Tom.

I just finished three days of hosting meet-ups and mixers and workshops, oh my. I had the most amazing experience, which will get a full write-up tomorrow. But to start off with, let me publicly reveal my big, secret assignment: I challenged the workshop attendees to take portraits of a stranger … and, if possible, to take those portraits in their homes. This is an intensely challenging assignment for most people, and it’s one that I encourage photographers who are very interested in the documenting of people’s lives to try on their own. The lessons everyone draws are unique, but you learn a lot about making others comfortable, about being comfortable in your own skin as a photographer, about subject trust, and all of these skills that are very, very hard to teach in a one-day workshop.

I didn’t want to assign the attendees anything I wasn’t willing to do myself, so I went out and found a stranger of my own. Meet Tom. Unfortunately, Tom lives way, WAY out in Queens, and with the workshop planning I simply didn’t have time to go out there, so I photographed him at my office. But as soon as we started talking about the project, I knew I had to shoot him.

Tom saw this shoot as an opportunity to learn a bit more about himself. We got quite personal in our discussions and I won’t share them here, but he is 21 and sees himself in the middle of some major life transitions that have him searching for questions like “What’s next?” “What do I even want?” and “Who am I, anyway?” Trust me, these are questions that we keep asking ourselves, or should. But he also has a strong sense of whimsy — his role model, in ways, is Calvin from “Calvin and Hobbes.” So I wanted to get at that a bit with these portraits. We started indoors, using a mix of warm video light and cool window light to visualize these transitions and melancholy, but as we got more comfortable I had him change into one of his favorite shirts, a colorful Simpsons shirt he happened to have with him, and we headed out for some portraits with a lighter feel.

The biggest lesson of this assignment? We all want our stories told. Make people comfortable, and they will share theirs. Thank you, Tom, for sharing yours with me.

(The skyline is reflected in his glasses on purpose)