Go For It

05/01/2023 02:24 AM By Lisa Anderson
The Arts
Jessi Miller
Jessi Miller
Story by Taylor Strickland • Photo by Joshua Jacobs

Go For It

Painter & Entrepreneur Sells with Engaging Stories

“I consider myself a child of the world,” says Jessi Miller, graphic design artist and owner of Little Black Mask Media. “My parents were kind of hippies. We did a lot of traveling around.”

Jessi has lived all over the North American continent, including some parts of Hawaii, and the Caribbean. The constant travel made for a very exciting childhood, but it was one without connection. “I didn’t have a community throughout my life. It was just the whole world.”

In search of that community, Jessi and her family moved to Ocala some 20 years ago. “I enjoy growing roots and giving that to my kids. My children weren’t born here, but they were raised here.”

Despite her cultured upbringing, Jessi hasn’t found Ocala to be lacking in any way. “You could say it’s limited in size, but it’s so beautiful. I used to say, ‘There is a symphony, a museum, two Indian restaurants, a Thai restaurant, and it’s two hours from anything you might want to do that isn’t here. Anything else I can cope with.’”

Jessi lives a more stationary lifestyle now, but she still values her unconventional upbringing. “I love traveling. I think it’s the best education. It’s more valuable than school in many ways.”

Part of that education included fostering an environment that encouraged artistic talent. “Everyone is born an artist,” Jessi insists. “That doesn’t mean you’re good at it, but anyone can do it, even the people who say they only draw stick figures.”

However, adolescent Jessi was pretty sure she wasn’t just anyone. “We all have to take a humble pill at some point,” she says sheepishly. “In high school, I was a good art student, and I had some talent. I thought I was just going to go right to work and get a job in an ad agency. “ 

Jessi informed her art teacher, Ms. Dixon of Fort Lauderdale High School, about her grand plans to become a working artist once she graduated. “She said, ‘You don’t know what you’re talking about; you need to go to college.’ I’m so happy I took her advice.”

“I went to the Art Institute of Fort Lauderdale for advertising and design,” Jessi explains. “I learned how much I didn’t know.”

A Catalyst for Change

Initially, Jessi found the graphic design world bleak. “I was in ad agencies for about seven years out of college,” she recalls. “One day, I realized, ‘I’m just making things people throw away.’ I kind of felt like I had lost my soul.”

Magazine publishing helped Jessi develop a more positive outlook. “I felt more like I was telling stories again. There are still ads to make inside of a magazine and you’re still selling something, but you can do it with a story. It’s also a product people usually hold on to and engage with.”

The dissatisfaction Jessi felt working for ad agencies is tied to her personal philosophy regarding art and its purpose. “Art is the greatest catalyst for change in the world,” she claims. “Art helps us imbue concepts into our culture that we might be resistant to, but once we accept them, then they can become reality.”

Jessi points to the television show Will and Grace and its impact on the broader cultural acceptance of gay marriage. “There’s something to being entertained and being able to accept a concept passively. You get used to it and see it’s fine.”


Though art has remained a constant in Jessi’s life, she wasn’t always certain about a career in graphic design. “For a time, I thought I was going to be a traditional artist, but they starve before they’re successful. I went with the more practical choice.”

It was a choice made with some measure of regret. “I really love what I do, but I always tell young people that the biggest mistake I made was not having the confidence to really go for it,” Jessi laments. “When you’re young, you don’t really have responsibility, so you can make those sacrifices. If you think you will just do it on the side or later in life, it’s really hard, because it does take a lot of time. It’s not just creating the art but marketing it and marketing yourself.

“I love painting, and if that’s all I did, it would be awesome,” Jessi shares. “I paint bright, colorful paintings. When I paint people, I don’t like to do natural skin colors. Not that you won’t recognize who that person is, but I want people to relate to the human and what they’re doing in that painting versus their race or where they came from.”

Jessi wishes she could dedicate more time to her personal art, but with the demand for visual communication growing and the recent launch of Go52 Events–a charitable events website dedicated to hosting all the events Ocala has to offer–it seems like she is going to be busier than ever. “I guess it’s something I’ll be able to work on after I retire,” she laughs.
Learn More

Watch the full interview on YouTube. It airs May 19, 2023.
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