Photographing interesting people in the streets n one of my favorite exercise. It is relatively easy to do and you are not expected to carry a few strobes and umbrellas with you. You need to work the light conditions that you have. I rarely use even a fill-in flash. It is more important to photograph the actions, the mood and the feelings of the situation.
I photographed this gentleman in San Francisco. I just loved his demeanor. Enjoy this exercise and keep on photographing!