How I Ditched Cubicle Life & Became a Globe-Trotting Freelancer

Living the Dot Com Lifestyle Like John Chow (Almost)

I live the dot com lifestyle like John Chow. Well not nearly as successfully as he does, but I do ok. Do you wish you could too?

Do you sit at your desk dreaming of the day when you can quit your job, travel and/or just have more time to do what you want? When I worked a 9 to 5, I spent a lot of time daydreaming about this. I’m blessed enough to have realized this dream – and I try to share with as many as I can how truly possible this is – now – not some distant date in the future called “maybe one day.”

Before I lay out the steps of how to go about making this dream a reality, I want to give you a little background on me so you’ll understand where I’m coming from.

About Me: A Travelling Freelance Writer

I’ve been a freelance writer since 1993. And, while it’s wonderful and allows me to work from home for myself, it wasn’t enough for me. You see, I love to travel. My name is Yuwanda; I read someplace that “wanda” means to wander, so I guess I come by my love of travel honestly.

I’m only living up to the name my mama gave me (parents are oh so wise right from conception it seems). But, I digress.

Living Abroad: A Dream Comes True

In the spring of 2010, I realized a lifelong dream of living abroad – I moved to Jamaica part-time. Or, at least it was supposed to be part time. Now, I spend roughly half the year here. I’ll come to Jamaica for two to three months, then go back home to Atlanta for a few months. In between, I may visit friends in New York, where I lived for almost 20 years, or go to Europe for a few weeks.

When people ask me what I do for a living and I tell them I’m a freelance writer, many get this fascinated look on their face and usually ask something like, “Well how do you do that?”

“Exactly What Kind of Stuff Do You Write?”

As an aside, they usually think I write fiction a la Alice Walker or Toni Morrison. When I tell them that I mostly write “search engine optimized (SEO) copy for small businesses,” they give me that “eyes glazed over stare.” So, I just say that I write marketing copy to help small businesses get found on the web and leave it at that.

I also publish my own line of ebooks on how to become a freelance writer and other aspects of freelance writing and small business marketing.

I recount all of this not to brag, but so you can put what I’m about to tell you in context.

Writing Opportunities Online: It’s What’s Made My Mobile Life as a Freelancer Possible

In the fall of 2007, I discovered SEO writing. It catapulted my freelance writing business to the next level financially, allowing me to do some things that give me the freedom to live the way I live now. Once I realized that I had the wherewithal to make good money doing this type of writing, I started formulating a plan to start travelling.

6 Steps to Creating a Mobile Freelance Writing Career

Following are six things I did (that you can too!) to help me realize my dream of travelling while earning a living as a freelance writer.

1. Believe in Yourself: I start with this because, when you do something as “outrageous” as travelling and working, many who may be close to you might be skeptical. This is because most are raised to take the easy, safe road (ie, get or stick with a job – even a hated one).
The fact that you want to become a freelance writer may already have some looking at you sideways. The fact that you want to pick up and visit foreign lands while doing it will make many question your sanity.


The article, Why Americans Don’t Travel Overseas, underscores this point, citing that only 21% of Americans even have a passport. Until recently it was just 15% (now Americans are required to show a passport when going to Mexico and Canada, so many have gotten them). This article also lays out some interesting reasons why more Americans don’t pick up and get going.

So the first step is to actually ingrain in your brain that, “Yes, I can do this. I’m not crazy and it’s a good thing.”

2. Cut Spending: I moved to Jamaica almost a year before I’d planned to. I did so because an apartment in a building I wanted to be in that rarely has vacancies became available. Even though my budget was tight because I didn’t have all of my financial ducks in a row, I managed it. So get your finances in order.

As a long-time freelancer, I’m a prolific saver, so always have monies that I can access. This is a practice you should cultivate as a freelance writer as a matter of course by the way.

I own a home in the states. If you don’t own one and plan to travel without this burden, the following may not apply to you. If you do, following are some specific things you can do to cut expenses and save money.

Cut Phone Service: I switched my cell phone in the states to a less expensive plan. Once I looked at my actual usage, I was surprised to see that I was paying almost $40 more per month for services I wasn’t even using.

Cancel Car Insurance: Because I’m away for months at a time, I cancel car insurance when I’m gone (my car is paid for, so I don’t have that bill, thank goodness).

Get on Level Billing Plans Where Possible: I got on a level billing plan with my electric company, that way I knew exactly what my bill was going to be every month while I was away. As electric bills can fluctuate wildly in the states, this saved me a lot, even when I was home.

Cancel Garbage Service: As I wasn’t going to be there, I cancelled it. I use a company that I can just call when I get back in town and they start to pick up again immediately (once payment has been sent, of course).

Cancel Cable/Internet Service: This can be a bit sticky, but I discovered that my cable company usually has some type of offer running for “new” customers (most cable companies do). Hence, when I’m back home, I’m usually considered a “new” customer, which makes me eligible for specials they’re running; specials that tend to cost less than my regular monthly package.

Just by doing these things, I was able to shave almost $300/month off my regular monthly expenses.

3. Pay Down/Eliminate Debt: Piggybacking on the last point, the year before I moved to Jamaica, I paid off my student loan, several credit cards and my car. The only debt I have is my mortgage.

One thing being debt free (besides my mortgage) has taught me is that you have so much more freedom to make choices like this (eg, travelling). Most of what we charge (eg, clothes, dinners, bars) is stuff we should be paying cash for anyway.

So pay off as much debt as you can. Even if you never go further than grandma’s house down the street, the mental room you’ll create to formulate a better life for yourself is truly priceless.

Okay, I’m off my financial soapbox now.

4. Plan a “Normal” Vacation: If you’ve never travelled abroad before, I strongly suggest choosing a foreign country you think you’d like to explore – someplace you’ve always wanted to go. Then, take a normal vacation there first (eg, a week or two).

While there, research costs of living: eg, renting an apartment, WiFi service, food prices, transportation, etc. Actually visit apartments and go to the supermarket and take cabs, etc. This way, you’ll have a very good idea about not only the costs of possibly living there, but how happy you’re likely to be living there as well.

Foreign Apartment Renting Tip: Be sure to ask what’s included in the cost of rent, eg, water, electric, garbage, WiFi, does it come furnished/unfurnished, etc.

For example, here in Jamaica, in one apartment I didn’t have to pay for water, but when I rented a house, I did. Also, many apartments here in Jamaica do not come with hot water; you can buy this little contraption for between $30 to $50 to get it, so it’s no big deal.

But, it was a real shock to me when I first moved because it never occurred to me to ask if the apartment came with hot water. After all, it’s a “given” in the states.

5. “Triple Save”: Save as much as you possibly can. My advice would be to save three times as much as you think you’re going to need. I’ve met several Americans here in Jamaica who go back and forth to the states like I do, and what we all agree on is that we wished we’d saved more.

Why You Should Save at Least Three Times as Much Money as You Think You’ll Need

Why three times more?

Number one: Depending on where you live, the costs of goods and services can be more expensive than in America. For example, while (some types of) food is relatively cheap here in Jamaica, household goods that we can get in the dollar store in America can cost double or triple (eg, soap, toothpaste, feminine products, etc.) what you’re accustomed to paying.

Number two: Emergencies happen; it’s Murphy’s Law; ie, not a matter of if, but when. For example, I contracted some type of stomach virus once upon landing in Jamaica and had to go to the doctor. Between the visit and the medication I was prescribed, it was an unexpected $150. Another time, I had to have an emergency root canal – another $500.

Number three: You’re out a lot more. While rents are cheap here in Jamaica, I socialize so much more here than home – meeting friends at bars, having lunch with friends at the beach, going to reggae concerts, etc.

After all, the reason you live in a foreign country is to explore it fully. And nine times out of 10, that means being out, not home. And when you’re out, you’re going to spend money.

So, save, save, save as much as you can.

6. Choose a Portable Career: One of the reasons I’m able to travel and work is because I am a freelance writer. As long as I have an internet connection and a cell phone (which is becoming less and less necessary with web technology like Skype), I can work from anywhere.

I’ve worked from a friend’s couch in Barcelona, Spain; a friend’s dining room table in Duluth, MN; an internet café in South Beach, Miami; a Starbucks in New York City; and a hotel room in Stockholm, Sweden (it was a grey day), just to name a few places.

I work with clients all over the world (Ireland, Canada, the U.S., etc.) and most never know where I am; although if they ask, I freely tell them. But, most don’t care. All they care about is if you can meet their deadline.

How to Find Freelance Writing Jobs Online While You Travel

The internet is filled with legitimate opportunities in freelance writing – especially SEO content writing. I market for jobs via email only. Because I’ve been a freelancer for so long, I also get a lot of referrals.

$1,000 for One Article!

Here is some great insight into how to find freelance writing jobs, but how to make a lot of money writing simple web articles ($200-$1,000 or more per article).

The point I want to make is — anyone who’s committed to running a business (because you have to treat your freelance career as a business) can learn how to making a very good living while travelling the world as a freelance writer. The internet makes it 100% possible – if you’re willing to put in the work.

Here’s hoping this info gets you one step closer to the dream if this is your heart’s desire.

Yuwanda Black is a freelance writer and author who’s self-published over 20 ebooks to date. Her best-selling ebook on SEO writing entitled, How to Earn $250+/Day Writing Simple, 500-Word Articles, can be found on her website, The Authority Site on How to Start a Successful Freelance Writing Career. Follow Yuwanda on Twitter.