Working From Anywhere: Getting Started

Enjoy a Successful Workcation by Answering These 5 Questions

Part of the appeal of running an online business is the freedom from being anchored to a particular location. Another plus is that your online business can help fund your travel.

Before you strike out for a working vacation, there are a few things to plan and do for a productive and relaxing experience.

Use this guide to make sure you can reach your clients and customers, get your work done, stay on budget, and enjoy yourself while you’re working (far) away from home.

1. What does 'work from anywhere' mean to you?

'Working from anywhere' covers a range of possibilities from writing copy at the local roller rink (true story) to consulting with clients during your month in the Caribbean to roaming the globe for years while teaching online.

In this article, we’ll focus on working remotely within in your own country or abroad for a relatively short period of time. Most countries issue travel visas for up to three months, so consider that a good upper limit for getting started. If you’re interested in fully embracing the nomad-worker lifestyle — moving from country to country for months or even years while you work — you may want to take a few practice trips using these tips before you level up.

2. How will you connect with your customers or clients?

Where you go determines how you make calls and get online while you’re away from your home base.

Phone and internet access

If you’re traveling domestically, your phone and internet access shouldn’t change much, but you may want to check the strength of wireless coverage and speed of internet access with your hotel, landlord, or home-stay host before you go.

When you’re going abroad, make sure you’ll have a working phone and reliable internet.

For international voice, text, and data, you can buy an in-country access plan from your US carrier and use your existing phone and SIM card overseas. These plans aren’t cheap, though. For example, AT&T’s Passport packages range from $40 per month for 200MB of data to $120 per month for 800MB of data and voice calls priced from $1 to 35 cents per minute. If you’ll be out of WiFi hotspot range frequently or make a lot of calls, the international add-on option may not be cost-effective.

If you just want a backup plan and the cost isn’t an issue, an add-on package is an easy way to get access abroad, although it’s a good idea to find out which in-country network they partner with and confirm coverage at your destination. That’s important because in some countries, reliable cell service is limited to cities and major tourist areas. If you’re going off the beaten path, you may need to find other options.

Work-abroad author Kathleen Peddicord’s recommendation for travelers is to buy a local prepaid SIM card for your unlocked phone as soon as you arrive in your destination country in order to have a local number and inexpensive wireless service. However, with the local SIM card in your phone, your US phone number won’t work. For that reason, some work-abroad travelers follow travel writer Rick Steves’ suggestion to pick up a separate prepaid phone when they arrive or keep a separate unlocked phone just for in-country use.

For those times when you need to work on your laptop with internet access, in-country co-working spaces, coffee shops, and hotels can cover you for free or with a paid pass. HotelWiFiTest is a handy tool for checking WiFi speed and pricing at hotels worldwide. To protect your business data, it’s a good idea to use a VPN like the one that comes for free with the Opera browser.

Power supplies and reliability

Headed overseas? You may need to buy a plug adapter and maybe a voltage converter for your laptop and phone. Research power reliability before you go, too. You’re unlikely to face outages in major cities, but rural areas and less-developed locales may have power outages often enough to disrupt your work.

Time zones

If your business is based in North America and you keep regular office hours, the Caribbean and Central and South America are probably your best options for working vacations, thanks to the time zones. People can and do work abroad from Europe and Asia with clients in the US, but it takes more planning and careful management of your client’s communication expectations to pull that off.

 

3. What about emergencies?

It’s always smart to be prepared in case of a professional or personal emergency, and a little planning before you go can save you serious hassles on the road.

Professional emergency planning

Keep the customer service numbers for your web host, shipping carrier, and merchant bank with you. Upload copies of any work-related documents you create while you’re away to the cloud so you can reach them even if you lose your laptop or phone. If have employees back home, establish a reliable way to contact each other if something weird comes up. Better yet, delegate local mini-crisis management to a trusted employee before you go.

Personal preparedness

Even if you’re not leaving the country, it’s a good idea to touch base with your health insurer to learn your options if you need care while you’re traveling. Most US-based insurers cover emergency care abroad, but you’ll have to pay out of pocket up front and then file a claim.

For more coverage while you’re abroad, comparison shop travel insurance providers or use InsureMyTrip to find quotes. You may be surprised by how much inexpensive travel medical coverage is. For example, coverage for a month in Panama would cost me between $43 and $50. At that price, there’s no reason to skip coverage, especially because travel medical policies usually include medical evacuation coverage a huge savings in the unlikely event that you have a serious problem and need to get home for extended medical care.

 

4. Are your travel documents in order?

For international working vacations, you’ll need your passport and you may need a visa. Whether that’s a tourist or work visa also depends on the rules of your destination country. Benny Lewis, an online language instructor who’s been working while traveling for more than a decade, has written about how online work is tricky to categorize when you travel. In general, if you’re not earning money from clients in your destination country, you’re not 'working.' Ultimately it’s up to you to make sure you stay on the right side of the rules, so check before you go.

 

5. How will you access your money?

Between international ATM fees imposed by your bank and foreign exchange fees levied by your credit card, you can end up spending more than you expect on every transaction abroad. To avoid these fees, look for cards and accounts that don’t charge for foreign transactions and withdrawals. Nerdwallet, Kathleen Peddicord and the New York Times Charles Schwab’s checking account options for no-fee international ATM withdrawals. For credit cards, Nerdwallet offers a yearly list of the best foreign-transaction-fee-free options.

Business income is another thing to plan ahead. If your shop has a merchant account or if your clients pay you through PayPal or direct deposit, you’re already set. If your clients pay by check and you’ll be away from home for more than one billing cycle, move them to an electronic payment method before you head out.

 

Your 'workcation' can give you a much-needed change of scene, let you catch up with distant friends and family, or help you preview a place where you might like to move later -all while earning an income. By following these steps, it can be a relatively low-stress, high-reward experience that gets easier every time you take your business on the road.