Under Yuh Skin

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An American who calls Kingston home

“New York was never the dream,” says Benjamin Bailey, an ad-land Creative Director who spent nearly double decades in Gotham building a golden portfolio of work for the world’s biggest brands. It’s simply where this mild-mannered, Mississippi-bred, major talent had to go to make it happen. “I fell into the New York cycle of competition, where everything was dialed up to 11, but my whole background was coming from a place that was placid—I learned to run the race, but it simply wasn’t my character,” he explained.

It was 2003 when Benjamin found himself working on a project for Island Records legend Chris Blackwell, and each visit to the Rock brought a deeper meaning. It’s the thing that happens for some people in Jamaica: the mystique unleashes. He felt the steady reggae pulse, deep rebel soul and ceaseless warmth. Kindness abounded. Creativity astounded. With his signature soft-spoken sincerity he says, “I went because one of Jamaica’s best visionaries said ‘come and help me.’ I owe Chris a lot of gratitude. I can’t think of a better way to enter the fold.” Benjamin began to imagine a life he couldn’t yet define. He just thought to himself, soon come. And soon, it did.

“My resolution to move was atypical. I didn’t overthink—I just decided to do it. I sold my apartments and gave away my stuff,” Benjamin recalls with a smile, still a little unbelieving. Nearly 9 years on the Rock seems to have done this unlikely expat endless good. When he tells people he’s very nearly 50-years old, they are, without exception, astonished. “Kingston feels like dialing back time. I like that stores are closed on Sundays and you do business on a handshake,” Benjamin says, “I’d finally come to realize, is that it felt like home.”

Benjamin didn’t fully intend to start a business, and it was anything but easy, but the potential to work with bright young minds became apparent: “In the first two months so many people knocked on my door, and the network of talent became undeniable,” he says. There was a lanky programmer with locks to his waist working at the newspaper. There was an illustrator, a writer and a cache of young designers. “There are three ways to do something,” Benjamin explains, “You can do it yourself, you can dictate to someone ‘make this blue’—or you can teach what’s in your head. It’s much harder, but I very much enjoy taking the time to train and guide.” In a subconscious nod to this genial philosophy, Benjamin would call his company Generousitas.

Some of the initial employees never left, and since the boutique creative agency opened doors they’ve accomplished a lot. Everything from building a beer brand from scratch—to quietly advising, writing and designing key parts of the campaign for the People’s National Party, which enjoyed a landslide victory just a handful of months ago. In addition to local projects, Benjamin continually leverages his never-waning NYC connections to bring US and global work to his able Jamaican team. To name a few, behemoths like American Express, Verizon, Bacardi, Coca-Cola and even Baskin-Robbins China have seen stellar work from this Kingston shop. And it makes complete sense when Benjamin asks, “Why wouldn’t you want to hire creative talent in one of the most prodigious places on the planet?”

An island lifestyle is an enviable thing, and when asked to describe his own, Benjamin leans back and warmly recalls, “When I first got to Jamaica someone said to me, ‘every chance you get, take your shoes off and walk around barefoot. Take your shoes off and touch the ground.’ That’s the best way to describe my lifestyle—my feet are planted.”

Check out generousitas.com to see more.

Digging Jamaica? Visit the 100m Shop and get your jerk-reggae-patois-sunshine fix. (Sunscreen recommended.)