Havana Diaries- Lesson 13: Doors and Windows: A Photographer’s Obsession

It should come as no surprise that doors and windows have long fascinated photographers. Duh. I mean, who hasn’t been drawn to the vibrant patina of a well-worn door or the symmetry of a neatly framed window? Early in my career, I thought my obsession with them was unique, even special. Man, was I wrong. The truth? It’s the obsession of tens of thousands of photographers worldwide.

So, what is it about doors and windows that keeps us coming back? Simplicity? Geometry? Creativity? Probably a bit of all the above. But, as I’ve come to understand over the years, it goes deeper than that.

Doors and windows aren’t just subjects—they’re symbols. They represent life’s transitions: beginnings, endings, opportunities, and closures. As photographers, we’re inherently drawn to stories, and few things tell a story quite as powerfully as an old door with peeling paint or a window partially veiled by tattered lace curtains.

When I photograph a door, I often wonder who has walked through it. Who built it? Who locked it? Who opened it to possibility, or slammed it shut on pain? It’s the same with windows. They offer a glimpse—a suggestion—of what lies inside, or beyond. Sometimes, they’re just reflections, bouncing back the world outside.

I remember a particular trip to Regla, Cuba—a township just a hop, skip, and ferry ride from Havana. I only had a few hours there, but what a few hours they were. Regla felt like shelter from the storm. Life there unfolded quietly, yet vibrantly. The doors and windows in that small township were alive with stories.

There was a faded turquoise door that caught my eye. It was perfectly imperfect, framed by crumbling stucco walls. I couldn’t help but see it as a metaphor for resilience—its surface weathered by years of storms, yet still standing strong.

Nearby, I found a window, slightly ajar. Behind it hung a curtain embroidered with flowers, its edges frayed. Through the gap, I caught a fleeting glimpse of a woman sitting at a table, her face partially obscured by shadow. The scene felt deeply intimate, yet universal. How many lives have unfolded behind similar windows? How many stories will never be told?

Photographing doors and windows is, in many ways, a mirror of the photographer’s journey. We’re constantly searching—for light, for meaning, for a moment that feels like truth. Doors and windows are prompts, urging us to look closer, to step through, or to peer beyond. They challenge us to confront our own emotions—some resolved, some not so resolved.

For me, the pull is irresistible. It’s not just about the visual appeal, though that certainly helps. It’s about connection—to place, to people, to possibility.

And maybe that’s why we love them so much. They remind us that the world is full of thresholds, waiting to be crossed. Some open to new beginnings, some close on chapters we’ve left behind. As photographers, we’re the storytellers standing in the doorway, capturing the view both ways.

Click.

Jack.

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Jack Hollingsworth
Photographer