Thinking About a “Work from Anywhere” Arrangement? Ask These Questions First

Work Hard Anywhere

Overworked professionals have always dreamed of escaping to a quiet beach. But ever since Tim Ferriss’s The 4-Hour Workweek stormed the best-seller charts a decade ago, the fantasy has shifted. Instead of sipping tiki drinks and sunbathing, the new dream is to work from the beach.

Becoming location-independent and traveling the world is more possible than ever. With the internet and a laptop, scores of professions that were once desk-bound — consulting, writing, researching, designing, and more — are now free to conduct business from around the globe. It’s a glorious vision, of course. Pecking on your laptop sounds a lot more fun when you’re overlooking the Seine, or being fanned by tropical breezes. But, as I discuss in my book Entrepreneurial You, a location-independent lifestyle is perfect for some professionals — and completely wrong for others. Here are some strategies and questions to help you determine if it suits you.

Understand how you work best. On the road, no one is going to be looking over your shoulder and keeping you on task. “If you’re good at managing your own time, and you’re productive and have discipline, you’ll be able to do [work] from anywhere,” says Natalie Sisson, author of The Suitcase Entrepreneur. “But if you need to be in one place, and you need to go into an office, or you need to be surrounded by the same people all the time, it probably won’t work for you.” Understanding how you work best is an essential first step.

Try a travel pilot. You don’t have to immediately sell all your belongings and hit the road. Jenny Blake, author of Pivot, recommends piloting both your overall enjoyment of travel and the particular location you’re thinking about. She initially visited Bali for only two days, but she loved it. “It was all about yoga and spirituality,” she says. “It was totally my scene.” Her next trip was for a month, but she knew she’d enjoy it. “You don’t have to move there for a year, cold turkey,” she says. “Maybe you take a couple of trips in the next year.”

Get your business ready. If you’re planning to work part-time or full-time during your travels and you’re in a location with easy internet access, this may not be an issue. But if Wi-Fi is patchy, or you’re planning to unplug completely for a stint, you’ll want to make sure your clients and colleagues are prepared. When I took a month off to visit India in the fall of 2011, I notified my clients nearly a year in advance. There was plenty of time to strategize around my absence, and I made sure to put backup plans into place, including scheduling a month of social media posts in advance and determining which colleagues would cover for me if clients needed assistance.

Adjust your expectations. One reason your productivity might falter on the road is a need for structure. But another is the expectations you come in with. For many of us, travel has always meant vacation. But when traveling becomes your way of life — Sisson, for instance, has visited 69 countries and lived in cities around the world — you have to embrace working hard, wherever you might find yourself. As I discussed in “The Truth Behind the 4-Hour Workweek Fantasy,” it’s easy for some people to convince themselves that they want flexibility and independence, when they actually just want to work less (while earning street cred as a location-independent entrepreneur). If you want your time abroad to be transformative — and lucrative — rather than just a vacation in disguise, it’s important to level with yourself up front.

Embrace flexibility. For better or for worse, travel is unpredictable. Inevitably, you’ll face canceled flights, hotel reservations gone awry, spotty Wi-Fi, and more. Sometimes that can lead to great adventures, but only if you aren’t so frustrated and resentful that you can’t get past it. As Sisson points out, “Tropical islands always sound so great, don’t they? But they’re usually humid; there are mosquitoes. There are always other things you don’t think about.” If you want your time working remotely to be successful, you have to be willing to adapt, and accept that you can’t control everything.

Working from the beach sounds idyllic — and for many people, it is. But it’s never going to be the optimal lifestyle choice for most professionals. Some people have kids in school, or family members to care for, or they simply don’t enjoy traveling. But even for those who are enthusiastic about the possibilities, it’s worth thinking carefully about the questions above, to ensure your new location-independent lifestyle will optimize, rather than hinder, your professional goals.


Dorie Clark is a marketing strategist and professional speaker who teaches at Duke University’s Fuqua School of Business. She is the author of , and . You can receive her free Entrepreneurial You self-assessment.



Your Turn To Talk