When I got that question I didn't have a difficult time answering. As a matter of fact, the answer came as quickly as the machine-like act of packing itself.
When traveling, I pack the following first:
1) Books I'm dealing with at the moment.
2) Laptop regardless of the nature of the trip, business and/or pleasure.
3) iPod fully updated with fresh playlists.
4) Notepad and 3 different color pens.
5) The cord jackets.
6) The Bob Dylan t-shirt.
7) Urban shoes.
8) Hair products.
Something that dawned on me just now is that the contents of the luggage are a mere reflection of daily life/general existence. As I was just told, 'You can tell so much about someone based on what and how they pack.'
I have to say I concur.