I am the definition of a long time lurker, having registered 9 years ago and this is my first post. How do others overcome the apprehension of street photography? I have tried several times, but it just feels so awkward taking pictures of people on the street. Someone like Yokosuka_Mike is so darn prolific with pictures seemingly right in their faces. How do you overcome both your and the subjects' anxiety, or maybe better put, their objections? I try to take pictures in stealth mode, praying no one sees me taking their picture and making a scene.
Just practice. It means go out and take pictures. And find what is interesting for you. And be realistic with surroundings.
One is tall white man pointing cameras directly at polite Japanese. Another is Bruce Gilden taking pictures in rough areas.
Both are fine because they know where they are and how far they are capable of pushing limits.
"Stealth mode" is self illusion. It is visible always if person is taking pictures. The difference is how it is taken and with which gear.
If I wear big camera I don't hide. In the opposite, I make sure it is noticeable. After sometime you will start to see people reaction on it in advance. Some will react alerted, some not and some will cooperate.
Start with Ricoh GRD series. Small CCD sensor, no need to focus. It is so small, it makes you invisible. People don't care, because it is smaller than phone. Nobody takes you seriously. You could take to strangers and take pictures, they won't care or even realize.
Find John Free YT channel. He explained it like nobody else did. But it is simple, be yourself. If you are interested in face snaps, do not hide it.
Personally, I have never been into it. I'm more into wider collision and something unique. Winogrand called it drame, to me the best is idiocity. No need to be right into the faces, but close to the action. No zoom, must walk into it, nearby.
Start with event. But not something obvious as taking parade pictures on the street side. Go to where they are getting ready before start. Get to any event and just practice by getting close. At some point it doesn't matter is it planned even or some event you have bumped into on the street.
And later you might grow into realizing - this is an event. Will come with long practice.
Oh, crowd is your friend.