We discussed how your parents' role in education provided an opportunity to attend private school. What aspects of that experience made you feel like you didn’t quite fit in? How did stepping outside of that environment to encounter different walks of life in New York shape your sense of belonging and influence the themes you explore in your work?

I’m from Manhattan, born and raised in Greenwich Village, and it was an incredible experience in many ways. New York has this raw, unpredictable energy that exposes you to many different people, cultures, and experiences. You learn quickly how to navigate both physically and socially. It taught me about independence, resilience, and the value of observation. I was constantly encountering new perspectives, which helped shape my identity.

My parents were both educators, and they prioritized my brother’s and my education above all else. As a result, we attended private schools on the Upper East Side of Manhattan, a neighborhood as distant from our sensibilities as could be imagined. I found little to connect with in my school, or with the other students. It was a world of privilege and exclusion. I rejected that world, and when I graduated, it was as though the air had cleared for me, finally an escape.

The typical stories about people in New York that you see on TV and in movies don’t interest me. There are plenty of wealthy, powerful people here, and those are the stories the media loves to repeat. I push back against that narrative. The people I’m drawn to talk with, and photograph aren’t polished or powerful, but often they’re the ones who truly make up the backbone of the city.

In all my photography projects, I’m constantly drawn to photograph and connect with overlooked communities.

In our conversation, you mentioned that sitting down to intentionally brainstorm a concept for a new series isn’t a productive approach for you. Could you expand on how serendipity influences your creative process?

A huge part of my photographic process is relying on serendipity and the kindness of strangers. My projects would not exist without their generosity and openness of strangers. Some people I photograph lead inspiring lives, I learn from them. There's always an element of the unknown—it's impossible to predict what will unfold. If we end up talking for a while before I make any photos that’s fine, I enjoy the interaction. You never know what is going to happen, what they will share with you. It’s this intimate encounter.

There are other photographers who stage photos beautifully, but I rely on the found moment and encounter.

Sometimes, when I'm struggling to find a spark for a new project, I dive deep into the internet, exploring various concepts and seeing if other photographers have already tackled them. Often, it feels like a dead end. I waste too much time agonizing over ideas, too much time glued to a screen. For me, the intentional brainstorming of a concept is rarely productive—it often just leaves me feeling stuck and like I'm failing for not coming up with something new.

But when I go out with my camera, it’s a different story. Serendipity takes the lead. The act of walking, photographing, and meeting people is where the ideas begin to flow. One thing leads to another, and before I know it, I’m immersed in something unexpected.

We shared our experiences of navigating the world as female photographers. While I hesitate to frame it as a limitation, since I see many advantages to it, could you share moments where your identity has empowered you? Additionally, are there times when it has made you feel unsafe or hindered your ability to pursue a photograph?

In many ways, being a female photographer is an asset. People who are usually guarded seem more willing to open up to me than to a male photographer, perhaps because I’m not seen as a threat. Yet, there’s a part of me that envies my male counterparts. They don’t have to carry the weight of concern when stepping into a stranger’s home.

For intimacy to take root in my work, I spend a lot of time with the people I photograph. Much of this unfolds in their homes, on their porches, places where they might feel most themselves. The trust that emerges between us never fails to move me. People share stories about themselves in ways that are so vulnerable. This exchange always feels like a gift.

I seek out connections with strangers. I believe everyone has a story to tell and when I'm having a serendipitous encounter with a stranger it's almost as if the camera becomes secondary. What's prominent in my mind is the experience I'm having with the person. I love to listen to them share their stories, watch them move, and take in their grace. My desire to connect with strangers drives all my work. The fact that the person is a stranger means you both come to each other with no obligations, no past. The past can be like a long shadow that follows you around, whether you like it to or not.

I recently had an experience that left me unsettled, a reminder of the subtle line women walk in this world. I had been photographing a man with whom I’d grown comfortable, spending hours together, sharing conversations. He’d always been flirtatious—a behavior I’m accustomed to, one I usually deflect with light-hearted banter, a way to keep things in balance. But this time, the flirtation crossed into something more intense, it felt different. "Someday," he said, "I’m gonna get you." There was a shift in the dynamic, and just like that, I knew I couldn’t return to photograph him.

Each time I set out to photograph strangers, I feel a familiar knot in my stomach. Will they say yes? Will they give me the space to linger, to ask questions? It’s a nervousness I’ve come to expect, but it never quite fades. But how can I ask others to expose themselves in front of my camera if I am not also willing to stand there, vulnerable and nervous, alongside them?

Many of your projects have been derived from your dedication to a long term commitment of deepening relationships with those you photograph. How has your recent project documenting the carnival altered your process and what have you learned in doing so?

My work on carnivals feels like a departure from my past projects, where I’ve focused on getting close to people and communities. Yet, there’s a thread of continuity—I’ve been returning to photograph these carnivals in upstate New York since 2021, seeking out the same workers I've spoken to and photographed before. Some I find, others have moved on, no longer working at the fairs.

With this project, my interactions are much shorter, so I must build trust and get them to agree to a portrait much more quickly. There’s also a strong element of street photography in this work, where I’m responding in the moment to the frenetic energy of the scenes around me at the fairs.

The carnival, in its transient nature, offers a kind of reinvention, a space where the past is no longer a weight.

I’ve heard countless stories from fair workers. One man, who has been with the same carnival since 1988, told me how he got into a fight, was stabbed, and yet he was the one who ended up in prison for four years. When he was released, still in his early twenties, he saw the familiar pull of old habits—drugs, crime—dragging him back into a life that no longer fit. Then the carnival came to town, bringing with it a sense of possibility—a chance to start fresh.

On another occasion I met an insightful and funny carnival worker while he was working the darts and balloon game. Going by the nickname ‘Soup’ he told me about his life, past regrets, and the many hours spent working at the fairgrounds. He told me that working at the carnival is a refuge for those who don’t quite fit in "out there," as he gestured toward the world beyond the tents. Over time, he had become a keen observer of both humans and nature. “I watch people,” he said, “I see interactions and behaviors, I watch the moon rise and fall over the trees…I see beauty.”

When we listen to others, their stories stay with us. Where did your interest in learning from others begin?

I used to hitchhike a lot around the United States and Europe with my boyfriend at the time. One part of the "code" was that, in exchange for a ride, you’d keep the driver company—especially during long stretches of road, making sure they stayed awake. But something magical would often happen, particularly at night, when the road had this rhythmic, almost meditative quality. After a lot of conversation and me asking plenty of questions, the driver would suddenly become incredibly open, sharing brutally honest stories about their life. It always felt so special, like I was having this rare encounter with a perfect stranger. The fact that someone would open up to me as if I were a priest was remarkable. And then, we’d reach our destination, the driver would drop us off, and that would be it—no more contact. For that brief moment, though, there was this deep, intimate connection. I love that.

Now, as a photographer, I still get to have those amazing encounters with strangers. People tend to be guarded, but I enjoy recreating that experience of breaking down those walls and getting them to open up. The people I seek out to photograph are far from polished; they’re outsiders, often living in remote places. Their outsider status resonates with my own feelings of alienation, and through photography, I’m able to satisfy my need to connect with others.

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Maureen Drennan