How to Become a Fearless Street Photographer

I think because I am new at this I am more inclined to agree with what you have said in the past and what 85mm says here as well, do not look them in the eye. Look past them like you are shooting something else. If they do gesture to you then you can always gesture to something behind them and smile. Don’t engage them in conversation unless they seem friendly.

Sunday I was in the park shooting flowers [and people on Mother's Day] with a 100mm macro. I saw some people look at me with serious lens envy and worked that to my psychological advantage reminding myself that when they did look at me through the lens it was probably because i had a huge lens [+ hood!] on. If anyone was to ask I would tell them it was a macro lens for flowers! *Until I get a wide angle I have been improvising.

**I’ll also mention there was a guy with his camera set up on a tripod doing time lapse photography. I know he got me because I was in his target zone shooting both the flowers and people posing under a tree. No one seemed to bother him though as he lay on a blanket chatting on his cell phone while the camera went click click click at intervals.

You speak of the homeless man though. As a woman I often feel very vulnerable if I am shooting alone. I am tunneled on what is going on through the lens and I don’t see what is going on around me at those moments. Perhaps you have additional advice for women, particularly if they walk alone? Walking alone keeps me out of the big city when there would be tons of opportunity in Chicago.

I never really stop moving and take pictures extremely fast. I think speed is the trick. People think that it should take at least 3 or 4 seconds to take a picture. If you can frame and take shots in less than 2 seconds your almost invisible. It takes a lot of practice, but you can get very fast a accurate. It’s almost like marksmanship or maybe handball.

It’s always nice to see that approaching street photography is appealing to a large number of people, and also that tricks are still a trade to support it as well as the picture-taker.
As far as being fearless is concern, I’d say that if you’re afraid of taking pictures involving your own kind in the streets it might be because you might not have any business doing it in the first place, unless it is some kind of remedy for your shyness, a therapy.
If you don’t know why you are going out there, you won’t know how, and conversely. Your command on your subjects will give you clues about how, attitude, even tricks maybe that will support your natural inclination. And there are so many focal ways to do street photography also. And there are subtleties in Street Photography other than getting up to the faces of the people. It doesn’t prove anything and it doesn’t guarantee the harvest of a good scene. And strange enough is the fact that just the full of guts type of shot, often a single human being portrayed close and maybe weird looking if not angry-looking, get full hype street cred and awe from the SP community or wannabees. That ain’t too much street photography, that’s anthropo-profiling in my sense, without documentary cred. It doesn’t say anything, it’s just sports at best. Attitude and command of your themes or subjects will get you where you need to be and what you want to get. Happy shooting!!!Thanks for posting. Cheers.

You failed to mention a few VERY important things,
1, You can, AND will get your ass kicked sticking your camera and nose where it doesn’t belong.
2, ALWAYS carry a small 5×7 portfolio of your work so that people can see you are really a photographer, and that you put out quality work (many of these people are mentally ill and YOU have no idea who THEY think you are). I have used this to turn around a few very grumpy homeless men, as well as a few camera shy women.
3, Just because you have made a few trips to the same location and engaged in playful banter or friendly conversation with the “locals” doesn’t mean they will not kick your ass and steal your camera, car, wallet and phone on your next visit.
4, Crosswalks are amazing places to post up and wait for an interesting face, you’ll have so many to choose from and they’re all walking right at you.

I love shooting street people but remember folks, everyone wants respect. When I can, I spend a few days in the same area and get to know them. I have used several different ideas to get cooperation, sometimes before the shot and sometimes after. I use instinct to decide if I should ask first, but usually do not. If they shy away I offer to send them a copy. They usually have a community center where they can receive mail. Shooting a group without permission often gets anger, howls of protest and stories of what they have accomplished in life. For some it is fantasy, but I have learned that for many, they truly had some remarkable successes in their lives before bad choices and sometimes bad luck brought them down. This is why spending a few days in their world is worthwhile. It builds familiarity and a human connection. Everyone wants to tell their story to an interested party. This is why it is important to truly be interested, not looking down your nose at a fellow traveller in life. They spot the difference faster than the common “successful” and self important person. Usually a couple bucks after the shot is a peacemaker and is appreciated. I once had a guy chase me down in Old San Juan to berate me. I apologized and moved on. The aggresive street photographer can come off like a thief, stealing someones right to a little self respect much like the hated papparazi. Be human, be fair, you’ll get the shot you want, not the snatch and run – which will look like a snatch and run. That makes it easier for all of us and for them too.

Hey,
I agree you need to find a way to deal with SP and getting up close to a stranger and eventually every SP finds it (or gives up ).
I’ve taken a lot of photos of people on the train while commuting to and from work. I always used a 50mm or 28mm prime lens on an old Pentax MX SLR. I never asked permission, I just took out the camera, adjusted the focus to the approximate distance and then looked through the camera and snapped the shot (this took me less than 20s). My point is, I was doing this in front of the subject as it was the most natural thing for me to do (while it wasn’t always the case). The person I took a photo of never really felt uncomfortable during the shot, because I seemed not to be feeling uncomfortable either (while I sometimes was). Other people around us saw me taking a picture and none of them ever said anything during the 4 years of this project.
I admit, this is also related to the social habits of my country.

So in short: keep it natural like taking pictures out of strangers is your second nature.
People are getting used to the fact being photographed all the time (mobile phones with 5M cameras and digital point and shoots…) so if you’re behaving awkward and stressed so will they.

The other part in this discussion is the ethical and legal part.
Getting consent from a stranger to publish the photo is all but easy and to my personal opinion unnecessary if you’re not compromising the subject (someone doing something illegal, or throwing up…) or if they clearly steer their faces away from you. I think your own common sense is a good guide here. If you’re up close (using wide angles or small prime) they will have spotted you or at least someone else did. So, to my opinion, legally not a big issue as long you keep it decent and ‘artistic’ (which is always subjective). I never heard of anyone filing a lawsuit against an SP because he published a photo on a website or in a book/magazine. If the photo clearly shows the subject is on public ground (street, park, etc) and it’s not offending whatsoever, no judge is going to rule against the photographer.

Ethics differ from each person and society and culture. In a big city people don’t bother much and no one will come and tell you to be so decent to ask first permission to take a photo. In small towns this is a different game. And older people may have different standards then young people about taking pictures out of someone.

I’m an avid street shooter and love taking street portraits. I also love shooting from the hip and have gotten quite good at it. One approach I take it to simply ask people for their photo. If they agree I move them into good light and then have them look away so the shot seems more candid and natural. I also pay homeless people for their photos, which is a good way to practice.

It has always been daunting for me to take photographs on the street. Looking at your photos, it seems being a fearless street photography enthusiast can be rewarding! Let me build my courage gradually. Thanks for the motivating photos.