It seems wonderful, at least in theory: you pack up your laptop, smartphone and camera and take the next flight to Belize, Germany or Nepal. You spend your days surfing the waves and your nights catching up on your freelance writing, web design, or whatever it is that your freelance work entails. In between jaunts through the mountains, you learn the local language and become a travel blogger, and then a journalist for an in-flight magazine like Hemispheres.

The reality is a bit different.

It’s certainly not impossible for a freelancer to work and travel abroad. Supposedly, you can work from anywhere as a freelancer, and this is what probably drew you to freelance work in the first place. Even if you only get to work from home, that beats spending 8 hours in a cubicle any day.

However, there are several issues you should be aware of before you pack your bags and set sail for the Caribbean. Knowing about these issues will help you better prepare for them, reducing your risk of frustration and loss of income.

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1. Wi-Fi is going to be spotty and/or expensive.

The United States has taken impressive strides to ensure that you receive Wi-Fi signal just about anywhere- even while camping. The same doesn’t hold true in other countries.

Likewise, while you can receive data through your smartphone for free while in the USA, that policy changes once you step outside its borders.

To save yourself from spending a small fortune on data fees, you will need to take advantage of Internet cafes, hotels and other public spaces until you are set up with your own connection. You should obtain an international SIM card for your phone from your provider; most providers offer these cards at a reduced rate compared to using your domestic SIM card with data roaming turned on.

Finally, obtain a Skype account or use Google Voice for calls to people back in the States or even in your country of residence.

2. You’ll be charged double on your taxes.

The U.S. is one the few countries that assesses you for taxes even if you are living and earning abroad for the entire year. This is one reason why some expats renounce their American citizenship- to finally get away from double taxation.

While I’m not recommending abandoning your citizenship status, you should talk to your tax professional about reducing the amount of tax you will owe to both the U.S. and your country of residence. One method may involve depositing as much of your income as possible into tax shelters such as IRAs. Some freelancers even go as far as to invest in real estate- hey, if you’re going to live somewhere for a few years, why not at least save on rent and taxes?

3. You’ll be working at odd hours.

Regardless of how much work you can finish ahead of time and send out to your clients for review, there will be a lag in response time and feedback simply because you will be several hours ahead or behind those clients. So, a looming deadline will probably result in you sitting at your desk at 2 a.m. in the morning and working with clients to publish something by the end of their day, not yours.

Another possible issue may surface when/if you start applying for work with fresh clients. Some companies aren’t too keen on working with freelancers who are 8+ hours away. You’ll have to convince new clients that you can still stay on top of your workload even if you aren’t conversing with them in real-time.

If you can take these realities in stride as the costs of freelancing abroad, you’ll do just fine. However, don’t expect to always have your nights free, or to have a regular 9 a.m.-5 p.m. schedule of work.

4. You’ll miss your freelance network.

While freelancers are, by their very natures, more solitary than typical employees, that doesn’t mean that they don’t know other freelancers and/or maintain a network of associates. As a freelancer, you probably belong to at least one in-town work organization, and you probably do attend various networking events and happy hours over the course of a year.

That changes once you’re living abroad, and especially if you don’t know the local language. Isolation and downright loneliness plague many an overseas freelancer.

To alleviate this issue, seek out and befriend members of your local expat community. In most cases, the expat community is quite friendly and will provide you with good advice on getting by in your local country. Additionally, you might even meet some prospective clients within that community.

5. You may end up doing odd jobs for money.

If your freelance clients fall through or can’t handle your revised schedule, what will you do for money? Sure, you could head back home…or you could pick up a few odd jobs to make the rent and pay for the expenses on your sweet Oceanside cabana. Along this train of thought, check out this list of jobs you can do while traveling the world. At the very least, obtain a TEFL certificate so you can teach English in exchange for some pocket money and maybe even room and board.

The Bottom Line

The ultimate dream of freelancing has typically been to travel the world while working. Realizing that dream is a bit harder, but not impossible. By preparing in advance, you’ll better anticipate which issues might surface during your travels. As a result, you’ll be better prepared to complete your work and keep your clients informed of any upcoming difficulties.

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Join the Discussion

  • SoniaJB

    I love this article. I am a freelancer myself and you are so right. It’s not that easy as some may think but it’s most definitely doable!Working odd hours? I know exactly what you are referring to. I wasn’t aware of the double taxes, though. I live in Canada and haven’t had any problems in that regard. Thanks for this article.

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