Thomas,
If you are going to do this, you need, as Domenico said or at least came very close to saying, to confront your fear.
You know, or maybe you don't - I was a shy kid with a serious confidence deficit, probably due to my lack of male influence in my life as a child. I mean, I had no clue, whatever. So, I got interested in Song Dynasty Chinese silk paintings in an art history class, and wanted desperately to do something like that, so I picked up on photography and hooked up with Minor White. Seems appropriate, probably. But there was a time when with two little girls, I decided that yes, I had to make a living. Printing for Don Normark, I met the Sunset Magazine editors and got into a free lance arrangement with them as a travel and garden photographer. So here's this really shy kid out there photographing in crowds, doing events and travel destinations. Every shot had to have at least one person in it and it had to look natural, and the best way to do that is for it to be natural.
I was terrified.
I adapted.
I am still a bit shy, but I learned one thing that was extremely valuable, both in photography and in teaching. Life was not at all what I thought it was. By adopting a persona, I could be an actor. In doing so, I could do much more than Larry Bullis himself had in him. I could be much more than that. I could be a fearless photographer, plying my craft in public, and in doing so, I could interact with people with some degree of highly enhanced confidence.
Shooting like that is an incredible discipline. If I thought about it, I'd get stage fright and fold up like laundry. It requires not only confronting one's fear and getting past it; it means to confront that fear constantly, daily if possible, and live that confrontation. If I got scared in the midst of a job (happened repeatedly) I eventually learned that dealing with the onset of fear is easier if I convert the fear into action, so I'd shoot more aggressively. In doing so, I became more entertaining. If people get uncomfortable, the thing to do was to lie on the floor and shoot them from there. That was great. It made them into monuments.
I hope you aren't thinking this is one of those collectible things like a boy scout merit badge. You know: "I've done landscapes, I've done portraits, I've done architectural photography, now I'm going to do street photography" etc. If you are going to photograph in public like that you must do it constantly and work very hard. Otherwise, your people will look like stick figures.
I can't do it now, and that's why. It is NOT something I can do on Saturday, and go back to something else on Monday. Unless I were to do it maybe three times/week, ten hours/day. At my age, I can no longer run circles around my subjects, models, etc. I can't shoot two-day hikes in the desert in 100° weather. If I were going to do that kind of shooting now, I would need to train for it. I mean, like an athlete. Or an actor. It's sort of like method acting, actually, at least for me. Others may not have this hanging over them; I don't know. But that's what it's been like for me. I am strongly attracted to it, but all I have to do is pick up a camera and hit the crowd, and I know -- I know that my career doing that is really over, and I'd best occupy myself with - at this point - contemplation, and putting together all I've learned into some coherent whole. I hope I have time.
Anyway, it isn't a small hobby thing we're looking at here. It's a calling, like teaching or the ministry. If you are going to do it, then do it. Really do it. No half efforts. It's a big commitment, and in order to do it successfully, you have to want it with everything you've got. I was good at it, and while I had a job doing it, it was rather wonderful. Now that job is gone. Doing it now, since there are really no picture magazines left, requires doing it without the financial motivation. I'm not likely to start doing it again. Other things have taken precedence and I have insufficient motivation to ever achieve my own standards.
If Gene Smith were alive today, he'd be unemployed. I'm sorry, but it's true.