I didn't set out to define my entire approach with one image.

But looking back, that's exactly what happened.

It started at a kids' music camp in Oakland called Mr. D's Music School. Every summer they bring in professionals to show the kids what they do. I thought it'd be fun to bring my portrait setup and let them try it—some pressing the shutter, others sitting in the hot seat.

The main thing I taught them: how to engage your subject to get a real expression.

When a girl named Eboni sat down in front of my lights, I positioned myself behind the camera with about 20 kids behind me. They all started screaming, shouting, doing whatever they could to make her laugh. And she did—this huge, open-mouthed smile with pure joy radiating off her face.

I didn't fully realize what I'd captured until I got home and saw it on my big screen. The energy was undeniable and it was resonant. I could feel it vibrating off the screen in a way I'd never experienced with my own work before.

I spoke with her mother, Taniya, and told her I'd shot something special. I wasn't sure where it would end up, but I knew it was going to matter. Naturally, she was skeptical at first because she didn't know me yet. Why was I so certain? But we met, I shared some more of my work. I explained what was just intuition at the time and she ultimately trusted me. She signed the model release and said she wanted to come along for whatever happened next.

What happened next: I entered the image in Oakland's HHREC Health Through Art competition. A challenge to create a two dementional piece of art that promoted mental health, positivity, empowerment. I used this image and the words "Live Pure Joy".

It won first place. Got printed on the back of 50 buses across Oakland and Alameda County. Circulated through government buildings and galleries for two years.

But the real win took me seven years to recognize.

That image was my first editorial character portrait. Before I had a name for it. Before I understood why it worked. Before I built my entire practice around the same principle.

It wasn't polished. It wasn't corporate. It was human a real human moment, curated with intention. The kind of image that doesn't just represent someone. It makes you want to meet them.

Taniya loved it so much she ended up booking a full session for herself and Eboni , who was pursuing acting at the time. That was just the beginning of our friendship. They've since moved away, but we still talk on the phone. Seven years later, there's still a bond built around that one photograph.

"Live Pure Joy" was proof of concept before I knew what I was proving.

Brian DeSimone is an executive and editorial portrait photographer based in Oakland, California. With a background in hospitality and over two decades behind the camera, he's photographed hundreds of founders, C-suite executives, and creative teams throughout San Francisco, Silicon Valley, and the Bay Area. His specialty: directing people who aren't used to being directed, and making it look natural. Corporate portraits, teams and executive headshots that are polished enough for the boardroom, human enough to be remembered.