Anything BUT a Permanent Vacation…

The following may sound ungrateful. Harsh, even. But what I am about to describe is an island reality, a prevailing attitude among many in the hospitality industry. Namely, that working in tourism on a tropical island is far from a permanent vacation. At times, it’s downright draining.

Somewhere between six months to a year of working with the tourist public, you’ve become so weary of telling your island story that you must exert not a small bit of effort to keep from sighing and rolling your eyes when asked for the 378th time,

“So, how did you end up here?”

Or the keen, “You’re not from around here.”

Or the stupefying, “Do you live here?”

During my honeymoon period, I was thrilled to share. Starry-eyed and naive, I gladly recounted my tale of “getting bit by the tropical crazy bug” to anyone who’d listen. This lasted maybe six months – interspersed, I might add, with periods of despair and regret. Certainly, 10 months into my VI residency, after a series of Murphy’s Law life events occurred in rapid succession, I silently groaned every time a well-meaning tourist asked, “How did you get so lucky to live here?”

Some people start to invent backgrounds. I get why they do it. After being asked all day every day the where’s and why’s of your life, you get so tired of repeating your story that rewriting is necessary simply to preserve sanity. Otherwise, it’s akin to spending your days with a dementia patient – you just keep having the same mundane conversation over and over again. Not to mention, we’re often really busy concentrating on our jobs  during this impromptu interview. Plus, it’s really nobody’s business. My story includes info that needn’t be shared with every curious visitor. While I don’t make things up, the version I share depends on my time and mood, and their personality.

bar for Ashley's post_WWLOR

I’ve watched the honeymoon phase peter out in others too, sometimes with a bit of schadenfreude on my part. I am reminded of a young woman who briefly worked at a bar I frequent. Upon arrival, she was full of pep and sparkle and light. A fresh-faced, all-American girl on a post-collegiate adventure. Smartly dressed, hair swept into a perky pony, she exuded enthusiasm for her new life. On a weekday afternoon not long after she landed, I was venting to another local about some island inconvenience when she piped in,

“But look, honey, you have this to enjoy every day, ” while doing a Vanna White toward the (admittedly) gorgeous turquoise water and white sand mere paces away.

Since I hadn’t been to the beach in several weeks and had spent my recent vacation plugged into work correspondence, I couldn’t help but feel slightly annoyed with this Pollyanna business.

Fast forward a few months. I see the same girl at a neighboring bar, smoking cigarettes, sipping lunch wine from a plastic cup, baseball cap pulled down over her eyes, and well, not looking quite so sparkly.

Hmm. What can I say? Island life catches up with the best of us.

When I’m especially depleted from a lack of true free time in several days, weeks, months, even years, depending on your perspective, I can be downright indignant. But, I do my best to keep a lid on any resentment at work. And at home too, since, ya know…I live at my job. It may not surprise you that I don’t always succeed at this particular endeavor.

Not long ago, a guest offered what he surely felt was a compliment.

“You have my dream retirement job, you know,” he told me, a friendly smile on his broad white face.

“Well, you better expect to work really hard in retirement, then.” I did my best to match his smile.

Fortunately, my mom was visiting so I could bitch immediately to a sympathetic ear about his well-meaning but rather offensive comment. I hear a version of this all the time. That my reaction is so inwardly vitriolic, which I try to outwardly disguise, makes me feel even worse.

Because in reality, I do have a beautiful life. I live on an acre of lush tropical gardens with daily views that astound. I have no commute. Unless, that is, you count the 15 paces from cottage to office during which I watch hummingbirds and butterflies suck nectar from colorful flowers. I understand why my situation appears romantic. In some ways, it is. And in many more ways than I’ll burden you with, it’s not.

Speaking of romance, I’ll give you just one example. I’ve given up all attempts at discretion regarding what little dating life I enjoy. Every guest or owner on-site bears witness to all who leave and enter my cottage. You needn’t even look; footsteps are easily heard on the gravel pathways. Believe me, I know. Part of my job is to be intimate with the property’s noises. I can’t even have a private conversation unless I close the windows and turn on the A/C. So, as you might imagine, this ritual is essential if I’m lucky enough to get laid and want to ensure that my guests won’t hear me. And by my guests, I mean my customers.

Would I trade it for a 9-5 with a 30 minute commute in the city? No.

Would I trade it for a bartending gig on the beach? No.

But do I have a dream job living the easy life? Hell fucking no!

The reality is that those who are not independently wealthy and want to do more than just survive in the VI have to work their asses off. Especially if they have designs on raising a family and providing their children with a quality education. Living in the Virgin Islands is anything BUT a permanent vacation.

road for Ashleys post_WWLOR

The annoying part isn’t so much that island life doesn’t equal a perma-vacay. What irritates is the constant perception that it does. When well-intentioned tourists constantly inquire as to your personal story and insist that you’re “living the dream” (WTF does that mean anyway?!) when you’re actually working harder than ever before, and for less money, and you can’t even recall your last beach day, sometimes it’s hard not to tell them to go fuck themselves. This is especially true if you were under the same impression as them before your big move. Then you want to tell yourself to fuck off too.

When people are unsatisfied and bored with their own lives, they idealize what they see on the outside lives of others. It’s obvious in the way we worship celebrities, even though their lives are just as difficult as ours often seem. But people are so hungry for something more. Something different. Something other than icy commutes, mundane routines, mortgage payments, and asshole bosses…that they’re quick to place more value on the daily experience of others than their own.

It’s just as easy for me to idealize the lives of my married friends back in the states. They’re all so clearly in love with the babies they’re making. Facebook photos show cozy, family-filled scenes. Children filling lives with joy. Had I not moved to an island, this would be me. The solitary posts I offer of tropical vistas and my dog can feel rather lonely in comparison. But I’m not seeing photos of marital strife and honeymoon stitches, intrusive in-laws, and kid puke in the bed.

Celeb mags are photoshopped to the hilt. Reality TV is rife with scripting and manipulative edits.

And paradise does not exist.

Or, perhaps more accurately, paradise is what you make it. Because when you finally bring your fantasy into reality, the inevitable cosmic dog shit of real life will make its way there too.

Where you live matters. What you do matters. But what matters more is the lens through which you view your circumstances.

A lesson it would clearly behoove me to take from myself.

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34 thoughts on “Anything BUT a Permanent Vacation…

  1. After living on an island for two years and now in Miami for 15 years,I can absolutely relate with everything you said. Although my life on the island taught me many things,it is definitely not something I would try again (unless I could find a safer island and had a lot of money). And here in Miami I work 10-hour days and have not had a vacation in over two years,yet me family seems to think that because people come here to vacation, then my life must be a permanent vacation too.I also appreciate the beauty that surrounded me on the island and here too,but a “dream job”? yeah…notsomuch!

    • Palm trees and beach does not a permanent vacation make. Thanks for reading and commenting- I hope you get some sort of a vacation very soon!

  2. island life is a double edged sword.
    And the economy of the Caribbean has for hundreds of years been corrupt, and pulled and pushed around by thievery, piracy, and contraband. Its also beautiful, and the people are friendly, and often trustworthy….but for an American. even if youre not at the end of your line….it will never be a life of leisure….its always just a bit more inconvenient than you bargained for.

    • Yes- I have moments, often within the same 48 hour period of time- where I think, “How could I ever live anywhere else?” and also, “Am I freaking crazy for living here? What’s wrong with me? Why can’t I be satisfied with the suburbs?”

  3. After reading this twice and I finally stopped laughing. I’m gonna guess you had a really bad day or month or two.

  4. I appreciate this post as I am one of the visitors who always asks, “how did you get here?”. I often ask because for 18 years now, since the first time I stepped foot on St John, I’ve dreamed of living in the VI. It makes complete sense that it can be annoying to someone who may have been asked a 100 times already that day. I can relate to similiar annoying comments as I worked in retail for 15 years and when something wouldn’t scan or “ring up”, I’d always hear from the customer “I guess that means it’s free”. Uh, no. Not free, you dummy. Anyway, my husband and I have been seriously talking about taking the plunge, leaving our Colorado home and “living the dream” for a year or so. We know we’ll work real hard and fortunately that doesn’t scare either of us. We will be there in July and will be mindful of the dreaded question, “how did you get here?”. Thanks~

    • Hi Jen! Hey, if it wasn’t worth it, I wouldn’t still be here almost 5 years later. It’s great if you and your hubby know what you’re getting into, and it sounds like you do. You know- most of us don’t mind talking about how we got here, or giving you some version of our island tale….it’s just hard when we’re really busy doing our jobs to stop and tell starry-eyed tourists how we got here. It’s better if you ask someone who has time to converse and isn’t on the clock. Or just find the right person who loves to talk about themselves!

  5. I found this blog yesterday and love it! I am also from Minnesota and have been researching a move to USVI when my lease is up in October. I don’t plan on it being a permanent vacation at all; I’ve always had to work hard for what I want and I don’t see that changing anytime soon! I know you hate questions, but I’m hoping you still have that ‘Minnesota nice’ attitude and don’t mind 😉 — I’m just wondering if you have any pointers on what neighborhoods to look for or any apartment ideas for St Thomas? I don’t plan on bringing a car or buying one; I’m thinking it will be more of a seasonal move, 6-7 months. Was it easy for you to get your first job? I’m in the bar industry in Minneapolis right now… How reasonable is it to think I can bring my cat? Anything would be helpful! But I also understand if you don’t reply! haha…

    Thank you!

    • Hi Andrea,

      Glad you found and are enjoying the site! I’m going to reply for now, as Miss Ashley is a busy bee at the moment. Though I am sure she would reply to you, as she IS nice like that (out of Minnesota-y-ness or out of her inherent Ashley-ness, one can’t be sure). As for moving to St Thomas (I lived there for 3 years before moving to the BVI), I would caution you against not having a car. It’s a big island and spread out and not being able to get around it can cause a lot of unhappiness and public transportation leaves a lot to be desired (it’s practically non-existent). If you are dead set on the no car thing, then I’d probably suggest trying to find both a job and an apartment in either Red Hook or town (Charlotte Amalie). Bartending jobs are often available, but competition can be tough and don’t be surprised if people won’t hire you until you’re already down here (most are contacted by dreamers daily and want people to prove that they’re here for a bit before going through the efforts to hire them). As for the cat, I brought mine on a carrier on the plane – since it’s US to US, you just need a health certificate stamped within 10 days of travel for the airlines.

      Hope that helps, best to you!


      • Thank you for the quick reply! I’ve been looing mostly at the Red Hook / Sapphire Bay area. If you don’t suggest being car-less, do you suppose it would be easy then to just purchase a cheap/beater car and then sell it again before I depart? I just can’t justify shipping over my [foreign made] car for only 6-7 months after reading about all of the fees and extra expenses.. Thanks again, any advice I can get is greatly appreciated!

        • Yup, it is a common saying on STT that there are more cars than people – no need to bring anymore down. I actually purchased a beater Suzuki (the car of the islands), had it for 3 years, and sold it for MORE than I bought it for when I left, if you can believe that! Just bring down an extra few thousand dollars so you can get yourself some form of transportation – if a cheap beater is what you want, there are usually plenty for sale in that $2500-5000 range.

  6. Having owned two bars for the last 10 years of our lives, with kids on this island (Cozumel), we’ve developed an entire thesaurus of responses concerning the “man, you’re living my dream” people. Mostly, they are well intentioned vacationers trying to give a self-depricating compliment. I appreciate the sentiment when genuine, however the best I can muster nowadays is not what it used to be. Usually, at this point I’ll look them straight in the eyes and very ‘matter of factish’ slowly state to them that “the majority of dreams are better enjoyed while sleeping.” This then elevates their view of me from mere cool guy that has it all role model to that of a timeless sage. Sometimes I might add “you have to be careful with this business of accomplishing your dreams.” “why” they say.
    “because if you catch all your dreams, you’ll have nothing to look forward to would you?”….
    Conversation over.
    Nice post, thanks!

  7. Interesting post, I guess I’d never thought to move to the islands until I was financially independent because it seems like it would be hard to find good jobs that weren’t pre-selected for a “belonger”, especially when the COL is so expensive there. That would eliminate a lot of the cool factor for sure.

    The upside is experiencing the paradise when you are young enough to enjoy it I guess. But I guess I’d rather grind it out here and show up there when it would truly be a permanent vacation.

    Guilty of asking “how did you end up here” Didn’t even think that question would be so annoying you’d have to make up a response.

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