It’s quite simple, really. Come here with a large one.

A cynical joke, to be sure. But accurate. And I’m glad I heard it from one who knew soon after I was bit with what I call, “The Tropical Crazy Bug.” Like the no see’um, this bug is impossible to detect visually, but the reaction from those susceptible to its venom is unmistakable. Victims present a sudden, unshakable infatuation with the notion to leave their lives as they know them and move to the tropical island that stole their hearts (and brains) upon infection.

I harbored several unrealistic fantasies about island life before moving to my rock. Otherwise I surely wouldn’t have made the wholly illogical leap. But these dreamy desires were tempered by warnings about the high risk of failure and despair from my already-on-island kin, for whom the fantasy of living in paradise had long worn off.

At the time, I certainly respected their dour sentiments, but now I actually understand them too. To be clear, I love my islands. If not, I wouldn’t make the effort to stay in such an expensive, inconvenient locale. But I have grown quite familiar with the realities of running an island business. And so, I must suppress the urge to turn total killjoy whenever I hear someone who has only ever vacationed in the islands wistfully romanticize about moving to paradise and opening a small business. I’ve heard several varieties, none of them particularly surprising: coffee shop, taqueria, beach bar, B n’ B. Honestly, the last thing I ever want to do is belittle a person’s dreams, but in these situations it takes every bit of restraint I have not to piss out their sparkle before they can finish their sentence.

I know all too well how easy it is to fantasize about a different kind of existence when your daily routine has becoming utterly boring or loathsome. It’s even worse when you don’t particularly care for your job, your partner, your climate, or any other aspect of life that’s damn near impossible to avoid and would take more than a little courage and effort to transform.

Still. I cannot stress enough that island life is anything but a permanent vacation.

I’ve witnessed multiple mini-breakdowns / burnouts (including my own) among otherwise highly-functioning managers and owners. I’ve seen many new businesses come and go, including several that seem to have changed hands more times in five years than I’ve traded in my old Reefs for new ones. I’ve watched as enthusiastic, extremely competent people buy a business, all straight-shouldered and optimistic. And six months later, I spot them dragging ass to happy hour, looking exhausted, if not utterly defeated.

Easily the biggest impediment to business success in the tropics is the outrageous utility bills. In the VI, we pay roughly 300% over the stateside average for service that fails regularly, and even when operating, manages to surge high enough to fry electronic equipment. Does the utility company offer any assistance replacing your dead freezer or computer after one of their destructive power spikes? That would be a resounding no. This is the main reason everything is so expensive here. It’s a foundational problem that affects EVERYTHING.

So start with the shoddy yet luxuriously-priced electrical grid and add the more obvious reason for the high cost of island goods and services, namely, that everything must be shipped across the ocean to get here. If you’re on a secondary rock (like I am on St. John), add more expense. This also impacts the consistency and rapidity with which products are available for shipment. Not to mention condition upon arrival.

Then pile on the Caribbean culture of low urgency, and you’ve got yourself a pretty massive hurdle to success before you even focus on anything strategic or complicated. All of this means that even the most basic of business transactions – things that should be simple and seamless – can turn into anything from a major pain in the ass to a full on nightmare.

Take, for example, the following exchange I witnessed at the bank last year:

Business Customer: “Good Day. I need $500 in change – mostly small bills, please.”

Bank Teller: “No ones.”

Customer: “…You don’t have any singles?”

Teller: “Not as yet.”

Customer: *pause* “Oh. Well…isn’t that sort of like, uh, basic?”

Teller: *Stony-faced silence*

Customer: “Will you be getting any in today?”

Teller: “Yes.”

Customer: “Do you know around what time so I know when to come back?”

Teller: “I don’t want to tell you a time because if the boat don’t come by the time you come back, then you’ll have made a trip for nothing…”

Customer: *Sigh* “Okay, give me what you can without ones, and I’ll just have to come back later if I find time.”

Might I add that this branch’s convenient banking hours are weekdays 8:30am – 3pm.

One suggestion I have for anyone trying to run a successful business (or life, for that matter) in the islands is not to wait until the last minute for anything. I have yet to employ this adult habit myself, which has not been to my benefit. Offices frequently close early or you discover that additional items of identification are required or some other such surprise, so if you don’t start the process way before you think necessary, you’re apt to miss the deadline altogether.

Such was my fate last year on the corporate tax due date. Back then, I had more on my daily docket than even the most productive person could accomplish, and so it was past three when I drove down the hill to drop the returns at the tax office.

For the past two years, I’d been to the IRB monthly to pay hotel tax. I knew they stayed open until the late bureaucratic hour of 4:30pm. I arrived at 3:55 to find the door locked. Curious. I went round to the other side of the building where the Department of Motor Vehicles operates and tried to open that door. I had barely turned the knob when the door flung open, almost hitting me in the face, and I was met with the angry countenance of a woman who asked, accusingly, “What are you doing here?”

I jumped, startled. Was this private property? Was I trespassing? No… this was, indeed, the same government office I’d entered dozens of times over the past two years.

“I…uh…I’m just trying to drop off my corporate taxes. The other door is locked.”

“He gone for the day.”

“Gone? I, uh, I thought they didn’t close ’til 4:30.”

“Well, I can’t speak for that office, I don’t work for them. But he gone.”

“Okay…are you closed too? I’ve never been here when the door was locked before. It’s still early.”

“We lock the door after a certain time to keep the women working in here safe.”

More like so they don’t have to deal with customers on a Friday afternoon. Even the ones who want to give the bankrupt territory some money.

Despite the significant challenges, success is possible. In addition to structuring one’s schedule to operate far ahead of deadlines, I’ve observed the following (most are oddly paradoxical) qualities among island business owners who’ve had success:

hard-working yet laid-back,
persistent yet yielding,
determined yet flexible,
good-humored, appreciates the absurd,
confident yet humble,
authoritative yet respectful,
patient yet proactive,
a non-destructive relationship with drugs and alcohol.

Businesses with the most staying power have owners and managers who live on the island, are engaged in the community, treat their staff like family, and maintain a consistent level of quality. Not easy. But possible.

The best piece of advice I have for the dreamers – those victims of the tropical crazy bug who fantasize about starting a little business on an island and whiling their lives away in peace – is to do a little trial run. Spend at least 6 non-committed months on your island of choice working for someone else first.

Unless, that is, you really do have a large fortune you’re looking to shrink. In that case, by all means, hop on down and give it a try. You’ll find several small businesses for sale in the local real estate guides. Take your pick!

Written By:

Current Rock of Residence:

St. John, USVI

Island Girl Since:


Originally Hails From:


Ashley lives on St. John in the US Virgin Islands where she can be found drenched in sweat while communing with the hermit crabs who live in her yard. The irony of living in a shac-teau on the most remote part of a tiny secondary island in the Caribbean while spending the majority of her time with a creature named after people who prefer solitude is not lost on her.

Despite constant inquiry as to how long she’ll be on St. John, Ashley has learned in her three decades on this planet that setting one’s life plans in stone is the best way to ensure their futility. For now she remains enchanted with the beautiful absurdity on her rock of residence, which is colorful in far more ways than one.

You can hire her to write and design for you at Bad Ash Babe Creative.

Want to read more posts by this writer? Click here.

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