Since I normally travel domestically for work:

Duffle Bag:
Clothes and toiletries
A few tea bags
Sleep mask
Vitamins/Advil

Personal Bag:
Laptop
iPad
Files, notebooks
Maybe a book
Chargers and multi-plug adapter
Writing Utensils
Business Cards
Other cards I might need (MTA, United Club, etc.)
A couple CLIF bars
Headphones with mic
Those little post-it flags
Loose change
A couple USB flash drives
Employee Badge / client's contractor badge
Cough drops, gum, hand lotion, lip balm
Umbrella
Laptop power adapter and mini-mouse (not that Minnie Mouse)
A few individual packets of wet wipes I've snagged from planes with inop faucets in the lavs
Verizon MiFi hotspot

Pockets:
Money clip with cash and a few essentials (DL, GE card, CC, ATM Card)
Phone
Car keys, if I'm renting a car
Hotel key card
(if traveling internationally, passport generally goes in my pants or coat pocket)

Otherwise on my person:
Watch
Nike Fuel Band
Wedding Ring
Glasses