Jenna O’Brien

It’s often said that being a “creative,” whether that’s musically, artistically with writing or drawing, or any other form of art, is just a hobby. And when a high school student who has a knack for art considers the prospect of making it their career, fears of it being an unsustainable and low paying “job” might stop them. But what if art was more than just a hobby and more people found ways to make their craft into a profitable way of living? These LCS graduates are proof that you can take a childhood passion and make it into a a career. See how they did it and be inspired.


Jenna O’Brien began LCS in the 9th grade and graduated in 2016. Raised in the Brandon area, she commuted 45 minutes one way for all of high school. After graduation, she attended Southeastern University and in 2019 graduated with a bachelor’s degree in communications. Since graduating, Jenna has lived in Lakeland with her husband Connor, who she met at LCS in 2014 during 6th period journalism class taught by Sue Gibson. 

“It was love at first sight,” Jenna recalls. 

Jenna and Connor are both creatives, carving out their own path, with Jenna’s love of design and Connor’s love of film. Lakeland was a perfect place to call home because it is accommodating for entrepreneurs and has a strong arts community. 

“We found a wonderful community of people that helped make our big dreams come true,” Jenna said. 

Jenna has influenced the community in numerous ways. One way is through her role as Creative Director of the RISE Institute and LCS’s Digital Media Specialist. Jenna credits these opportunities to Jennifer Canady who started the RISE Entrepreneurship a decade ago, when Jenna was a student. Through RISE, Jenna attended lunch-and-learn sessions with Publix graphic designers, which helped confirm her interest in marketing. 

“I believe our environments deeply impact how we feel and how we view the world,” she said, “And I feel it is my calling to use design to help people feel loved and known.” 

Jenna assisted in the development of the RISE curriculum and designed the RISE learning space. She intentionally implemented colors and textures that “make the collaborative space feel like home.” The RISE space has become a “positive part of their childhood memories,” and Jenna feels like she’s “succeeded in life” by being a part of that. 

Jenna has had an artistic eye ever since the 3rd grade. At the time, she was the designer and circulator of a newspaper called “Kids Weekly News.” Through designing the newspaper she was introduced to the computer software Word Art, which she said, “is not super different than what I love to do now!” 

At 21, she opened a storefront called Twenty-Seven, a paper goods, home decor, loose-leaf tea, and matcha bar which was her “labor of love.” Unfortunately, due to COVID, that dream was short lived. Jenna was devastated, but still grateful because it served as her start in the entrepreneurial world. “I loved the space and it became so many people’s favorite space,” she said. 

Although Jenna’s store closed, her heart for the community of Lakeland never dwindled. With hope for her artwork to “bring sunshine inside,” and to “echo hope and resiliency,” she partnered with Gospel Inc., a Christ-centered community that provides homes and work opportunities to the formerly homeless. Jenna met with future residents and designed unique houses for them based on their interests. She also painted a giant colorful wall of flowers, chickens and plants in their outside community dining area. Some residents have never felt a sense of “home,” until coming to the Village, so for Jenna, it was a “privilege to create a safe space for someone to land.” 

Jenna’s other creative interests can be seen on Instagram @jennaisfeeling, where she posts about colored dots with descriptions inspired by songs, restaurants and memories. 

“In 2017, it started as a creative exercise for me to explore the relationship between design and feeling,” she said, “but since then, it’s become a following of color lovers.” The color dots also inspired her products and tea names at Colory Theory Tea, a company she founded three years ago.

Since Jenna joined the LCS staff, she’s followed in her teacher’s footsteps and has encouraged students to explore their interests. 

“What do you think God made YOU to do?” she asks her students, 

“If you have an inkling of an idea, get up and do it every day,” she said.

 She expresses gratitude to teachers Kari Clever, Sue Gibson and Barb Moore who taught her Adobe programs and design essentials, as well as former Advancement Director, Steven Wilson, whose leadership inspired her to pursue communications and design. They played pivotal roles in helping her get to where she is today.