How I Found Remote Work and Built a Life in St. Lucia
People often ask me two questions: “How did you end up living in St. Lucia?” and “How did you find a job that lets you work remotely?”
The answers are actually connected. And while my journey wasn’t exactly conventional, it taught me quite a bit about creating a life that works for you rather than building your life around your work.
So, grab a cup of coffee (or something tropical!), and let me tell you how it happened.
Sometimes Life Gives You a Reason to Make a Change
My journey began after surviving a violent attack that nearly took my life.
It was a turning point. I knew I needed to make some significant changes, and one of those was finding somewhere I could feel safe, peaceful, and genuinely happy again.
Six months later, I visited St. Lucia.
I’d traveled to 28 countries over the years, but something about this little Caribbean island felt different. The people, the natural beauty, the pace of life…it just felt right.
But I wasn’t about to pack everything up based on a nice vacation!
I spent the next 11 months researching, planning, and making several visits to experience what everyday life might actually look like here.
My final trial stay was supposed to last two months. It turned into four. 😊
By then, I was pretty confident I’d found my new home.
Of course, there was one rather important detail to figure out.
How was I going to earn a living while living on a Caribbean island?
Step One: Ask Your Current Employer
At the time, I was already working a hybrid schedule, spending part of my week in the office and part working from home.
So my first thought was pretty simple: Why not ask whether I could work entirely remotely?
I approached my employer, explained my plans, and explored whether there would be any tax or immigration complications with me working from another country.
Although she understood the arrangement could work, she still wanted someone physically in the office part of the week.
Fair enough. It wasn’t the answer I’d hoped for, but at least I’d asked.
And that’s the first piece of advice I’d give anyone interested in remote work today:
Start with the job you already have.
If your work can be done from home, there’s a possibility it can be done from somewhere else. Your employer may have restrictions based on location, taxes, security, or company policy, but it’s worth having the conversation.
You might not need to change jobs at all!
Taking the Leap Before Everything Was in Place
Here’s where I did something I wouldn’t necessarily recommend to everyone.
I moved to St. Lucia before securing my next position.
Because of the settlement from the attack and some personal savings, I had enough financial breathing room to make the move without immediately having another job lined up.
More importantly, I needed to get away from the environment I’d been living in and give myself the space to heal.
For me, it was the right decision at the right time.
But would I recommend doing it that way today?
Probably not!
The remote-work market has changed considerably, particularly since COVID. There are more people seeking remote opportunities, and competition can be fierce.
If you’re considering relocating, my recommendation is to secure reliable remote income first.
And if you do decide to make the move before finding work, I’d suggest having at least three to six months of living expenses saved, just in case.
Financial peace of mind makes enjoying your new surroundings a whole lot easier.
How I Found My First Fully Remote Work
Once I was ready to begin looking, I turned to two familiar platforms: Indeed and Upwork.
Rather than reinventing myself professionally, I looked for opportunities that matched my existing skills and experience.
That’s how I connected with my first remote client. What started as a project became a long-term professional relationship, and more than a decade later, we still work together occasionally!
Over the years, one opportunity led to another. I’ve worked with different businesses, managed operations, built systems, and developed my own bookkeeping and business services.
The work has evolved, but the flexibility has remained.
Your first remote opportunity doesn’t have to be your forever job. It just needs to be a good place to start.
Where Would I Look for Remote Work Today?
If I were starting over, I’d still begin with the same basic approach: Identify the skills I already have and look for businesses that need them.
Here are a few places I’d consider:
- Your current employer: Still my first recommendation. You already know the business, and they already know your work.
- Indeed: Use remote-work filters and pay close attention to location requirements. Some positions advertised as remote still require you to live in a particular state or country.
- Upwork: A useful place to find freelance and contract projects. It can take time to establish yourself, but strong client relationships can lead to ongoing work.
- Professional connections: Let people know what you do and that you’re available for remote opportunities. Referrals and existing relationships can be incredibly valuable.
More recently, I’ve also been working with Micro1, a platform that connects professionals with projects involving AI training and related work.
It’s another example of how remote opportunities continue to evolve.
If you’re curious, I have a referral link you can use to explore opportunities with Micro1:
[Explore Micro1 opportunities]
Disclosure: If you join through my referral link and meet the program’s requirements, I may receive a referral commission at no additional cost to you.
As with any opportunity, do your research, understand the requirements, and make sure the work is a good fit for your skills and circumstances. Availability and eligibility can change.
And please be cautious about remote-job scams. Legitimate opportunities shouldn’t require you to pay someone simply to get hired.
Eleven Years Later, What Have I Learned?
Working remotely from St. Lucia has been one of the best lifestyle decisions I’ve made. But that doesn’t mean every day looks like a vacation!
I still have deadlines, meetings, and client responsibilities. The difference is what happens when I close my laptop.
I can wander through the garden, check on the chickens and ducks, or relax in the gazebo with a cold drink. Not a bad way to end a workday!
Of course, making it work requires reliable internet, a comfortable workspace, and backup power for those occasional island outages. We’ve invested in all three so I can work productively without sacrificing the lifestyle I love.
And yes, it takes discipline when the swimming pool is just a few steps away! 😊
Maybe you already work remotely and simply want a change of scenery. Or perhaps you’re considering a bigger lifestyle change and want to experience island living before making the leap.
That’s part of the inspiration behind our Remote Reset experience at Roots Man Ways.
We’ve created a comfortable space here in St. Lucia where remote workers can stay connected, get their work done, and enjoy Caribbean living when the workday ends.
It’s a chance to experience a different pace of life without putting your career on hold.
And who knows? You might discover that a different view is exactly what you needed.
One Last Thought
If there’s one thing my journey has taught me, it’s that creating a different life doesn’t happen overnight.
It takes planning, a little patience, and sometimes the courage to try something new.
My path won’t be right for everyone, and that’s perfectly OK. Start where you are, explore your options, and take the steps that make sense for you.
After all, you get to decide what a fulfilling life looks like.
For me, it just happens to include a laptop, a tropical breeze, and a few chickens wandering around the garden.
Not a bad arrangement, if you ask me. 🌴
