There are many reasons that you might be interested in working while you are in the Caribbean. Semi-retirement is becoming much more common as people are finding that they need to supplement their savings in order to maintain a desired lifestyle. Staying busy through working is also desirable for many people who love their jobs. And, telecommuting or self-employment via the internet is particularly appealing if you can work from the Caribbean!
There are countless scenarios involving working in the Caribbean, but let’s take a quick look at a few possibilities and what they entail. Remember, regardless of where you work your home country may still require that you pay taxes there. Check with an expert.
Employment abroad
Being hired as an employee by a company in a Caribbean country is quite difficult. A work visa or permit must be obtained and many countries set a high standard for getting one. For example, it may be necessary for the employer to show that the position could not be filled by a resident of the country. There are also frequently quotas that require companies to hire a certain percentage of local residents.
Freelance work for a Caribbean company
Some Caribbean-based companies get around the foreign employment restrictions by hiring freelancers or sub-contractors rather than employees. While this may be a possibility, proceed with caution and remember that a work visa is still required. Also, this would be considered domestically earned income and may be taxable by the the host country (in addition to your home country tax requirements). Ask an expert for clarification.
Telecommuting from a Caribbean country
There are two possible telecommuting scenarios. In the first, you would be working as an employee for a company in your home country and in the second as a freelancer or consultant for a foreign or home-based company. While these situations still may still entail “working” in the Caribbean country of your choice, the fact that you are employed in or have clients in another country, are paid in another country and do not transact any business in your host country may keep you under the threshold of doing business. Check with an expert!
Self-employed on the internet
Similar to the above situation is running your own internet-based business from your computer, assuming that your business is registered in your home country, or at least outside of your Caribbean host country and that you are paying taxes there as well. Again, it is best to check with an expert.
Buying or starting a business abroad
Unlike many of the above scenarios, Caribbean countries in general encourage foreign investment and sometimes reward investments through relaxed residency and citizenship requirements. Investments often take the form of purchasing real estate but can also include purchasing or investing in an existing business or starting a new one.
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