Fear is a challenge for my photography. For me, when a picture has people in it, it becomes far more interesting; when they are doing something, this increases. But I'm always concerned about being confronted (though I can talk my way out of most situations) or even getting involved in a fight.
Recently, I went to a market with the intention of taking some pictures for the market's website. So in a way, I had permission and a reason to shoot. That made me feel much better and bolder about doing so. Although it wasn't my first attempt at street photography, it was the first one where I felt comfortable enough to approach people.
Most regular folks seemed confused but also a bit shy that I wanted to take pictures of them, but I wanted to capture something of the left-ish atmosphere of the place (it's an organic foods type market). I asked for permission from the first couple here but the second were just snapped.
The market traders didn't seem to be in the slightest bit bothered and carried on about their business.

(note the people in the background who seem to be watching me - I guess I wasn't as discrete as I thought!)
By the time I left, I was absolutely buzzing and couldn't wait to take more pictures around the city. It certainly helped to increase my confidence in taking pictures of people, and will help me as I seek to learn more about this fascinating artform.
disclaimer - these are DSLR pics (boo! hiss! lol!), but I needed the results to be available quickly.