It's illuminating to show my first sketches. Primarily when I'm designing I want to capture the idea, quick and rough. I get a good directive of the sort of energy or personality I'm trying to retain for when I go into the rather methodical impersonal world of vectors.
I'm always surprised at how much stuff in the doodles ends up in the final work.
In the following example, the first drawing was a tiny scribble, spring-boarding off an idea for arm placements. Everything I needed to know was in the first doodle, when I figured this was going to be Conan O'Brian I did another quick doodle for his head, only then did I go searching for references.
Since I was pretty happy with the illustration of Hipster-types I thought I'd do another one of people. I chose to do a random group waiting for a bus (this turns out to be a fairly common idea I found).
This sketch was pretty complete as a starting point. Notice the small man / woman in the vest, I had no idea what I was going for and figured I'd resolve it in the final image.
But I never did, is it a short feminine man or a man-ish woman? It's the weakest part of the image because I don't know what I'm saying with that character, but then they're random people so perhaps I'm not mean't to know.
Click on the images for larger views.