I am always nervous when I am go out and taking photographs on the street. Sometimes I try to emulate other street photographers, only to fail miserably. I can't be them. Not that my photos are great, but I am slowly starting to recognize my style, and the kinds of photos that I am successful taking. This is reassuring to me; I feel as though I am making progress.
The 'street portrait' is something that I have come to enjoy. Asking someone to take their photo is easier for me to do than to simply sneak the photo. I look for the people that are already contemplating, then ask them to keep doing whatever it is that they are doing.
Night is the easiest time to shoot, as the street lights act as giant grids. I love grids. Black and white, at night. I am in heaven.