Here’s How I Took My Street Photography to the Next Level

New York City street photography is my passion. The ceaseless movement of people throughout Gotham provides infinite opportunities for capturing both commanding and subtle images. But I wanted my street photography to be unforgettable. I knew I needed to create a stronger connection with my subjects to make better images. I think I pulled it off.

Here’s how I did it.


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Eye Contact

Much of my winter was spent working in Grand Central Terminal, and in Hell’s Kitchen, creating content for a portfolio development program at B&H that I was attending. And yes, the more you get out and shoot, the better you will be. But as my street photography progressed, I noticed one theme that continued to run through my best images: eye contact.

Learn to be Honest with Yourself

Working the streets around Ninth Avenue, I realized that photos I had made, that I initially thought were going to be strong, often turned out tepid. Leaving me flat. In many instances, it was challenging to understand what the subject of the image was. When I was honest with myself, I could weed-out the weak shots quickly. Such honesty is humbling. There were days where I rushed home to look at my work, only to find that each image from the day’s shoot did not meet my new standards. See: crestfallen.

What Makes a Strong Image?

Conversely, there were times when the power of an image would hit me over the head like a sledgehammer. Certain pictures I made mesmerized me. Almost always each of these images contained a well defined subject that was looking right at me. There was a strong, passionate, connection. If there was no eye contact, the images that I felt worked possessed a haunting, almost surreal quality that evoked the loneliness of a Giorgio de Chirico painting–invoking art that influences you will make you a better photographer.

How to Get Eye Contact

The famous street photographer John Free says, “street photography is hard.” Indeed it is. Yet because of our access to cities, most of us believe all we have to do is walk down the street, shoot, and the rest will fall into place. I’ve learned it’s just the opposite. Making pictures of people simply strolling down the avenue, or of a sleeping homeless person is not going to compel any emotions of note, let alone create a connection between you and the subject. Most likely the converse, and your images will suffer for it.

My attempts to create that connection come down to ensuring that my intended subject knows I’m taking their picture. And at that ‘decisive moment,’ when they’re looking right at me, I press the shutter button. Provided I’ve done a good job of creating the setting of the image from the background forward, I’ve been walking away with lightning in a bottle much more often than before.

Give it a try, and be sure to let me know how it goes.


On Sunday, April 15, at 6 p.m., I’m hosting a Hell’s Kitchen and Times Square photo walk and workshop.  Want to learn to be a better street photographer? 
Just click below for details and tickets.