Freelance Writers: How to Live/Work Full-Time from the Caribbean (Yes, It’s Possible!)

If you’re a regular reader, you know that I’m American, but have been living and working full-time from the Caribbean (Jamaica) since 2014. I can’t tell you how many hours I spend in bars or on the beach explaining to people who are on vacation how and why I did it.

It just fascinates them and they wonder, “Is this something I can do? I’d love to be able to be here all the time instead of just for a week or so every year on vacation.” Jamaica has a lot of return visitors (as I’m sure every tropical destination does). And, people think they have to wait until they retire in order to make the move permanent.

I’m here to tell you – you don’t!

You can move to a tropical island and start living the life you desire NOW, not when you retire. And face it, many can’t afford to retire anyway – so why wait?

Note: This post contains affiliate links. Here’s the site’s affiliate disclosure policy for full details.

New Ecourse: How to Freelance Full-Time from the Caribbean

This brings me to my new course: How to Freelance Full-Time from the Caribbean — NOW! Of course, the info will focus primarily on Jamaica because I’ve been through the whole process here and can tell you EXACTLY what to do to make your dream a reality within a matter of months.

How to Freelance Full-Time from the CaribbeanI wrote a book about it in 2011, but I know soooooo much more now that I’ve been living here full-time since 2014. All of that knowledge will be in the course.

Literally, by next summer/fall, you could be living in Jamaica full-time if you follow the steps in this upcoming course, which will cover everything from taxes and health insurance, to getting a work permit and finding an apartment.

How to Live/Work from a “Top 5” Caribbean Destination

The course will also cover what you need to know to live/work from other destinations in the Caribbean. I’m including a “Top 5” list of Caribbean islands (what it takes to live/work there), just in case Jamaica is not for you.

Working from Abroad: Your “New Normal?”

For me, freelancing and making money online is a norm. Traveling has also always been a norm. Now living internationally is a norm. I can’t even fathom what goes on in the 9-to-5 world any longer because I’ve been doing my own thing for so long that I take my unconventional lifestyle for granted. But it’s a lifestyle anyone can have.

Many think it’s out of their reach or it’s “crazy” to freelance, and especially to freelance from a foreign country. It’s not! But …

It’s Not All Play & No Work

I put in the hours, believe me. So, I’m not saying you’re going to be able to chill out at the beach every day and party all night. You must put in the work in order to be able to enjoy the freedom this lifestyle offers.

I work many more hours for myself than I would if I worked a traditional 9-to-5, but it’s because I truly love what I do. And, the fact that I do it with an ocean view in my jammies most days is a divine bonus! 🙂

A Day at the Beach

FYI, here’s a hotel/restaurant on 7-Mile Beach (Idle Awhile). It’s where I usually go when I spend a day at the beach. Usually, I’m with the little girl that I’ve practically adopted here (I’ve known her since she was 3). We go, have lunch and just hang out for the day. They have a cheap menu, life guard, security (ie, someone to watch your bag while you swim), comfy chairs and the service is great.

A Day at the Beach in Jamaica

The #1 Thing You Need to Live & Work from the Caribbean

To live/work abroad legally in most countries, you must “bring your own job.” The exceptions are:

  • if you’re sponsored by a company;

  • if you’re married to a national of said country; and/or

  • if you have provable retirement/investment/other recurring, sustainable income.

Laws differ, of course, from country to country, but this is basically the way it’s set up. Countries don’t want you moving there without provable means of support, or having some other legal reason to be there (eg, marriage) and become a burden on their system.

BTW, there’s no “welfare” or many other social nets here in Jamaica — which shocked me. Parents pay school fees, and for books and uniforms (all Jamaican school children wear uniforms). Yeah, we’re hella lucky in the U.S.! But, I digress. Back to the exemptions from needing to bring your own job when you move abroad.

Even if you’re married, finding a job that pays what you’re accustomed to earning in the states can be close to impossible, unless you’re a highly skilled professional like a doctor, engineer, lawyer, accountant, etc. Even then though, the pay won’t equal pay in places like the U.S., Britian, Canada, etc. But, you won’t be paid a basic Jamaican wage either, which — to be honest — I don’t know how the average Jamaican makes ends meet.

FYI, I talk about Jamaican wages and finding a job in this post.

This is why freelance writing, for example, is an ideal career for those who want to live/work abroad. If you start a freelance writing business, you can register your company in the country you want to live in, then get a work permit to become an employee of your own company. Bam! You brought your own job.

I’m always running on the beach (I run marathons). This is along Negril’s infamous 7-Mile Beach.

Afternoon Run Along 7-Mile Beach, Negril Jamaica

Why I Made the Move to Jamaica Permanent for a Few Years

I’ve been coming to Jamaica since 2009. In 2014, I made the move permanent (for a few years) mainly for financial reasons, as I discuss in this post. I plan to transition back to the states in a few years. It really all depends on where I am financially and which city I can afford to comfortably move back to (Atlanta or New York).

And the reason I italicized the word comfortably is because I will not move back to the states and struggle. I want to buy a home again (preferably pay cash for it). So right now I work my patootie off and save as much as I can while living here in Jamaica, all the while enjoying the island vibe and the ease of living in a place where the attitude truly is “No problem mon.”

I’ve been all over Jamaica, but live in Negril, which is known as “The Capital of Casual.” And it truly is. I can’t remember the last time I had on a pair of heels or even put on a full face of makeup. Shorts, t-shirts, bathing suits, sundresses, sandals and flip flops are my wardrobe staples.

Home in Jamaica: View from My Balcony (Cost: Less Than $250/Mo for 270-Degree Ocean Views)

Who This Course Is Ideal For

Do any of the following sound like you? This course is perfect for those who:

  • Don’t like working a traditional 9-to-5
  • Are seeking a cheaper lifestyle
  • Are looking for a more laid-back way of living
  • Want to experience a different culture(s)
  • Want to expose their child(ren) to a different culture
  • Need to save more for retirement (or buy a home, get out of debt, etc.)
  • Want to stretch their “American” (or British, Canadian, German, Australian, etc.) dollar
  • Like to travel
  • Want “something different” out of life
  • Desire a mobile career
  • Like “fun in the sun” (duh!) 🙂

Particulars of the New “Freelance Abroad” Ecourse

Name: How to Freelance Full-Time from the Caribbean

Price: $297

Release Date: February 28, 2018

Early Bird Pricing: $47. Buy now. Expires December 31st at midnite (U.S. EST).

  • Price increases to $97 on January 1, 2018
  • $147 on Jan 15th
  • $197 on Feb 1st
  • $247 on Feb 15th, and
  • $297 on Feb 28th when it’s finally released

What Happens After You Purchase

Once you pay, you will be sent a reminder about the release date and how to enroll once the course is live. Save this info, as this course can be a tax write-off. And, if you have any questions you’d like me to answer in the course, I’ll ask you to send those along also.

Other Inkwell Editorial “Work-from-Home” Courses

Free Lifetime Access to All Courses

Remember, you get lifetime access to all material in all courses and all future updates — for free. And whenever you have questions, all you have to do is email me and I’ll get back to you. So enroll now in the course you want, and get started when you’re ready.


One person referred to the SEO Copywriting / Upwork Course Bundle as “a license to print money” — if the info in the course is put to use. (FYI, read what others are saying about the SEO writing course)

In the “How to Create Your First Ecourse” course, one student emailed me and said, “I enjoyed how much info you packed into the course and how it was only 10 or so lessons. Some of these competitors’ courses are SO LONG and involve so many “homework” assignments that I think it’s too much commitment.”

As for the relatively new “How to Make Money Writing Romance” course, I show you my sales, so you can see in black and white the potential of making money with this form of writing. And, a student DM’d me on Twitter just a week after enrolling in the course to say, “I’ve finished 2 1st drafts and working on the 3rdThey are all connected books.” So she got the info in the course, and immediately put it to use!

First-Hand Experience

All of my courses are developed and taught from first-hand experience. This means I’m able to answer any questions you have with personalized insight — which means you can succeed much quicker than I did. And that’s what it’s all about — to help you start making a living writing as quickly as possible.

Yes, You Can Pay with a Credit Card Using PayPal73 Ways to Make Money From Home as a Freelancer

See the section at the bottom of this page entitled, “How to Pay with PayPal Using a Credit or Debit Card WITHOUT Getting a PayPal Account” for how to do it. All it takes is the click of a button. Crazy easy!

P.S.: 73 Ways to Make Good Money “On the Go”

FYI, here are 73 ways to make money from home that would make ideal mobile careers. Go through the guide, find one (or a couple of complementary ones) that interest you. Then, get started. The sooner you have a viable business up and going, the quicker you can make your dream of living on a tropical island a reality.

P.P.S.: Save $100! Get This Life-Changing Ecourse for Just $197.

How to Freelance FT from the CaribbeanPhoto Credit/Copyright: All photos in this post were taken by me (Yuwanda Black).

Be Sociable & Share

    Speak Your Mind