Embracing the Life of a Traveling Entrepreneur

By Andrea Ditter-Middleton

The technological advances of the 21st century have brought a number of fundamental changes to modern life. You don’t have to be home at broadcast time or even have a cable subscription to watch all your favorite TV shows, and you can make phone calls and access the internet from virtually anywhere. In a similar vein, your career may no longer require pounding out 9-to-5 hours in a cubicle.

Remote working continues to grow in popularity for a number of reasons. It allows companies to recruit the best talent, no matter where they live, and it allows workers to create and maintain their own schedules, leading to greater flexibility for family activities and personal time. In fact, a growing number of today’s remote workers and entrepreneurs don’t even have a “home” at all, but travel the world while working remotely. These digital nomads are redefining the concept of work/life balance.

Becoming a Digital Nomad

Remote workers go by many names: traveling entrepreneur, digital nomad, location independent, and more. Often young professionals, they work in a number of industries, from software engineering and marketing to copywriting and graphic design. Commonly freelancers or entrepreneurs, many see the digital nomadic lifestyle as a calling. Blogger Katelyn Smith, also known as The Remote Nomad, eloquently describes the experience as “a total life transformation.” In other words, it’s not an extended vacation; it’s a lifestyle.

Understandably, embarking on the life path of the digital nomad doesn’t happen all at once. Instead, a series of events or a slow realization over time leads to this choice. For Robert O’Kruk, co-founder of the free, community-based site Digital Nomads Forum, it all began on a company trip to Mexico. After leaving home as an adult for the first time, he caught a “travel bug” that led him to book an extended solo backpacking trip to Nicaragua. It was there that he met other digital nomads who introduced him to the idea of working while traveling.

O’Kruk used the time and experience to work on his side project, Mala Forest, which gave him firsthand experience living a location independent lifestyle. Once he returned to his office job in Canada, he knew he had to make a change. “My gut told me I had to quit.” The rest, as they say, is history.

Planning a Location Independent Lifestyle

Becoming a digital nomad is not just about hating your day job and loving the beach. There’s a lot more to this path than buying a laptop and a ticket to Southeast Asia. In O’Kruk’s case, he spent months laying the groundwork for this lifestyle change. He timed his departure to coincide with the end of his apartment lease, and he sold everything he owned, from furniture to dishes.

He had to consider the logistics of planning and adapting to a new, impermanent lifestyle. This included starting another business, Digital Coalition, and increasing his load of freelance work as a marketer. He also secured proper temporary housing before departing, figured out a budget, and arranged transportation abroad.

In their recently published book “The Digital Nomad Survival Guide,” Peter Knudson and Katherine Conaway list a number of additional considerations that aspiring digital nomads must take into account, including:

  • Visas for international travel
  • Food costs
  • Medical considerations, including insurance
  • Charity and gift-giving
  • Planning for the unexpected, such as family emergencies and natural disasters

O’Kruk also adds planning for Wi-Fi access and subscribing to a VPN (Virtual Private Network) service to the list.

Key Tools of Traveling Entrepreneurs

Transitioning to the life of a digital nomad has never been easier. In fact, many common web platforms like Google Docs help traveling entrepreneurs stay safe and protected by storing photos of passports and credit cards. Sites like LastPass help manage passwords, and Skype keeps travelers connected to family and friends.

Most important, however, is finding a community and resources to help with transitioning and sustaining a location independent lifestyle. O’Kruk’s Digital Nomads Forum, for example, helps both new and experienced traveling entrepreneurs find support. In addition, using convenience-based services such as CORT Furniture Rental can save time and stress when setting up a temporary home. The ordering process is simple, and CORT takes care of everything else to make your temporary space feel like home.