For the Freedom File, I was thrilled to interview the most free person I know. She is free-spirited, free-thinking and free-living. She does her own thing and she doesn’t give a flying f*%k what you think about it. She doesn’t follow any trends (accept maybe wearing her fave, LuLuLemon). But even where LuLuLemon is concerned, she is not wearing it because it’s popular or trendy. She doesn’t care about what all the cool kids are doing (because let’s be real, she is the cool kid). She cares about the right things. Like her soul, her purpose, her impact and her connections.

Jessie Benson is the owner of FloYo, a full-body workout performed on a standup paddleboard combining yoga sequences and interval training methods. On water. Yes: floating yoga. Yoga-pilates fusion on a paddleboard. You try executing a Downward Dog atop a paddleboard in the middle of the ocean. Talk about commanding balance. It forces your mind to think of nothing else.

But what if you fall in?” Jessie hears it every day, but she’s also living proof that you can nail some of the most challenging, balance-demanding yoga poses (like freaking head-stands, okay.), and float back to base dry.

Jessie was the first person who showed me you could work because you like what you do, not because you need a paycheck. She jets from place to place for the opportunity and potential of each journey and destination – for the ultimate freedom of flexibility, space and time.

Jessie is so committed to her mind and body wellness, she wouldn’t even meet me for happy hour for this interview. We met at a local cafe instead and got right down to business, sans wine…


BFD: Some entrepreneurs can be doing work they love, but feel trapped by the very empire they’ve built. Even with everything you have to do for your business, taking care of your business and promoting it, managing it, it still makes you feel free?

JB: Definitely. There are times when I feel like my to-do list is so long and I have so many things to do, but ultimately it’s up to me if I do them and I do them because it makes me happy to grow my business, not because I’m under the pressure of someone looking over my shoulder telling me I have to.

In order to feel free,  sometimes you have to do something that’s scary. You have to drop your fears. It was scary taking that step, leaving the corporate world and starting FloYo. It was scary leaving Baltimore and starting FloYo in Nicaragua. But sometimes you have to do that – take that leap of faith in order to feel happy and free.

BFD: Did it make you feel free right away? What was the moment you realized how free you were and what did that feel like?

JB: I don’t know if one moment stands out. In Nicaragua – it wasn’t until I actually got there and had a whole day with nothing to do. I could do anything I wanted. It was pretty awesome. No kids. No mom. No one I had to report to. No one even knew me or knew who I was.

BFD: What was it like having no one know who you are?

JB: It was lonely at times. But it also took me out of my comfort zone. I couldn’t afford to be anti-social and I haven’t had to extend myself like that for a really long time. In Baltimore, Ive always had a network of people at the gym and dog park that I always knew, so I never had to make an active effort to meet new people.

BFD: What is your go-to conversation starter when you meet a stranger?

JB: In Nicaragua, it was always about paddle boarding. It’s usually fitness related. I’m great at self-promotion. I can talk about FloYo all day.

BFD: Does coming back to Baltimore make you feel less free?

JB: I feel like when I’m here, I need to be more busy. I feel like I have these commitments that I’m tied to. I have people that want to see me, a full schedule of events I could attend. In a way, that’s less free.

When I came back from Nicaragua, I stayed home an entire week and didn’t see anyone (despite all of the requests). I felt in my mind when I left, I was leaving. It was indefinite. When I came back to Baltimore, I wondered, “Am I failure in some way for coming back?”

I wasn’t really prepared to answer questions about why I was back and facing the people that I left made me feel a lot of pressure to address that decision. And I think that was sort of why I didn’t want to see people. I thought people would ask, “Oh you’re back? Why are you back here? I thought you were moving to Nicaragua for good?” And though that was never my intention, I didn’t know what was going to happen when I got there or how I would feel about living there and how long I would want to stay. I didn’t know if I would want to be there for a month or a year.

I think that was part of the reason I wanted to be a “hermit” at first. But I think life is so busy here…In Nicaragua, there is nothing to do. You’re in the middle of nowhere. To get to the nearest town is an hour bus ride on a dirt road. But when I’m here and there is so much to do, and I’m getting Facebook invites and – yesterday there were five things I could have gone to. – In Nicaragua I wasn’t on social media much and I didn’t care, but for some reason, when I’m here, I need to see what everyone is doing all the time, and for some reason it delivers pressure to be busy or as busy as everyone else! It’s weird! But, it happens whenever I’m here.

BFD: Why do you feel so much peer pressure to keep up with everyone else?

JB: Part of it, is when I’m not busy and being social, taking classes and going to happy hours, I get lonely here. In Nicaragua, I used to get lonely, but it was only because I didn’t have anyone I felt really close to that I could talk to, but here I immediately feel lonely if I have an hour I’m alone by myself. Even though I had eight hours alone by myself every day in Nicaragua. That’s something I always struggle with is making sure I don’t have enough free time to start feeling lonely.

BFD: In terms of being free, you move to Nicaragua, you have an incredibly free lifestyle, yet you’re so limited by things that you don ‘t have readily available, like groceries. How did that limit your freedom?

JB: Yeah that’s true! We were isolated. Two and a half hours from Minagua. I didn’t have a car. You would take a local chicken bus, an old school bus, for an hour to Rivas, the closest town. Sometimes you would be sitting next to a pig or a chicken. I went to the grocery store twice in the whole three months of time I lived there. There were only two restaurants or bars you could go to. Everyone went to bed when the sun went down and woke up with the sun the next day.

But at the same time, that’s why I liked it so much. You really slowed down. My mom goes to the grocery store every day and I tell her how crazy that is when you could be spending more of that time with family. You look at the kids and they could entertain themselves on a small dirt porch with one truck – they have one truck – that they’re playing with for days and weeks! And you look at kids here, and kids get bored after five minutes with one toy and so houses are filled with toys in excess. I think it’s just different. That’s the way life was and I adjusted to it. I didn’t feel a loss of freedom from not having a car. That was the way life was and I chose to be there and I appreciated it for what it was.

BFD: So what does your family think about your free lifestyle?

JB: I think my dad really respects what I’m doing and he thinks it’s great. I mean this is the life that I wanted. I wanted to be able to travel and do what I love which is teaching yoga and FloYo. I think he’s really proud of me for doing that. My mom doesn’t get it. She doesn’t understand why I want to do it. She’s really content doing the same thing every day and doesn’t give much thought to where she’ll be in five years or ten years. She doesn’t plan. Not that I’m a planner necessarily, but I know this is the life I want to live and I’m going to keep chasing after that.

I think people think I’m a little bit crazy. But I think that they’re crazy for just wanting to stay here and live a boring life, in my mind. Even when I have kids, I don’t want to just be here, I want to go everywhere.

BFD: What do you think your nieces think about your lifestyle? How do you explain it to them?

JB: They knew I was in Nicaragua. I don’t think they know where that was – they’re five and three. I think they think it’s cool. Camden wants me to show her yoga poses all the time. I think they think it’s cool Aunt Jessie is in all these different places, but they’re really happy when I’m with them, too.

BFD: What do you want to teach them about being free and living a free lifestyle? What do you hope they pick up on?

JB: I hope they know they can do anything they put their minds to. I still don’t know what I want to do forever, but I’m very confident that I can do anything I put my mind to. And I want them to feel like that and they don’t have anything tying them down or holding them down. They don’t have to live the way their parents do. Never settling for the life their mom or dad tells them they’re going to have. Dreaming big and chasing after that.

BFD: Are there any yoga poses that sort of really embrace the idea of freedom that you can think of?

JB: I was in yoga today doing a Chair Pose. And Chair Twist. You can stay in Chair Twist, or you can open up and do a bind. You can come up into “Bird of Paradise.” And Bird of Paradise is one of those things…you pick up your leg and that’s scary! I don’t want to pick up my leg because I might fall over. And then you kick your leg straight out after lifting it up. So, for the longest time, I would just stay right here in Chair Twist. I didn’t trust the right leg that I could come up and straighten it. I was doing the pose in class today and I wasn’t sure if I had the strength to come up. And once I came up, I felt so free – I did it! If I can do that, I can do anything! So I think that’s a great example. You can stay where it’s comfortable, I could stay there all day. Or you can take that risk, lift that leg, and go for it! And that’s what I’ve been doing with my career. With my life. I don’t really know what I ‘m going to do when I get up there. Some days, I might be able to straighten my leg. Some days I might not be able to, but I’m going to try. I’m going to go after it. And that’s free.

BFD: How has this free lifestyle changed your perception of relationships with men, friends, and how has it changed the way you think about having a boyfriend or having a friend?

JB: I want to be in a relationship, but the way my life is and living the life I’ve chosen, makes it a lot harder to meet someone that I might want to settle down with. I don’t think there are as many men who live the life I do. Most men I meet live in Baltimore and have a job and a house and they don’t have this same ambition or drive I have.

Being at the festival in Costa Rica made me realize there are other people like me! Other people who are really passionate about what they’re doing and genuinely want to learn about other people and other cultures. I connected really quickly with other people there because we were so similar and it made me realize I don’t connect with men here a lot because we don’t share that sense of exploration and freedom. They don’t have the desire to go out. People who are like me are more open and more open-minded and accepting. They accept people for who they are and what they’re passionate about.

BFD: You found your tribe. Your freedom tribe.
(she glowed a little when I said that.)

BFD: How do you think people in Baltimore can live more freely?

JB: I think they need to get out of Baltimore. They need to break out of this perpetually busy, materialistic life. Get out and explore.

If you want to find true happiness, you need to find out how to be free.