Confront Your Fears
The single biggest limiter in street photography is not technical. It is fear.
Fear of rejection. Fear of confrontation. Fear of looking foolish. Fear of taking a bad picture. Fear of offending someone. These fears are not irrational — they have real causes — but they are almost always disproportionate to what actually happens.
In ten years of street photography, the outcomes of being noticed break down roughly like this: 80% of people do not care at all. 15% look at you, register the camera, and look away. 4% give you a look or move away. 1% say something — usually curious, occasionally annoyed, rarely hostile.
The way to shrink fear is through exposure, not avoidance. Every time you take a photograph you were afraid to take and nothing bad happens, the fear diminishes slightly. Every time you leave without taking the shot, the fear grows.
Practical techniques:
Make eye contact before you shoot. Smile. This is not weakness. It is acknowledgement. Many street photographers find that explicit acknowledgement — 'I love the way the light is hitting you' — gets them better access than any amount of invisibility.
Work closer than is comfortable. Vivian Maier shot on 12mm. Weegee shot with a flashgun in people's faces. The photographers who got the best frames were the ones who got closest.
Accept that some people will say no. This is not a catastrophic outcome. It is a data point.
The point: the photographs you didn't take because you were afraid are the ones you'll regret. The ones you took and got wrong are just photographs.
Any. But consider: a rangefinder or compact camera is less threatening than a large DSLR with a long lens.
Take five photographs this session that you would normally talk yourself out of. Then take the same five photographs you always take. Compare.