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External and Legislative Affairs Manager - Pinellas County Sheriff's Office

Posted By Megan Holmes


Joanna Cheshire is about impact and intention. The Tampa Bay native has dedicated her career to public service, and her spare time to deep work with organizations and people she believes in. Truly a bridge-crosser, Cheshire makes the most out of life in Tampa Bay. She lives in South Tampa, commutes to work at the Pinellas County Sheriff's office, and spends many weekends jet-setting around the bay and beyond with her rescue dog, Pina.

Years in St. Pete

I live in a suburb of St. Pete called South Tampa. I’ve been in South Tampa for 12 years, I love St. Pete, I have a history here. I actually started my career in St. Pete. I was a legislative aide for two years for Rep. Bill Heller and our office was on Central. There really wasn’t much past Tropicana Field so it looks like a lot different now than it did then.

Organizations involved in

I am currently on the board of Leadership Pinellas as well as Suncoast Tiger Bay, I’m involved with Girls Rock Camp St. Pete, I recently became a literacy tutor with the Hillsborough Literacy Council doing one-on-one adult basic English, and whenever I can fit it in I love to volunteer with Heartwood Preserve, which is a conservation cemetery in Trinity. They do all green burials, which is a pretty neat concept and they’re one of two conservation cemeteries in Florida.

What gets you out of bed every day?

The short answer is Pina, my rescue chihuahua. She’s just amazing and really brightens up my mornings. But really, possibility and opportunity. Every day is a new start. I work for the sheriff’s office because I love public sector work. I have graduate studies in public administration, my undergrad was in political science so I knew that I always wanted to dedicate my career in working for public organizations, never to make a profit for someone. I wanted to work with the community and make our community a great place to live no matter how small my role is in that. Every morning I’m energized to see what the day holds, I have an awesome team that I manage. They’re so wonderful and they’re professionals in their field. I learn from them and hopefully I’m able to impart some wisdom to them with my experience. Every day is different in my line of work. Working in public affairs, I take care of community partnerships for the Sheriff’s office, legislative affairs, marketing and communication.

Why St. Pete?

St. Pete is such a special community to me. You can’t even compare it to other areas with how much you have that sense of community here. The inclusivity, I love how pet-friendly it is. There are so many small businesses here, there’s always something going on anywhere in Tampa Bay, really. It’s quite hard to choose. I’m not afraid of crossing the bridge and come over to St. Pete whenever something cool is going on, which is always. Take your pick, Seminole Heights in Tampa, Ybor, Dunedin. St. Pete has a special place in my heart just because of how unique it is. I love the art. There are so many creatives here and there are so many down to earth people that are making a difference in their little niche of the world, whatever that is.

What is one habit that you keep?

I like to do something for myself every morning. It makes me feel like the day is mine and not owned by work. Usually that’s reading. I’m working on the habit of maybe going for a run in the morning, I’m just not a morning person so it’s a lot easier to just cuddle up with Pina, a cup of coffee and a good book. Even if it’s just a 20-minute read, I like to do that. It makes me feel more in control of my day.

Who are some people that influence you?

I am obsessed with ultra runners. I ran a few marathons and I have done some adventure racing, but I’ve never ran an ultra and that’s kind of on my to-do list. I follow many of them, but two that I want to point out that encourage me are Sally McRae and Turia Pitt.

What is one piece of insight - a book, methodology, practice - that you would share with our readers?

I would highly recommend solo travel. That is such an important thing in my life. I went on my first solo trip out to Yellowstone and Jackson Hole in 2016 and I try to take a solo trip every year. You just look at things differently and find within yourself this sense of empowerment because you have to figure things out yourself. Whether that’s how to get around or mass transit, it’s just so neat and you see things in a different way and you get to interact with people in a different way.

What is one thing you wish you knew about your work 3 years ago?

That’s a hard thing to answer because what I’m doing now hasn’t really changed in the last few years, but one thing I would tell myself from three years ago is to slow down. I think everyone can take a moment to kind of repeat those words with me. You just have to slow down sometimes and reevaluate what you’re doing. Two years ago, I broke my ankle and that turned into blood clots in my leg. My CT scan revealed a bi-lateral pulmonary embolism. Weeks before, I had run a 17 mile race in Colorado and then I came back to Florida and broke my ankle and getting that diagnosis, that experience shook me and made me reevaluate what I do with my spare time and what organizations and people I give that time to.

What’s next?

Hopefully an ultra-marathon. I have my eyes on one in Florida in April. So hopefully by talking about it publicly, it’ll make me stick to it. There’s just something so awesome about that experience I really want to be a part of. I’m always open to opportunities, I think everyone should have an open heart to anything that comes their way.

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