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For Tanner, island life offers a particular set of challenges. Power goes out sometimes, though usually with no loss of cell phone coverage, she says. If it happens, she takes her laptop to a beach bar.
“Anguilla has free Wi-Fi all over,” she says. “And if I'm in the mood, I'll call my teammates on a video call and rub it in.”
And there's the weather. “We're first in line for the hurricanes,” Tanner admits. But they usually haven't reached their full growth yet when they hit Anguilla. Over the past eight years, there were only two major storms, which knocked out power for a week, she says. And tropical islands aren't unique in having adverse weather events.
“Everybody deals with natural disasters in some way or another,” she says. “I just happen to be dealing with hurricanes. Right now [early June], my colleagues in Austria are dealing with horrible floods.”
Other downsides include the lack of chain stores, car dealerships, supermarkets – if it's not for sale at one of the small island grocery stores, it has to be shipped in, which takes a lot of time, and money. As a result, Tanner buys multiples of everything she really needs.
Foreign countries – and this includes most of the islands in the Caribbean – love getting tourists and retirees, who just come to spend money. But they are more hesitant to accept working-age adults as permanent residents, since they might compete with the locals for jobs. It is usually easier for a telecommuter to create a brand new company that they own, and get a self-employment visa, than to get a work visa.
This is what Tanner did so she could work in Anguilla. “There's legal paperwork that has to be done, and has to get renewed every year,” she says. “But it is doable.”
The process varies by country, and can become time consuming – and expensive. Eventually, countries will probably figure out that telecommuters aren't competing for local jobs, but are instead bringing in spending money, networking opportunities, and high-tech skills to the places where they settle. Instead of making it difficult to relocate, they should be actively trying to attract telecommuters, they way they now market to vacationers and retirees.
Until then, however, if your Caribbean destination is a U.S. territory – like Puerto Rico, or the U.S. Virgin Islands – then you can avoid all the paperwork.
“It's part of the United States, so you don't even need a passport to go there – you just need a driver's license,” says Matt Bauer, co-founder and director of St. Croix-based ConnectSpace.vi and president of BetterWorld Telecom in Reston, Va. “It's like moving to another state.”
Bauer, who splits his time between the island of St. Croix and California, says the cost of living on the island is a bit higher than, say, in a rural town in the midwest. But there are supermarkets, K-Mart, Office Depot, even an accredited university – the University of the Virgin Islands.
Best of all, St. Croix is one of the 10 most concentrated places for Internet traffic in the world, since two major Internet pipelines meet here. Local authorities are currently putting in about $300 million worth of new infrastructure to expand local connectivity to these pipelines, paid for with U.S. stimulus grants and private business investment.