In the summer, I plan for the ride in by putting my work clothes in my messenger bag before heading out, and making sure that I have my laptop, power adapter, voice recorder, notepad, and USB cable for the voice recorder (if I forget any of the above, my day will suck). But that's about it. My ride is just a hair under 5 miles for my standard route.

Actually, I also check the forecast and pack rain gear if necessary.