The expected life span of an activities director at a resort is roughly one year. To say it’s exhausting doesn’t do it justice. As the entertainment team supervisor, I came up with all the daily activities—a different one for every hour, from 8 a.m. to 5 p.m.—and developed the shows and contests we’d put on at night. I was constantly thinking up new ideas and testing them out. Plus, you’re always on call to make sure guests are having fun. Want to go to sleep? But there are some people down by the beach bar who look bored! Go do shots with them! I often didn’t get to bed until 3 a.m.
A big part of the job is mingling with guests and joining in on the resort’s games and group activities—which often involve alcohol. But you couldn’t actually be drunk on the job, or you’d get fired. Over time, the bartenders learned to recognize when we wanted (or needed) shots of apple juice instead of rum. Most of the time, I wasn’t doing those shots with the guests like they thought I was. I couldn’t have.
It sounds hokey, but what I liked most about the job was meeting new people every day from all over the world. We got a lot of repeat customers, and I still keep in touch with some of them 12 years later. Another upside of the job was living on the property: We each had our own rooms and private bathrooms in cottages with big living rooms and kitchens—not that we needed them, since we also ate for free at the resort. We were lucky: I’ve heard horror stories about the housing for staff at other places.
Many guests think the "no gratuities" rule is gospel—and it is, officially—but everyone gladly accepts tips, anyway. The pay isn’t that good, and at our resort management turned a blind eye as long as the guests were happy and you were being discreet. And yes, tipping well does get you special treatment. Here's what doesn’t: Leaving us your leftover rum or illegal substances as a farewell gift.
This job is all about customer service, and I always had to remind my staff that the guests don’t care if you’re having a bad day, you still have to slap on that smile. Some people can’t hack it—can’t separate their personal lives from work—so we had a high turnover rate. But people are paying thousands of dollars to be here, and they don’t want to be with a sourpuss.
That movie How Stella Got Her Groove Back changed life for all the male resort workers in Jamaica. Women started coming from all over the world to find their own personal Winston. They’d be alone or in packs, sitting at the bar and picking which resort workers to go after. I actually know men who ended up marrying their lovers or moving to the U.S. to be with their trysts. But it’s definitely a young man’s game. After 25, 26, most men quit the life.
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