As with everything in life, when you start to learn things you do so in steps and phases. As as teacher it is very important to scaffold lessons in order to build a foundation of knowledge to build up to teaching students more complex concepts. The same applies in learning photography.
I began my photographic journey just under two years ago now. I was at a low point in my life and I needed a distraction, a creative outlet in my life. I've never been musically inclined with instruments or my voice, I can't draw a stick figure to save my life, and I'm not real patient with "crafty" things, nor am I a gearhead. At the very least, I thought, I could pick up a camera and shoot. I learned a bit about DSLR cameras and in my budget I chose a Canon t3i with a kit lens.
Now, being from Colorado the most natural thing to start shooting is the mountains, the aspens, etc... Which I did for a time (and still do occasionally.) However, I found myself quickly becoming bored and not really interested in the subject matter. (If you ever visit Colorado you'll see every gallery, restaurant, and lobby is chock full of mountain and aspen tree prints.) So I decided to go to community events such as parades and festivals to take pictures around the event itself. It was during the St. Patty's Day parade here in Denver I found myself snapping more pictures of people than the parade. I didn't find the parade interesting at all as a matter of fact.
Oooh...there's a GQ looking guy and his girlfriend with movie star sunglasses drinking a beer and kissing at 10am. *click*
Look at the expression on that guys face! *click*
Aw that baby looks sad and her parents don't even notice.*click*
I think everyone in who has shot street photography has had a similar experience of that time we noticed people and public and began capturing them. I had no idea what street photography even was, but I knew I wanted to do it again. Over the next several months it become a leisurely hobby and weekend distraction to go into Downtown Denver and events and find interesting people and things to shoot. However I wanted more. I wanted to be, not necessarily known, but I wanted to be good at what I did.
The lifelong learner in me came out and I immediately began devouring blogs, youtube videos and channels, books, tips, etc... I searched out groups and websites that I could learn more. I while I still have so much to learn, I began to learn so much.
One of the the first things I began to notice about my photography and street photography I saw online at 500px, Flickr, and other social sites is that it all looked the same. Homeless, street entertainers, reflections in water, people jumping over water, large events where lots of cameras are expected, backs of people from afar, on and on.
As I read and studied about street photography I noticed many of the well known photographers had much different types of shots. The kind of photograph that makes you think, feel an emotion, provokes a memory. I want to be like that.
So I started to form my own guidelines. Which I still edit and attempt to refine and even sometimes fail myself, but I keep trying:
1. No homeless - Too easy, too vulnerable. Unless you're doing a specific project to bring awareness to the homeless in your community why are you shooting them? Many of us beginners think we're taking some sort of powerful, dramatic shot. You're not, you're going the easy route picking on something that's just there and used to being stared at. You maybe even gave a dollar as a payoff for the shot.
2. No Street Performers - SP shots of street performers have to be akin to food shots on instagram. We've seen them. Its an easy shot. As a beginner it may help you get comfortable shooting people, but please safe them for your personal folders for your friends or as practice fodder for processing.
3. Only take a shot from behind if its interesting - Many of us are shy of confrontation or being looked upon as creepers pointing a camera in someones face and taking the shot. So I see so many photographs of just backs and people walking from behind. Unless it somehow TRULY is dramatic or beautiful silhouette, try to limit this type of shot.
4. Stay away from the "also rans" or stereotypical types of shots you've seen before - Have you seen those photo's where someone is holding up an old photograph against their face of a younger version of themselves so it lines up? Or against the landscape a photo of the same spot 50 years ago? Yes, you have. A lot. So you took a picture of people walking by a puddle and flipped it upside down. Great. What makes yours stand out from the hundreds of others?
I'm guilty, especially when I first started, of breaking every one of those guidelines. Point is, I'm striving more and more not too. Study the greats, and I don't mean HCB. I mean even the classical painters. You don't need to reinvent the wheel. Rules of thirds, leading lines, patterns, have been there; thought about, written about, talked about. If street photography is a passion or even just a passionate hobby you should strive to challenge yourself.
One final thing, shyness or intimidation of breaking personal space is natural for just about everyone. If you want to take that great shot, you're going to have to push through that barrier and make it. I've suffered from mild social anxiety and depression for years. Street photography is like a therapy for me. I have an extra barrier to push through to make that shot, but I wouldn't feel good about myself if I just took out my 55-150mm zoom lens and stood way back taking pictures of people walking away from me. There's no challenge, no satisfaction in that. Push yourself, patiently look for and take the hard shot.