How do you start to get comfortable with street photography?

I am big into street photography as I live in a major city. I am constantly trying to get more shots throughout the city (buildings, landscapes, people on trains etc.) but I always feel somewhat uncomfortable taking photos of people, or even setting up my tripod and taking a photo of myself with a backdrop. I've been trying to get out of my comfort zone and thought it would get easier but I'm always hesitant looking through my camera and taking photos with people in the background. Any ways to get over this besides just continued practice?Thanks via /r/photography http://bit.ly/2V8KbfI