Jessie Benson Knows the Key to Joy. (Spoiler Alert: So Do You.)

This month at Graymake, we’re attempting to bring joy to the world. Or, at least, to your world.

So when thinking of who we’d love to hear from this month, we thought of Jessie Benson right away.

Jessie is the founder and owner of B’More SUP and FloYo Fit,. She grew up on the water and, as a collegiate rower at Rollins, was able to combine her sports background with her love of water sports. A few years after leaving the rowing world, Jessie discovered stand up paddling and instantly fell in love.

Jessie has built a life for herself that is full of joy, mindfulness, empathy and just putting herself out there. We all could learn a lot from her.

Enjoy one of our favorite interviews to date!


Anne Hilb: Jessie, can you tell us about yourself and your work?

Jessie Benson: I am Jessie: a yogi, a world traveler, a fitness enthusiast, a teacher, a free spirit and a person who creates a life I love every single day.

I am the founder of FloYo Fit, a standup paddle board (SUP) brand that leads SUP fitness trainings, retreats and workshops around the globe. A large part of the FloYo brand is our FloYo Travels adventure retreats. I curate and lead 6-8 wellness retreats around the world each year.

In addition to running FloYo, I also own B’More SUP, a local standup paddleboard destination in Baltimore, MD.  At B’More SUP we lead SUP fitness classes, tours, lessons and corporate wellness on water events from May-October each year.

AH: How do you define joy?

JB: To me, joy is not just an emotion but also a state of mind, an attitude. We create joy by doing activities that excite us, by following our passions in life and sharing them with others. I believe if we do more of the things in life that excite us we will experience more joy in our lives.

To live joyously means living with the awareness that each day is the beginning of another new adventure. Each day is an opportunity to live life to its fullest. 

AH: What do you see as the difference between joy and happiness?

JB: I believe there is a profound difference between happiness and joy.

Joy is a choice. It is a choice that is available to us each and every day. Joy is not dependent on outward circumstances. Joy comes when you accept who you are, accept your life and start loving yourself and your life.

Happiness, on the other hand, tends to be externally triggered and is based on other people, things, thoughts, and events. 

AH: Do you think it is realistic that everyone can find joy in their work?

JB: Absolutely! I think people get joy and happiness confused and think they have to be happy all the time to experience joy. That is simply not the case. We are not going to find happiness in every single task we have to do at work.

For me, I have created two businesses based around my passions of stand up paddleboarding and traveling. Yet there are still daily tasks that I don’t love. I have to do my billing, update my website, manage my booking systems, and more. However, when I make a conscious decision to embrace these “boring” tasks and smile through the tough days, that is choosing joy. 

AH: What stands in the way of joy for people in workplaces?

JB: Many people have lost touch with what joy feels like. We have learned to constantly link our happiness with material things, with external circumstances, and we forget the feelings that come with choosing joy.

In the workplace, where we may be surrounded by negativity and a mindset of constant comparison, it is extremely difficult to shift into a mindset of positivity, gratitude and joy. Social media also plays a huge role, influencing what we think we should have, do, buy, like.

The truth is that you have everything you need and everything you are searching for within you. Cultivating joy will help you discover this concept of “enoughness.”

Our constant on-the-go lifestyles and multi-tasking also stand in the way of discovering joy. Many workplaces encourage and reward this constant notion of needing to do more, be more, achieve more. This prohibits joy.

We need to slow down and quiet our minds. When we get quiet in our mind—meditation, working out and breathwork can help with this— we can create space to listen to what brings us joy. And when we cultivate joy, we become more productive.

AH: Your work is highly seasonal. How do you do the work that brings you joy in the off-season?

JB: Although I cannot be on the water leading SUP classes in the cold winter months, I still make a commitment to do other activities that bring me joy. From teaching yoga and spin classes to traveling to warm destinations, my off-season is filled with just as much joy as the sunny summer months.

I believe that life is too short to put off experiencing joy. We need to cultivate joy today, and every day. We do so by focusing on self-compassion, being of service to others, expressing gratitude and surrounding ourselves with people who inspire us. These can be done every single day—no matter the season or where in the world I may be!

Building strong teams and a JOYFUL workforce isn’t black and white… 

We help companies thrive in the gray. To set up a 30-minute phone chat with a member of our team, sign up here or email

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