4 Considerations for Traveling Freelancers

If you do a Google image search for “digital nomad,” it becomes immediately apparent why so many people covet this lifestyle. Images of people using their laptop on tropical beaches have a strong appeal for many office dwellers. Launching a company poolside, jet-setting to exotic destinations, or working on one’s own terms is a goal worth aspiring to.

If you travel as a freelancer, you will undoubtedly find yourself in some pretty cool places. Yet, it’s not always the life of leisure and laid-back fun that you might envision. Rachel Allen, a perpetual expat and nomad, says that obtaining visas and long-term residence permits can be a Kafkaesque experience that’s not really in tune with the “spontaneous and authentic” enterprise often associated with independent living.

Adam Boalt, a serial entrepreneur and CEO of TravelVisa.com, increasingly noticed that many of his entrepreneur and freelancer friends expressed a strong desire to travel more, yet they often pass up the opportunity because the amount of prep work needed before setting off on an indefinite journey is daunting, and perhaps not worth the effort. Boalt’s new business specializes in making one aspect of traveling far more practical. By securely automating the process of obtaining visas and passports, Boalt intends to make traveling easier for a new generation.

During a recent chat with Boalt, I picked his brain for tips that traveling freelancers might find helpful before setting off to fulfill their dream of adventure and independent living and working.

1. Living

One of the most intimidating facets of living an untethered lifestyle is finding living accommodations that are right for you. Depending on how long you intend to travel and how many locations you’ll visit, there are several options. You can obviously take the more traditional route and find a short-term place to rent. But one alternative that many people have recently discovered is the idea of co-living.

Often referred to as “flexible, community-driven housing” or “dorms for adults,” co-living communities are on the rise around the globe. This is particularly appealing for those fully engaged in the gig economy, going from project to project, often without a clearly defined timetable about when each project will end.

Roam, Common, and Unsettled are just a few players in the co-living space. Boalt said the flexibility of co-living appeals to many of his freelancer friends. “The notion of not being tied to a lease and having nice place to stay is liberating for a lot of people I know,” he said. “Plus co-living is a great way to meet people when you’re in an unfamiliar place.”

2. Working

Finding freelance work while traveling is no different from finding freelance work generally. You want to always be marketing yourself, connecting with new prospects and checking in on previous clients. Thankfully, freelance platforms like Moonlighting make this a breeze.

Along those same lines, freelancers sometimes face a challenge regarding finding a place to work. Coffee shops, bookstores, and other public spaces are great options for many freelancers. And many co-living communities are perfectly equipped with great workspaces. However, many people prefer a separate and dedicated place to work.

Coworking firms such as WeWork are an excellent alternative. Like co-living, long-term leases are not required, and coworking organizations strive to offer a slew of amenities. You’ll find free coffee, conference rooms, and ample areas to find solitude when you need it.

Coworking is a cultural phenomenon that meshes well with startup, entrepreneur, and freelance mentality. “Flexibility is vital for many entrepreneurs and freelancers,” Boalt said. “Starting a new business or working for yourself requires a certain degree of pliability to achieve success.”

3. Playing

It’s important not to lose sight of one simple fact when you’re a traveling freelancer: you’re there to work. Just because you might be in a beautiful location doesn’t mean you’re on vacation. That said, it’s also important to take advantage of your new surroundings and enjoy your time when you’re not working.

Finding the right balance is vital. It goes without saying that working hard doesn’t preclude having a bit of fun. Get out and see the sites. That’s one of the reasons for becoming a traveling freelancer in the first place. This goes hand in hand with coworking and co-living communities, which regularly have happy hours, exercise classes, and even organize sightseeing excursions.

“Obviously self-discipline and motivation are important to success, especially under these circumstances,” Boalt noted. “But it’s also nice to mingle with the locals and experience the culture.”

4. Do your homework

Life as a digital nomad can be a wonderful experience. However, going into it blindly or having a cavalier attitude about the practical aspects about your work situation is never a good idea. You want to stay on top of communication, collaboration, and other things with tools like Trello, Efax, and Skype.

Also, do your homework about the places and countries where you’ll be staying. One thing to consider is getting a second passport. This can be particularly helpful if one of your passports has been stamped by a country not on good terms with another country on your itinerary. Different countries have different rules when it comes to freelancers living and working within their borders. For short stays, you’ll usually be considered a tourist. But if you stay for longer periods of time, you may need to take some extra steps. Using the expertise of travel visa and passport expediters is a surefire way to avoid common missteps.

“Understanding the travel visa requirements for many countries can be tricky,” Boalt added. “One reason I started TravelVisa.com is to simplify the process for getting travel visas. I think our technology and our collective knowledge will certainly go a long way in helping digital nomads.”

This article was originally featured in the USA Today.

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