My first two years with a DSLR can be easily summarised as experimentation; I experimented with candid photography, landscapes, cityscapes, macro, travel, street portraiture & even some studio portraiture.
I had no doubt it was street portraiture that I enjoyed the most and found myself most competent at, it all just felt natural & fluid. All it required was some location scouting, a willing smiling subject, my camera, a trusty lens, a theme & some good natural light. At times adding a fill light would be advisable & thus a flash or reflector could be used to good extent.
That said, you still need to understand that potential subjects would not simply accept to go out with you to the outdoors for a shoot without you first providing some proof of experience & knowledge. In fact, once you have that portfolio we discussed on a previous post, you’d be having more subjects that you could count! :)
So how to start then? Simple! Approach your friends & family, share with them your vision & ask them to support your plan by acting as willing subjects / models. Once you’ve taken a fair amount of good shots of different subjects, you’re good to go … now it is only a matter of advertising & promoting yourself as an able portrait photographer.
Of course it helps to have a new portfolio dedicated towards that service you are promoting. In my own case, I set up my flickr account just for that. Whoever I approach gets a link to this portfolio, and by that, I guarantee their interest.
One more thing to note is that you shouldn’t expect big bucks while you are still building yourself, actually, you shouldn’t even be thinking about that, as during this timeframe you should have higher priorities; experience & the right portfolio.