Support Yourself While Traveling Abroad: An Entrepreneur's Guide To Work On The Road

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You’ve taken the leap. You’re moving towards freedom. Life on your terms and an office that comes with you wherever you go. Right on! Now comes the challenging bit—how to make earning a livelihood on the road fruitful and run smoothly so that you don’t end up living in a box on a street corner in Chiang Mai. So if a worldwide adventure while making money sounds appealing, heed this advice.

two girls killing it at expat life
Live the sweet life abroad and work while you travel.

10 pieces of advice if you want to work while you travel

1. Follow those who have gone before you. 

Join communities and/or follow leaders in the location independent field. No need to reinvent the wheel when these intrepid entrepreneurs have already done most of the heavy lifting for you. 

Some of the best people to have on your radar are:

Helps people with weekly tips to run a business from anywhere and provides tons of additional resources such as “Entrepreneur Workouts” for personal development to the actual tools to streamline your business

Read blogs like “The Very First Step To Building a Lifestyle Business Out of a Hobby,” and see one man’s journey to entrepreneurship in Bangkok. “I have the flexibility to pretty much do whatever I want, whenever I want,” writes Ogle in his about me section 

Cantwell decided to carry her business in a “stylish backpack” and writes that she “doesn’t deal with boring job moves.” Check out her definition of what a free range human really is and learn the steps to moving from the cage to the range

Ettenberg went from a New York City lawyer to a traveler to eating her way around the world and sharing it with others. Her World Traveler Resources are extremely useful and her book The Food Traveler’s Handbook shows that the flavors of the world aren’t only delicious, but a way to connect with local cultures

The website takes a particularly transparent approach to helping aspiring world workers. Email subscribers can actually take a look at detailed expense reports to see exactly how and where a successful global entrepreneur spends his money 

2. Make sure you have the necessary technology. 

The list could be endless with new gadgets, apps, and helpful tools coming out all the time. This is a great starting point. You will add your own objects according to your personal needs but this foundation can get anyone off to a good start. 

  • Laptop 
  • Unlocked phone to swap local SIM cards into as you move between countries
  • Skype account for client calls and as backup
  • MagicJack device for free international calls and a consistent phone number for people back home
  • Adapters & cords
  • External battery packs
  • Headphones

    3. Cover your assets!

    girl in nice
    Don't get stuck with a stolen bag or equipment.

    Make sure you have insurance on any expensive electronics—and consider installing a program like Prey in case your laptop is stolen. Read the story of Matthew from Expert Vagabond who had his laptop stolen and is currently hunting it down. He documents the mistakes he made that lead to the theft and gives updates on his hunt at the bottom of the initial story “Robbed In Panama! And It’s Not Pretty...”  Who knew that technology could help you recover a laptop stolen by hookers in Panama?

    4. Set up systems to work for you while indisposed by travel or no internet. 

    Using services like Hootsuite to pre-schedule tweets and Facebook posts, or the scheduling function in Wordpress for upcoming blog posts can save a ton of time, especially when you know you’ll be incommunicado for a while. Another great option is to hire a low-cost VA to manage some of your blog content, newsletter stuff, and even social media. 

    5. Plan around the stable times and BE HONEST. 

    Email turnaround time is very important especially if your business has an aspect of client service. Be honest if you will be off the grid for a while. This is a tricky one because it’s easy to assume that where there is internet, there is capability to have client calls, and this is often not the case. You never really know how good an internet connection is until you power up Skype or Facetime and try it live. Put a policy in place for your clients that helps them understand calls or email responsiveness might not always go according to plan, and that also clearly defines your Plan B for when that happens.

    6) Grow your tribe at local meet ups. 

    When abroad, it’s always great to connect with others abroad including both fellow travelers and expats (not necessarily the expats in last week’s clothing hanging off the bar at the beach though). The organization InterNations has entrepreneur work-togethers in cities all around the world and you can also join or set up your own Meetup when you know you’ll be in one place for a week or more.

    bike in yangshuo
    Hiking clubs, biking clubs—you name it, it's out there. 

    7) Plan for residual income. 

    It’s good to have at least one product to sell or item for which you’re an affiliate that can bring in a little cash while out sandboarding in Brazil’s Jericoacoara BUT you must, I repeat, MUST, have a promotion plan for these. Products are never a set-it-and-forget-it source of income so make sure to mention it regularly in the footer of your newsletter or website’s sidebar. Consider even scheduling a tweet a week to get it in front of new eyes. 

    Supplement your income by finding full or part time work through one of the programs on GoAbroad. Many companies need you to travel for them. Below are three examples of work programs that could be a good fit for the traveling entrepreneur. This will ensure a steady income and expand your contact list.

    8) Discipline, focus, and organization. 

    With no one looking over your shoulder and no one to report to, it’s pretty easy to let work slide. Procrastinating from one day to the next over margaritas or telling yourself you need a day to “just chill” after an 8 hour ride on a chicken bus can quickly catch up to. Your business won’t run itself. You’ve got to make sure you have planned time set aside to do your work, take client calls, or write and publish content (see number 4). If you’re not naturally disciplined or organized, find yourself an accountability partner you can check in with once a week to help stay on track.

    9) Set up systems to handle admin work. 

    Forget about trying to keep track of receipts and contracts, etc. If you don’t already have a system that manages contracts and invoices for you, time to get one. Satori is great for coaches and Harvest is great for other types of service providers. For receipts while you’re on the road, Shoeboxed is awesome. 

    girl holding globe
    Get out there and make your meaningful career + travel happen. Pro tip: Don't pack a globe.

    10) Let it slide. 

    Running your business from the road sounds like a dream but in reality, it’s just about the most unstable and uncertain “office” possible. Things won’t always work out.  You will get behind. Just let it slide. Life isn’t about perfection and efficiency. If you do your absolute best work and deliver tons of value most of the time, that’s great! You can spend the rest of your time inspiring people back home to break out of the box and live the life they’ve always dreamed of, like you.

    You're ready to work while you travel!

    Now that you know how to make the lifestyle work for you, get out and get after it. You'll be living the life that those cubicle-dwellers constantly dream of... and living it well (because #balance). Work AND play while you have meaningful adventures abroad.

    Travel for a Living—I’m Doing it, You Can Too!