The Daunting Challenge of Street Photography

I love looking at good street photography. Skilled street photographers can create an image that tells a story and captures some real emotional content. Great street photographers are natural observers of the world around them and have a knack for knowing exactly when and where to take a photo that effectively documents what they see. It takes instinct, boldness, vision, and an innate feel for the flow and rhythm of city life. An understanding of light comes into play as well as patience and persistence. There is no doubt that luck plays a role but it is amazing how “lucky” the best street photographer get over and over again. No one is that lucky. Unlike landscape photographers, street photographers can’t go out with their camera with a specific shot in mind. They can only be on the street, keep their eyes open and hope to be inspired by a scene or a person. 

My favorite street photographers are Garry Winogrand, Robert Frank, Elliot Erwitt and, of course, Henri Cartier-Bresson. Just Google these names and you will get lost in a  digital rabbit hole of amazing images. To get a sense of what it takes to be a street photographer you should check out “Everybody Street” (free on YouTube) which features such great as Erwitt, Jill Freedman, Bruce Gilden, Mary Ellen Mark and Joel Meyerowitz. As Freedman comments in the film, photography is a tool that is able to “stop time itself.”

I would love to create amazing street photography but I find this genre to be very challenging. While I am patient and persistent, I am probably too inhibited and timid to make the kind of images the world-renowned photographers have been able to. Their fearlessness with their camera allows them to truly inject themselves into the flow of humanity that we see in every city. They seem quite comfortable in situations that make most people quite uncomfortable. 

Despite my limitations, I have tried to do street photography. Fortunately, I live close to New York City, arguably one of the best places to shoot even though the visual stimuli that bombards us as we walk the streets can be overwhelming at times. Occasionally, I have been bold enough to  position myself in the right spot and capture something interesting. At other times I have “cheated” by using a long lens to photograph scenes from a distance which is a little less scary but generally not as effective. 

Commuting through Grand Central Terminal for 25 years put me in a great spot to shoot and it is still a spot I love spending time in with my camera. Here are some of my favorites from Grand Central that capture both the hustle and bustle of the place as well as the loneliness of some that commute through the terminal. 

Having lived and worked in New York for 30 years, I have come to appreciate the “New York attitude”, something that is easy to see but quite hard to document with a camera. Here are several images that at least partly capture the New York sensibility. The image on the left occurred when I was practicing my panning technique one afternoon. The biker’s “reaction” was classic New York and made the photo. During my walk to work from Grand Central, I often passed these two guys in front of the New York Public Library and, after about a month, I worked up enough nerve to ask them if I could take their picture. “Why the f___ do you want to do that?” was the perfect New York response. Still, they agreed and I captured the middle image below. 

On a rare occasion, I will be bold enough to ask a person if I can take their portrait. So far, no one has said no and these are my two favorite street portraits. I need to try more. 

Central Park is a fantastic place to try street photography especially during the summer when the park is packed with a diverse group of people — at least pre-COVID. 

Precipitation can really add to the mood of a street photograph. The big challenge is protecting your camera and lens from getting wet. For these images, I juggled holding my own umbrella while shooting — a frustrating task. By the way, in the image with the blue umbrellas, I did not alter the color of the umbrellas, I just desaturated the rest of the image. 

One challenge I have is that most people walking around New York are looking at their phone which, in my view, makes for an awful photo. In these images, I tried to find people that were actually connecting with each other rather than connecting a device in their hands. 

In a crowded city of 8.4 million people, it is always interesting to spot a lone person (or dog) on the street. It is a sign that with all the frenetic activity of the city, people can find solitude or — looked at more skeptically — loneliness.

There have been some situations where I have been attracted to a particular scene and just waited for someone to walk by, hoping I get lucky. My favorite image in this set is the upper left photo — I love how the smiling model seems to mocking the downtrodden pedestrian.

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