On Streets With A DSLR, how does it feel photographing on streets ?

Early stage on this hobby, i really feel shy everytime i walk alone on the streets with my dslr especially having telephoto lens on my dslr body. But, when i am with a group of photographers for a photowalk, i no longer feel shy. It boost my confidence in taking photographs on the streets. Now, as i get used to street photography, being in a city phrone to robbery, the shy feeling i felt before, turned into fear. We might have to consider our location for this matter. Our gears are bit expensive, and this might attract robbers. So know the place first, or better yet, dont show off your gadget when walking alone.

I do that all the time so I think I'm getting quite good at not being noticed. But I don't take a lot of pictures of people. I've been trying to use my normal lens more because with the telephoto lens I usually get pictures of birds or small details on houses, not a lot of pictures of the whole cityscape. I think that the tricks for taking good pictures with a tele lens is to "hide" so that people don't notice you. At least if you are out to take pictures of people. If they notice they either turn around ( I do so myself) or put on a fake, weird smile.