Practical Whimsy

©Gilmar Smith

Every photographer receives the same sound advice: define your style, find your niche, stand out in the crowd. But getting to that promised land can be a long and winding journey, and if you’re doing it right, the learning and experimentation—and rule breaking—never ends, according to creative and conceptual portrait photographer Gilmar Smith.

Smith’s first experience with a camera was straight from a movie, she says, where the character opens a box, and light pours out. “It was like something magical.” The camera was her ex-husband’s; he’d used it for a bit but then left it in a corner. Her marriage had ended, and her son had just been diagnosed with autism. “I was navigating all these changes in this difficult time, and the camera somehow became my emotional outlet,” she says. “It was fantastic because it opened the door to so much creativity that I’ve always had.”

©Gilmar Smith

Smith experimented with anything and everything—long exposures, macro photography—and eventually settled into a gig as a photographer for a motorsports team. She loved the excitement of the sometimes 24-hour events but realized over time that it wasn’t the cars that revved her engine. It was the people. “I wanted to take pictures of the team members. I wanted to take pictures of the drivers,” she says. She listened to her heart and pivoted to portraiture.


As she trained herself in portrait lighting, Smith found it increasingly difficult to persuade family members and friends to sit as her subjects. She delved into self-portraiture as a solution, and this became pivotal for her technical development and creativity. “I was the only person who was only available for myself,” she says. “I was the only person who was patient enough to sit there forever until my light was right, until my settings were right, until the pose was right.” It was total creative control, with no one to complain that they didn’t like how their chin looked in a photo. “So that makes you tap into different things,” she says.

At about the same time, she made a breakthrough with her son who, because of his condition, vacated the room as soon as the camera appeared. Instead of simply pointing the camera at him, she began by building a story with him first. “Once upon a time we were …” she would begin, and he would respond with something like “in the mountains.” She’d continue, “ … and there was a character called …” to which he’d fill in the blank. And on and on. Soon the two of them had conceived of a story that he was happy to act out in front of the camera. She would then use Photoshop to build out the background they’d imagined together.

©Gilmar Smith
©Gilmar Smith
©Gilmar Smith

“He was completely into the project,” she says. “We started creating these composites together based on his ideas, based on things that he loved. And he was such a big part in creating the whole thing, from the picture to the story and the elements that we have in Photoshop. So, to me, after that first one I did, I was like, This is it. This is what I love doing the most because it wasn’t just a picture of anything. It was a reflection of the person that he was at that very specific age, at that very specific moment.”

The experimentation she did with self-portraits and composites ultimately molded her distinctive style and whimsical approach to portraiture. “What if, whenever I create anything that I create, I bring that little magic that we all have inside—that is our funny side, our inner child, our creativity, and all of that?” she thought.

Even when she’s working with a client for personal branding photos, she taps into that whimsy, incorporating the client’s personality, story, vibrancy, and her own imaginative ideas into the compositions. “I just always take my time to make that connection,” she says. “And to me that’s very important and that’s why I photograph people because I love feeling that connection.”

©Gilmar Smith
©Gilmar Smith

Though personal branding photography now makes up about 60% of Smith’s income, her initial foray into that specialty wasn’t a business decision. One year after the late-year family portrait rush, she was looking for another project to fill her downtime after the December holidays. “I was like, OK, I’m going to start doing personal branding photography,” she explains. “But I did it just as a test and the funny thing is that it just made a boom, and I didn’t really market it that much.” She simply offered the sessions on Facebook to people she already knew, and referrals rolled in via word of mouth.

Smith is based in Orlando, Florida, a locale brimming with real estate agents, who have become her primary client base for personal branding photography. Instead of doing humdrum headshot sessions that wouldn’t allow her to flex her creativity, Smith veered toward making images with a vibrant, commercial look that tell a unique story about the subject, harkening back to her self-portraits and photos of her own kids.

Her clients ate it up. “That’s when it started working for me and when people started chasing me because it was different and it was colorful,” she says. Real estate agents were particularly interested in her take since many are looking for ways stand out in a crowded marketplace. And a lot of them have bold personalities. “So many of them hate each other,” she laughs. “It’s funny.” They’ll come to her for a session and point-blank tell her they’re looking to top another agent’s images. “I love them all, but I love the kick of having to step up every time and do something completely different because, obviously, they don’t want something similar to their competitors.”

Since the photos provide a creative take on the subject’s personality, it’s important she gets to know them prior to the session. First, she shows them her Pinterest boards to get a sense of their tastes. She then engages them in a long phone conversation, getting to know them and asking what they enjoy outside of work. If she knows their hobbies, she may be able to work that into a photo. A finance guy who bicycles might want to bring in his bike for the session, for example. The important thing is to get a good read on the client’s personality and build a set of images that speak to it. She doesn’t want to push an introvert into super silly photos if that’s not his personality, as that would be misleading for his clients. But when a client with a big personality told her she’s always on the phone, she suggested photos where the client held a banana up to her ear as if she was talking into it.

Creativity is key—it’s her brand. She loves seeing the reactions to her photos on social media. “I’ve seen that the more creative the pictures are, the more colorful they are, the more impact they have on their audience,” she says. “So that’s what I always try to incorporate into my photography because it’s my style and it makes people stop and look for a while because it’s not the same thing over and over again.”

Amanda Arnold is a senior editor.