What I Learned When I Quit My Job, Moved To The Caribbean, And Became My Own Boss

When Jeanna Barrett ditched her life in San Francisco to work from Belize, she initially felt anxious that she wasn’t working enough.

What I Learned When I Quit My Job, Moved To The Caribbean, And Became My Own Boss
[Photo: Flickr user Pablo Spekuljak]

A few months ago, I packed up my life in San Francisco and moved to Belize to be an expat entrepreneur. Much of my new lifestyle includes what I expected it to–a slower pace, more time to enjoy hobbies, a deeper tan, and a greater sense of community (since I’m living on a small Caribbean island) than the one I got used to in Silicon Valley.


But I’ve quickly learned, too, that living and working full-time (in my case, as a content strategist) in a developing country comes with unexpected challenges, especially for someone who’s spent over a decade living and working in a buzzing tech hub.

From navigating random power blackouts and vastly different communication tools to learning how to self-motivate while working steps from the beach, building a business in Belize has shown me there are tradeoffs between its many upsides and the comforts and routine of the American office. I spent so much energy just preparing to move out of the U.S. that I didn’t have much time to consider just how different my new surroundings would be and how my lifestyle–and my working style–might become.

Here’s what I learned in just my first month in Belize about the relative upsides and downsides to setting up your own online freelance or consulting business in a remote location.

related video: It’s Actually Pretty Easy To Work Remotely From The Caribbean

You’ll Need Self-Motivation In Spades

When you work remotely in paradise, you don’t have anyone telling you to get up and be in an office for eight hours–that’s part of the whole appeal. In my case, at least, the beach is mere steps away. So if you aren’t a great self-motivator, chances are you’ll struggle to get your work done.

The best way to combat that is to quickly establish a routine that you can stick to. For me, I keep the normalcy of a Monday through Friday workweek and spend my mornings tackling emails and knocking off high-priority items. Then I allow myself to relax and play during the hottest part of the day–usually at a palapa on the beach or swimming in the pool.


You’ll Worry You Aren’t Working Enough

If you’ve spent years in an office, working eight to 10 hours a day or more, it will feel really odd when you can get all your work done in half that time or less every day. But when your costs of living come down dramatically, it’s easy to keep your daily workload pretty short and still earn enough income to support yourself comfortably.

And that means you’ll have a lot of time to enjoy your surroundings. You just have to organize your client load and understand how much time it takes you to complete projects on your own–and when that’s no longer in an office, with a team, and punctuated by meetings and phone calls, it may take less time than you’re used to.

To keep myself on track, I look at my entire monthly client work and all the related tasks, then I divvy that up to weekly goals. I use Trello to track tasks and pace myself for the month ahead. I track my time in my FreshBooks account because I like to keep an integrated workspace with minimal tools, but Toggl is a popular time-tracking tool I know other independents who work remotely like to use.

As long as I stay within these deadlines I set myself, I don’t have to work long days. But I do have to keep reminding myself that just because I finished my day in three hours, it doesn’t mean I’m slacking off on building my business.

Basic Necessities Aren’t As Reliable

Imagine my surprise when within my first week in Belize, I spent more than 12 hours without lights, air conditioning, a phone, water, and Internet. Living in a developing country is a lot less expensive than the U.S., but you have to be flexible and understand that things don’t work exactly as they do in the U.S.


Sometimes there are scheduled and unscheduled blackouts. Sometimes Internet service will go out. Prepare for the unexpected by stocking your cupboards with candles, an extra jug of water, and dry goods you can eat without a microwave or stove. Don’t be afraid to go analog–or to have to press pause on your work for a while when you simply aren’t able to do it. Keep a pen and paper around, and download movies on a device that doesn’t require the Internet to watch them.

Going Low-Tech Can Sometimes Get You Further Than You Think

If you’re living and working in a developing country, there you’ll need to find less high-tech solutions to certain problems. In order to find my apartment in Belize, I had to locate a newsstand, buy a print newspaper, circle classified ads with a pen, and call property owners on a landline phone.

I also regularly participate in online forums–which are pretty archaic by now in the U.S. But they may be great way to stay connected to your local community. The best thing to do is simply to be patient, get curious about how the locals get stuff done, and adopt their ways quickly and with grace.

It’s Possible To Set Down Roots Even In A Tourist Location

Unless you’re keen to escape to someplace really isolated where there are few to no foreigners at all, you’ll likely find yourself working from a spot that’s frequented by at least a few tourists–if solely because there are enough resources for a digital nomad to earn a living remotely.

This comes with its own challenges, though, because if you’re staying permanently, it’s hard to find friends who don’t leave after a week, making it difficult to break into the tightly knit expat community. Try to get plugged into local volunteer opportunities immediately, through groups like Rotary International or The International Red Cross, take classes regularly at any fitness studios you can find in the area that may cater to vacationers, and show up continuously to local events.


You’ll start to notice who attends each week because they live here, not because they’re passing through. In Belize I’ve been able to make new friends quickly by volunteering at multiple NGOs and participating in weekly painting classes and cornhole tournaments.

You’ll Find Entrepreneurial Inspiration In Your New Community

Because developing countries don’t often have economies that provide widespread, full-time employment in office jobs, most of the local people own and run a business. I’ve found incredible inspiration in the entrepreneurial spirit of locals here in Belize–how they’ve started and built their businesses, how they grow them, and how businesses are passed down from generation to generation.

Tourism in the Caribbean (as throughout the developing world) can create opportunities for the local community at the same time that it can impose serious economic constraints–and you’ll find signs of this double-edged sword everywhere in varying degrees. But I’ve been amazed at the resilience and ingenuity I’ve found all around me, amid that push and pull. Pay attention, and you’ll likely catch some of the energy and ideas that drive your new community and channel that into growing your own business.

It’s Hard To Feel As Lonely, Busy, Or Stressed

I’ve found that even though I moved to another country by myself, I feel less lonely than I did in San Francisco. I’m also a lot less busy and a lot less stressed. In fact, feeling lonely, busy, and stressed was the norm for me for a while–and still is for a number of my friends and colleagues in the U.S.

A lot has been written about America’s “culture of busyness,” and about how overwork has become something of a status symbol. Whatever your take on that, it became immediately clear to me that this lifestyle is not celebrated in other cultures.


You’ll likely see the friends you make every day. When you go to dinner, people won’t complain about their workdays. And because you’re not spending long hours in the office, you’ll likely have more time in your day to fill with hobbies and activities you’ve always wanted to try. It becomes the norm to find pleasure in slowing down and filling your days with purpose outside of work.

You’ll Live Life Unattached To Your Phone–All Day Long

Expect to keep your phone off and unplug a lot more. Cell-phone use and apps may be growing around the world, but they aren’t as prevalent in some developing countries, so you may end up relying on them less. You’ll likely only have phone service at free Wi-Fi locations.

When you go to dinner, people won’t stare at their phones. You’ll start to lose the need to check Instagram, Facebook, and Twitter every day and won’t care if you miss the next meme or celebrity gossip. To be fair, this might be something you definitely would expect when you quit your job and move to the Caribbean–it was something I anticipated, and even looked forward to–but even after more than three months under my belt, it’s still by far one of the best perks.

Jeanna Barrett is the founder of First Page, a content strategy agency that works with startups and businesses to drive brand awareness and growth with content, social media, and SEO. Follow Jeanna on Twitter at @jeannabarrett.

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