What is Street photography? Each photographer defines Street photography differently, but generally it is defined as capturing everyday life with a camera - photographing people doing everyday things without it looking posed. In other words candid photos, but not of friends and family, of strangers. What makes "Street photography" difficult is not the photography, but that you are photographing strangers. The problem that most people are uncomfortable taking photos of people they know is exacerbated when the subject is a stranger.
For many it feels like theft, like they are stealing something from the person being photographed. Their answer is to use a very long lens. But isn't shooting with a long lens even more dishonest? Although it is possible to take great candid photos of people from a distance, it's often difficult to create a relationship between the viewer and the subject. The only way to create great images of people, where the viewer believes that they actually have a dialog with the subject, is to shoot in close proximity. This often means less than 2 meters distance from the person you are photographing.
Perhaps one of the most famous portraits ever taken is the girl from Afghanistan by Steve McCurry for the cover of National Geographic. Although the photo was taken more than 30 years ago, people still remember this photo. Why? Because as a viewer we feel as if we are having a conversation with her and we have a sense of who she is. Even though we really do not know anything about this person, each of us walk away from the image thinking that we do know something.The fact that she seems at ease with the picture taking process allows us to connect with her. Steve McCurry achieves this by shooting in very close proximity to her.
So how do you achieve this connection? First, you must change your thinking. If you believe that you are invading someone's space or that what you are doing is somehow wrong, then the person in front of your camera will believe it too. And if they believe this, then they will not be happy with you taking their picture. Second, you need to be a little bit more assertive with your desire to take the photo. You cannot just stand back and be a casual observer. You need to engage the subject. Talk to them before you take the camera out. Put them at ease and make them feel more comfortable. Once this is achieved then you will be able to photograph them more comfortably.