Our latest Headshots Matter StudioTalk features Warren Shepherd, a Toronto-based photographer whose path into portraiture is as unusual as it is inspiring. Before ever picking up a camera, Warren was a writer—one who built worlds on the page long before he began building them with light. That foundation in storytelling now shapes everything he does behind the lens.

Special thanks to Warren for his openness and insight — and for reminding us that creativity often finds its way through new chapters, not just new tools.

For those of you who enjoy a read in addition to a watch and listen, we’ve created a short blog excerpt below. [↓]

Please enjoy and feel free to comment with any questions.

Cheers, Dwayne.

From Writing to Photography

Warren’s love for storytelling goes back to childhood. As a self-described observer and “recovering introvert,” he grew up watching people closely—trying to understand why they do what they do. That instinct eventually led him to write fiction, including a science-fiction novel published after a life-changing accident. When his recovery forced him to rethink his career, he turned to photography as a new way to tell stories about real people instead of imagined ones.

“I was always watching, trying to figure out why people do the things they do. Now I get to translate that into images that say something true about who they are.”

That curiosity became the core of his photography. He taught himself through online mentors and hours of experimentation, gradually discovering how light could shape emotion. Each technical lesson fed back into his real interest—people, and how they show up in front of his camera.

Building Trust Through Conversation

For Warren, every portrait starts with listening. He sends clients a short questionnaire before each shoot to learn about their work, values, and sources of pride. It helps him understand their story before they ever step into the studio.

“I want to pull as much as I can from everything that makes them them. Even in corporate headshots, there’s a story worth telling—why they do what they do, what makes them feel fulfilled.”

During sessions, he talks to people about their lives, families, or work—anything but the shoot itself. That conversation loosens them up until the camera feels like a friend rather than a machine. He often captures his favourite frames in the transitions—those unposed moments when a subject forgets to perform.

Light, Emotion, and Control

Unlike many new photographers who start with natural light, Warren went straight to studio lighting. He saw it as a way to build a story rather than find one. By controlling light and shadow, he creates images that feel cinematic yet honest.

“The story’s in the eyes,” he said quietly during our conversation. “I want people to connect with the camera as if it’s their confidant. You don’t have to speak to tell the truth.”

That belief in emotional truth also guides how he helps nervous clients. He knows the camera can feel intimidating, so he keeps the energy calm and conversation steady. He calls this balance his “acting training for introverts”—stepping into a slightly bigger version of himself to set people at ease

Human Connection in a Digital Age

Warren is realistic about the rise of AI tools in photography, but he believes their limits reveal what makes the human side so essential. Artificial intelligence can replicate a look—but not the spark of connection between photographer and subject. He smiled when he imagined a future filled with “flat, boring, over veneered AI images,” then added with a laugh that he’d be “the crusty old guy in a bunker, the last photographer left to take a real portrait.”

For him, the heart of portraiture will always be conversation and curiosity. Whether he’s photographing actors, entrepreneurs, or everyday professionals, he looks for that fleeting moment when the camera disappears and the person emerges.

Still at the Beginning

Though he’s only been shooting portraits for a couple years, Warren talks about his career as “just the beginning.” He approaches each assignment with the focus of someone who knows time is precious—and that every photograph adds to a larger story about human connection.

“What you have to learn,” he said at the end of our talk, “is how to connect to another human being. It’s that simple. It’s not about you—it’s about them.”

Warren’s words capture what so many photographers in our community believe but rarely say aloud: that great portraiture is less about technique and more about trust. In Warren Shepherd’s work, you can see that trust in every quiet, steady frame!

You can view Warren’s work at: www.warrenshepherdphotography.com or follow him on Instagram at: @warren_shepherd_photography

Please also take a moment to subscribe to Warren’s YouTube’s channel at: @warrenshepherdphotography and I recommend checking out these specific videos:

My Origin Story | My Secret To Defeating A.I. | My Secret to Beating Impostor Syndrome | The Introvert’s Guide To Portrait Photography

StudioTalk