issue piece of carry-on luggage and a briefcase, right?