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Spreading Whimsy Around like Confetti / TWENTY SEVEN

PHOTOGRAPHY BY JORDAN RANDALL

Lakeland native Jenna O’Brien has turned a creative outlet into a business focused on spreading awareness about mental health and positivity in the community and beyond.

From selling products at local markets to owning her own brick and mortar, Twenty Seven owner, Jenna O’Brien, has taken Lakeland by storm with her whimsical illustrations and retro style, making our city a little brighter. “It has grown faster than I thought or dreamed,” she says.

When O’Brien started Twenty Seven in 2017, she had yet to discover the impact that her art was going to have on her life and the community. Going from creating art as a way to feel mentally healthy to selling her illustrations and creating a business focused on mental health was not something she had expected. The early stages of Twenty Seven consisted of four or five months of selling wall hangings, magnets, and a variety of bits and bobs at local markets. It wasn’t until O’Brien attended a class at Catapult that she considered selling her illustrations, which has since become the heart of the business.

Over the course of the last two years, Twenty Seven has expanded in Lakeland as well as online. When the space that previously housed Lakeland BBQ Company opened, O’Brien decided to get the building as a permanent location for the business, teaming with Benjamin Vickers, owner of Honeycomb Bread, in the process. The only issue was that they needed money to secure the space and get the storefront up and running.

The two business owners launched a Kickstarter campaign, an all-or-nothing crowdfunding platform for creators. Due to the exponential success of the two local businesses, they were able to raise over $12,000 in less than five months with the support of Lakelanders and people from out of state as well. “It has grown, like I don’t understand. I think where I am right now is where I hoped I would be when I was like 40,” says O’Brien.

Twenty Seven has accumulated a substantial online following, giving O’Brien the platform to not only share her illustrations, but to also be able to share her story. She has premenstrual dysphoric disorder, a mood disorder that causes severe irritability, depression, or anxiety. Due
to the lack of information and clarity about PMDD, many women don’t typically seek treatment or are misdiagnosed.

After launching a Kickstarter to fund the project, Twenty Sevenwas able to launch their brick-and-mortar store in the building that previously housed Lakeland BBQ Company this past year.

However, O’Brien’s transparency with her own experience has helped to shed light on
the disorder. “I’ve gotten a lot of messages throughout the last three years of people saying they went to see a doctor and figured out they had PMDD. It’s just kind of like a light-bulb moment for people because I’m being honest about it.”

“It has grown, like I don’t understand. I think where I am right now is where I hoped I would be when I was like 40.”

Although O’Brien created the foundation of Twenty Seven, it would not have been possible without her dedicated support system. Her husband, Connor, has been by her side since the beginning of Twenty Seven, carrying her stuff to every market. O’Brien’s best friend, Shelby Martin, attended most markets with her. And Scout Hunt, to this day, is O’Brien’s one and only photographer. Not to mention, a number of other local business owners have encouraged her throughout this journey. Most notably is Sarah Kent, owner of Penny Made, who was the first person to buy anything from O’Brien. Kent now creates the whimsical window displays in Twenty Seven’s storefront.

Twenty Seven has accumulated a substantial online following, giving O’Brien the platform to not only share her illustrations but her mental-health journey.
The early stages of Twenty Seven consisted of four or five months of selling wall hangings, magnets, and other items at local markets. Jenna O’Brien decided to start selling her illustrations, which has since become the heart of her business, after attending a class at Catapult.

Twenty Seven has become a staple within the community, spreading whimsy around like confetti (both literally and figuratively). Being a business owner has allowed O’Brien to share her illustrations to connect with many people. The biggest takeaway, however, is that none of it would have happened without her taking the chance to do it, which should serve a lesson to other aspiring creators.

As O’Brien says, “I think the best advice I can give is just to do it. Even if you’re scared or even if you don’t have it all figured out, just say, ‘OK, I’m going to try.’”

TWENTY SEVEN
213 E. Bay Street
Lakeland, FL 33803
twentysevenlkld.com