If there’s one critical lesson that I’ve learned after a decade of practicing street photography, it is that you do not need to remain a fly on the wall.
Practice Confrontation
The easiest way to overcome your fear of street photography is to practice confrontation. Chat with security guards, janitors, and anybody you’d like to photograph. If you want to make a picture, don’t hesitate and engage with the people on the street. The more you practice getting confronted whether negative or positive, you will learn from these experiences.