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Lessons Learned

How I Left A 12-Year Career In Silicon Valley To Work On A Beach In Belize

Three months ago, Jeanna Barrett traded a beige office in San Francisco for a palapa on the Caribbean. This is how she pulled it off.

How I Left A 12-Year Career In Silicon Valley To Work On A Beach In Belize
[Photo: Wollertz via Shutterstock]

Three months ago, I worked in San Francisco as a marketing leader for a unicorn startup. I earned a salary that let me do, eat, and buy whatever I wanted. Now, I live and work from a beach in Belize, earn half of what I used to, and couldn't be happier.

Deciding It Was Time

After spending 12 years on a career path that just wasn’t the dream I'd imagined it would be when I started out on it, I knew it was time to try something else. I also knew that just making small changes probably wouldn't cut it—and that felt liberating. It opened up possibilities I hadn't considered.

So I decided to ditch my conventional San Francisco–tech lifestyle altogether and redefine what career success and happiness should look like on my own terms (and as my own boss) in paradise. I unraveled my American life and quickly built a new business so that I could pick up and live full time as an expat entrepreneur in a developing country.

Here in Belize, I’ve traded oatmeal-colored walls in a Silicon Valley office building for a table under a palapa overlooking the Caribbean Sea—with water more cerulean than any paint color could possibly capture. (If I'm waxing a little rhapsodic here, well, I'm betting you would too!) I decided I'd stop snoozing an alarm clock five days a week and instead wake up naturally to sunlight and birds at 6 a.m.

Jeanna Barrett's new office in Belize

Instead of a treadmill facing at a wall at the gym, I ride a beach cruiser to the fruit stand or bakery and swim laps in a pool midday for my lunch break. Sometimes I’ll even say to myself, "Hey it’s Tuesday, and I want to sit in an inner tube in the water all day and drink rum punches instead of open my laptop." So I do it.

I feel more balanced, stress-free, and happy than I ever did during the decade I was trying to push my way to the top. But before I could start working from paradise, I needed to move fast and make some tough choices. Here's how I managed to set up a sustainable business as an independent worker based overseas in just two months' time.

Month 1: Lay The Foundation For Your Remote Business

Decide your niche business, and market it correctly. First, decide what your remote online business will be and who your target audience is—hopefully you'll have a sense of this already based on your current skills and the role you're leaving behind. Then build your brand. Whether you’re a developer, designer, or marketer, you need to be able to answer, "Why are you different than your competition?"

I quickly assembled the necessary elements of a professional online business because I knew I needed something that would let me start immediately winning business; I’ll refine my brand once I have it off the ground. For me, the crucial pieces I needed to get my business live were:

  • Brand elements like a logo, brand colors, and images, and a PowerPoint template for professional pitches. You can hire someone affordable from Etsy or UpWork to do some of the branding essentials for you.
  • A stellar website that showcased my portfolio, past clients, and accolades. I was able to build a Squarespace website myself for roughly $400 (including hosting, Google Apps for Business, and stock photography fees).
  • Business cards I could hand out when I meet someone at the pool or a local bar. Networking with people on vacation is the same as networking with people in suits—anything can turn into a business deal. So I created high-quality branded cards to take with me to Belize using Moo.com.

Connect with everyone you know. For two months before I took off to Belize, I set up two to three lunches or meetings a week back in San Francisco. I reached out to other freelancers and entrepreneurs to gather their advice on running a business independently. I made phone calls and grabbed coffee with old coworkers to catch up. I announced my business on all of my personal social media accounts—including creating branded background headers for Twitter and LinkedIn. I hustled my ass off to talk about what I was doing, and nearly all of my first clients were built from these connections I made before ever boarding my flight.

Make your business official. To invoice your clients and get paid, you’re going to need to choose a business structure, likely either an LLC or a sole proprietorship. The U.S. Small Business Administration does a great job explaining the pros and cons to both. For me, the LLC made the most sense, and after a lot of research into online legal companies that can do the setup for you pretty painlessly, I found IncFile.com to be the best price. Then I signed up for Expensify to track my business expenses and FreshBooks to send invoices and track accounting.

Sign up for remote-work websites. Personally, at least, I’ve found the clients and work that come from freelancer marketplaces pay half as much as you’re worth, but it’s good to have some backup places to snag clients if you’re in a pinch. Some great resources to set up portfolios and find jobs are Contently, CloudPeeps.com, WeWorkRemotely.com, RemoteOK.io or WorkingNomads.com.

Month 2: Pack Up Your Home Base And Prepare To Go Remote For Good

Cancel everything. Before you go, cancel everything that’s going to silently charge you money from your previous lifestyle back home. For me, that included monthly transit passes, gym memberships, vehicle insurance, cable, food delivery, and more. You should even decide ahead of time if you’re going to keep Netflix in your new location (and find out if it’ll work!). I combed through my bank accounts for every automatic charge, finding a few I didn’t even realize I was being hit with every month.

Get traveler's health insurance: Health insurance is way more affordable in other countries. A lot of expats choose to "pay as they go," since in places like Belize it can cost only $30–$100 to get treated by a local doctor. But it’s a good idea to have emergency-evacuation traveler’s health insurance, just in case you need to be airlifted to a hospital in the United States. Geo Blue is a great option for international health insurance and peace of mind at only $150 a month.

Set up your phone for a foreign currency. You'll have a number of different options depending where you go, but most remote workers choose a combination of the following:

  • keep your cell phone in airplane mode
  • purchase an international data plan for emergencies
  • buy a cheap phone to make local calls
  • unlock your phone and get a local SIM card
  • use Skype or Google Voice to place inexpensive international calls

I got a Skype Number with a San Francisco area code, so I could give my clients a local number that rings my cell phone via Skype in Belize.

Prepare for your remote office. Chances are when you get to where you’re going, there will be fewer and more expensive options for computer and office equipment. Make sure you have an extra laptop charger, HDMI, and any other cables you'll need, rechargeable batteries for a mouse or keyboard, and—if you’re sticking to one spot as opposed to traveling around while you work—put a small flatscreen monitor in your suitcase, which can double as a TV in your new country.

It's a total whirlwind to pack up an entire life, build the foundations of a new business quickly, and hit the road as an expat entrepreneur within mere months. But once you’re paying half as much in rent—and spending less time working and more time working on your tan—you’ll wonder what took you so long.

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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