KINGSTON, Jamaica — For Jamaican comedian and content creator Karlando “Bad Sekki” Bailey, his first trip to the United States will be about more than sightseeing and creating content. One of the moments he is most looking forward to is reuniting with a cousin he has not seen in years.

The entertainer, who is scheduled to depart Jamaica on Monday, November 16, shared his excitement during an exclusive interview with the Jamaica Observer, revealing that his cousin has been eagerly counting down the days until his arrival.

“She can’t wait. Every day she call me and say, ‘When again?’ because it’s been a long time since she has seen me,” he shared.

The reunion carries special significance for Bailey, as his cousin was also the only person he confided in about his US visa application process, making her an important part of a journey that has been years in the making.

“I feel good, I feel happy,” he said when asked about his upcoming trip.

Bailey secured his US visa in October after being denied on his previous attempt in March 2025. His departure will mark the beginning of a 17-day visit to four American cities under the Bad Sekki Goes to America project, which will see him reconnecting with family, exploring new surroundings and creating content for his growing audience.

While the family reunion is high on his list of priorities, the comedian is also eager to experience New York City, where he has already envisioned a special video.

“I want some sweet content. The one thing I want to do is visit New York and do a video singing ‘In New York’. It just look sweet and the place just pretty. A Half-Way Tree me normally affi do it,” he said, laughing.

The trip represents another milestone for Bailey, whose rise from working as a security guard to becoming one of Jamaica’s recognisable social media comedians has opened doors he once could only imagine.

Reflecting on his development as an entertainer, Bailey admitted that overcoming his naturally shy personality has been part of his growth.

“Mi work pon the likkle shyness,” he said with a laugh.

“But now it’s not so bad. After a while, when you start working in the space, you go get used to it.”

Known for his humorous and often unpredictable videos, Bailey said much of his creativity comes from allowing his mind to wander.

“My brain strays a lot. I would just be sitting here and just zone out and start thinking about random things,” he explained.

Despite his growing popularity, the entertainer admitted that he once questioned how long his success would last, a concern that continues to motivate him to experiment with new ideas and remain consistent.

“I thought I would have fallen off already. That’s why I’m always changing the game,” he said.

For Bailey, the determination to keep producing content is also rooted in his desire to avoid returning to the financial uncertainty he experienced before finding success online.

“Me nuh wah do back the security work enuh, so I make sure to do more content so I don’t go back,” he said.

As he prepares for his first international adventure, Bailey is looking forward to bringing his humour and creativity to new surroundings while making memories with loved ones.

READ: Bad Sekki jets to NY