I want to write you this article on how to practically have more courage to shoot street photography:
Street photography favors the brave
First of all, realize that street photography is probably the most frightening form of photography.
If you take a photo of a flower, it won’t possibly yell at you, or punch you in the face.
Being a street photographer means that you are brave. It means that you have more guts than the (average) person. It means that you are a risk-taker for your photos.
So to start off, pat yourself on the back for having the courage to even pursue street photography.