by SC Reporter Emilie Alfino
The Bailey family is iconic on Sanibel, and its legacy is safe in the hands of Francis Bailey’s granddaughter Calli Johnson. The family has been serving the community since 1899, in many different ways, not the least of which, of course, was Bailey’s General Store.
“I look at it as an honor to be able to fulfill that need for people, but also that makes it really hard to not be open right now, because we can’t do that for people,” Calli said. “We can do that in a limited fashion at the Island Store on Captiva, but it’s not the same thing as being able to walk into the big brown box, as we affectionately call the general store, the way everybody used to be able to do.”
Calli started working at the store summers while she was in college at the University of Florida. She was earning a degree in psychology and a master’s in mental health counseling. “When I realized I was going to stay with the store, I went back to school and got my MBA,” she explained. “While psychology and mental health counseling aren’t directly relevant to working at a grocery store, it certainly helps you understand people a little bit better. We have a huge variety of customers, and just being able to listen when someone is upset, I find it to be helpful.”
For a couple of summers, Calli bagged groceries, and between her master’s degrees she started working full-time at the store, filling in gaps in every department so she could learn how those departments worked. She started at the coffee bar because that’s where staff was needed. “Then we realized that would be a good thing for me to do, to help in every department. Then I would get more responsibility.”
Among other duties, Calli became the wine steward. “Nobody else wanted to do the wine, if you can believe that,” she said. “I said, ‘I’ve had some wine in college, I’ll give it a go.’” It turned out to be a good fit. “There’s always something new to learn about wine. Wine is ever-changing, and it’s important to me personally to always be learning something and evolving. That’s important for the store, too. We want to maintain our historic charm, but we also want to meet the needs of the modern customer, too.”
While she never had a specific title at the store, she considers herself the “big picture” person, looking around the store, finding the problems and figuring out how to fix them. They just got the keys for the new Rabbit Road store, A Bit of Bailey’s, and Calli is excited to see that space come to fruition. “I’ll probably be working on that for a while,” she said. “I pretty much do whatever needs to be done.”
Since Hurricane Ian, Calli, like many people, has gotten to learn more about construction than she ever thought she would. Now she spends her time planning as well as supporting operations at the Island Store on Captiva, where her mother Mead is spending every day making sure everything is running smoothly.
Calli wants to continue her work with the store. “When I was younger, my parents didn’t plan on me being involved in the business, it just kind of happened. So nobody ever primed me that I should be planning on having a life in a grocery store,” she said. “That was a big shift in perspective for me, coming back, giving it a try, and then realizing I enjoy it, this is a pretty good fit for me. I think a lot of people my age have been told if you’re smart you can do anything you want in life. But I never thought groceries would be what I wanted to do.”
While the store didn’t seem like her possible future as a young person, she held off making a decision. “I would be getting yelled at by somebody checking out because I put their cilantro in the bag wrong,” she said. “That doesn’t inspire you to say this is what I want to do with my life. But I see the value in carrying on the legacy. And that’s what moves me forward on days when someone yells at me for how I bagged their cilantro.”
“After coming back after school and working at the store, I told myself if I hated it, I would be honest with my parents and say, it isn’t for me. But I really enjoyed myself,” Calli said. “Good days and bad days, like every job. But it became obvious to me that it’s an honor to be able to carry on a legacy that many people don’t have in their lives. There are very few fourth-generation Floridians. Especially from the 1800s.”
Calli actually has two full-time jobs: with her family at Bailey’s, and at Florida Gulf Coast University where she teaches students the certification they need to do research underwater. Her official title is Dive Safety Officer, making sure everyone meets the standard requirements and helping students with underwater research.
“It was something I was interested in at the University of Florida, and I started teaching in that program in grad school for beer money. Then when I came down here, I missed teaching so much,” Calli said. “There’s nothing like seeing the joy of someone who is overcoming a challenge – especially underwater.” Wanting to continue her work from UF on her return to Sanibel was perfect timing because FGCU had just started its program.
“I need to be on the FGCU campus a couple of times a week. Some days or weeks there’s not a lot going on, but other times I’ll be on a research ship out of town,” Calli explained. “It’s flexible, just like my job at Bailey’s, so I’m able to bring the two together. Do I enjoy staying up nights grading? No. But that’s part of it.”
Calli is on the board of the Sanibel & Captiva Islands Chamber of Commerce and served as the youngest board chair in 2022 – the year of Ian. That storm changed her responsibilities a lot, she said. “The Chamber is very close to my heart. I’ve had the opportunity to grow a lot, and I’m so grateful for the people who gave me that opportunity.” Calli said the job of a chair in a well-run organization is to be supportive of the president and CEO, and she called John Lai a strong leader. “I gave my opinions and feedback, but really it was my pleasure – and now as past board chair it is also my pleasure – to be supportive of the objectives of the Chamber.”
Calli is just finishing her role in the Preserving Paradise Leadership Program, which is an effort by the Chamber, the Sanibel-Captiva Conservation Foundation, the Everglades Foundation, and Captains for Clean Water. “Those organizations came together and said it’s important for us to be able to inform business leaders in our area why literally preserving paradise is important and to give them the tools to advocate for this area,” Calli explained. That could be advocacy with local, state, and federal governments, but it also could be advocating on behalf of the community with customers. “We have people that visit us from all over the world,” Calli said, “and water quality is very complex, and what’s said in public is often not what is happening behind closed doors.” The goal was making sure that business leaders in Southwest Florida have the education and understanding of how everything works to ensure people advocate in the right direction. The focus was how all systems in South Florida integrate. Graduation from that program is coming up this month.
Calli also took part in the Charitable Foundation of the Islands’ Leadership Program in 2022. That program takes people who are either new to the community or are interested in being involved but not sure the best way to do it yet. The program educates those people so they can learn where they fit best. “I always expect to learn something in things like that, but I was amazed how much I learned,” she said. The program is focused on Sanibel and Captiva.
Did Calli make a conscious decision to reach out and become involved in the community? “Well, no,” she laughed. “It’s what we do, right? My dad set that example, my grandfather set that example, I’m sure his father set that example for him,” she said. “I really didn’t think about it and frankly, to be so young in a community like this where there are incredibly impressive people who have retired from being heads of companies, I’m always so flattered to be invited to do anything in a role similar to that.”
Calli attributes her confidence to the fact that her parents always told her she could do whatever she wanted. “If you don’t believe in yourself, nobody else is going to believe in you,” she said. “Sometimes it’s not how I’m feeling on the inside, but you have to set a good example for people. I’m fortunate to be in a mentor role, especially with my scuba students, so I have to put that out into the atmosphere, even if I don’t feel that way when I wake up in the morning.”
Calli married Evan duPont October 19 at the Old Bailey Store in the Sanibel Historical Museum & Village. “We’ve been together for a very long time. When we got engaged, I said we’ve got to go ahead and get married before anything else bad happens,” Calli said. “Then there was Helene and Milton, two weeks away from what’s supposed to be our wedding.” The Monday before the wedding, they told everybody, “It’s on. We understand if you can’t come now, but we’d love to have you, we’re having a party, see you there.”
They had their reception at the Captiva Yacht Club. A honeymoon is on hold while they make repairs to their house from Hurricane Milton.
“Many people in the world don’t have any sort of historic legacy like we do. I feel very lucky that we have a special place to get married.” Calli’s brother Dane got married at the Bailey Homestead property. “It’s kind of a tradition that he started. I’m sure Bailie will think of a place that’s special, too, to our family and the island, whenever they’re ready.”
Calli plans to stay on Sanibel long-term. “I’m going to be here as long as I can, because there’s nowhere else in the world like it.”