The Traveling Freelancer: 5 Challenges to Running a Freelance Writing Business on the Road

When writing on this subject, I often refer to the “challenges” of life as a traveling writer – about the less-than-ideal realities that come with making a living as a wordsmith in locales other people only dream about seeing even once in their lives. “Challenges?” you likely ask yourself when I have the nerve to use such a word. “Who does this guy think he’s kidding? What challenges?”

Sure, imagining a downside to complete location independence seems laughable, but like always, the vivid colors on the other side of the proverbial fence often lie, don’t they?

Note: That said, a definite caveat is that even with these so-called challenges, I wouldn’t consider trading my life for a 9 to 5 even for one second.

But to go on, a healthy dose of realism before you embark on a similar journey can help you make a sound decision before tackling the significant process of setting up your writing business and heading out on to the road. So again, what could possibly go wrong?

1. Internet Connections

Especially in places like here in Southeast Asia, internet connections provide a constant headache for someone that depends on being wired in to make a living. Even when paying good money for a connection in your room – wireless or dial-up – the only thing you can count on is not being able to count on a steady signal.

Especially, it seems, when in the middle of a huge project.

Not too much of a problem for a writer, you might think, but don’t forget the admin side of the writing biz – the need for constant communications with clients, Internet research, and uploading documents to emails, etc. Sometimes even one single email attachment can take hours.


If you enjoy working in your apartment or hotel room but log on for the day to find the internet sucks, log right back out, stuff your equipment into a daypack, and beeline for a predetermined coffee shop or Internet cafe. Seek out these dependable locations (a few of them, actually) first thing when you arrive in a new city so you always have options.

Don’t insist on sitting in front of your laptop all day, demanding webpages to load faster than they care to – yep, been there before.

In more isolated locations set further back in time, internet will be tragic if available at all. If going to an untouched paradise, get work done beforehand and let clients know you’ll be unavailable for a short period. Or, if making enough money and intent on being the most die-hard of road warriors, buy the high-tech equipment needed to stay connected anywhere.

2. Balancing Work and Play

Balancing work and play presents a unique problem for anyone working without a boss or rules and restrictions. Travelers have an even tougher job of rising to the challenge due to the amazing places we choose to live in.

You will constantly meet people who want you to come out and enjoy their vacation with them, and try as you might to control yourself, you will party until the early hours of the morning every once in a while.

Fascinating locals and foreigners alike will eat up your time if you let them.

Have your fun, but practice self-control, a necessary skill that can radically transform your life and allow you to continue enjoying the freedom your chosen path creates. You absolutely must continue penning articles and making money if you don’t plan on going home anytime soon.

Set goals for each week, and restrict playtime. Embrace the art of balance.

3. Keeping It on the Hush

Most governments in the world today have yet to figure out how to collect their money from foreigners who stay in their country but work online, though they would very much like to.

Most online businesspeople, meanwhile, don’t bother to clue them in. For the time being, these things are either ignored or overlooked, but in some countries, working on the web without a work visa (and without paying taxes) constitutes a crime.

If living in one for a long period of time, consider becoming legal if possible, but if you want to just roam, it might not be worth it as most places really do let you slip through the cracks.

Just remember you might want to fudge the facts a bit when people inquire about what you do and whether you have a work visa. There are some people out there, both expats and locals, who will envy your life, and why wouldn’t they?

Personally, I don’t always lie about what I do and have done a bit of online marketing consulting and web design here and there in the places I travel (a great skill to barter, by the way). You’ll just have to use your own judgment here, and consult with an attorney before doing as I do, of course.

4. Focus, Focus, Focus

Besides the people you meet who all want to party it up, there are countless things to see and do in some of the best international locations, and you will want to do them. Imagine looking out your bedroom window over vivid Argentinean vineyards or the sprawling Parisian metropolis and telling yourself you need to get some work done instead of exploring…


But focus is a must. Guard your time wisely, all the while reminding yourself that without a steady stream of completed work your dream will not last long. And don’t just make enough to get by – savings for a rainy day and investing in the future are double important for you due to the nature of your work and your free-wheeling life.

Implement habits that help you to keep a steady routine every day, and make productivity a major goal in your life. Sustaining such freedom ironically requires a bit of structure.

5. On the Road Again

Perpetual travelers often, you guessed it, travel. I personally like to stay put in one place for long periods of time. I settle in and get a long-stay apartment, always cheaper than nightly rooms, and get to know the place a little bit.

But even this somewhat stationary cowboy needs to run off on trips to get visa stamps, go sightseeing, or move to new locations.

Getting things done while moving around takes real planning and intentional lifestyle design. You tell yourself you’ll do some writing on the bus or get straight to work when you get there, but these things rarely happen (ironically, I’m actually on a bus to Laos while I write this, so sometimes you do fulfill your own expectations, but I must say I’m getting a little carsick).

Balance, again, is your friend.

Plan all your travels at least a week in advance (as obvious as that sounds I used to never plan even that far ahead) and arrange your work schedule accordingly.

Another unique solution is to work for five days at a time, staying in one place, and then use your weekends as transit time. Work three 10 hour days and take the rest of the week off. Or, work your butt off double-time for a month and then take the entire next month off to wander or play – remember, you’re the boss, so you make the rules here.

So as you can see, challenges to working on the road do exist-like anything else, there are downsides and upsides. But all that said, writing about the downsides here only reminds me of my good fortune, so don’t be discouraged.

There are plenty more disadvantages to getting stuck back at home, slaving away in the name of mediocrity. There are more downsides to ignoring your heart when all it wants to do is go…