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So you’re looking to work remotely and travel. Congratulations, this is the first step towards ultimate work-life balance bliss! Making the leap into working from home (or anywhere with a wi-fi connection) full time is a major investment in planning out your life.

Young professionals are changing the way companies employ at all levels, and the broadest level it’s happening on is in entry-level positions. Some companies want to take a trial period before committing to employing a full-time remote team. The good news is that this gives you an opportunity to prove yourself immediately and proliferate with trustworthy companies. Over the next several weeks we will be releasing everything from our favorite travel accessories, travel tips and general thoughts to help make your remote work experience that much better! Whether you just want to tour your local coffee scene hopping back and forth from internet cafés or you want to work while on vacation in Costa Rica.

1. Initial thoughts:

What is your goal? Are you merely trying to work while on a 1-2 week vacation or are you looking to move day to day life to a foreign destination? Maybe you’re like me and you’d like to skip the daily commute while still getting fresh experience in tech? In any case, establish what you’re looking to accomplish. On a personal note, be sure to ask yourself, ‘why do I want to do this?’ Even though working remotely is being more widely accepted, it takes a special commitment to create value outside office walls.

A friend of mine faced this dilemma last year. He’s been fortunate to travel all over the world but hadn’t spent extensive time in any one place. “I regretted not doing a study abroad program in college.” He wanted to experience managing day to day life outside of the US. With a 4-6 month open window, he ultimately decided to do Remote Year.

While there may be costs associated with going through these programs, they are a great way to network and a lot of the planning is taken care of for you (from accommodations to working spaces).

2. In addition to Remote Year, consider these other Work Travel programs:

  • Croissant is a subscription-based service that allows you to select from numerous co-working spaces at all different access levels depending on what you need. They offer workspaces in some of the biggest tech hubs in North America, South America, as well as in Europe, Australia, and even Israel. This gives you options to network, grow culturally, and work in peace wherever you roam. Speaking of roaming, going without a coworking space probably won’t be the end of the world like it was for those who were using We Roam at a point in time.
  • There are more adventurous options if you’re looking to travel most of the time, try WIFI Tribe. With more freedom to select your adventure, you get lots of control while being able to explore new places in the time frames you want while creating value for your company.
  • Hacker Paradise offers a similar option to WIFI Tribe but is a more robust option for those looking to escape the daily office grind. They even have connections to other companies that can hook you up with a fitting remote job if you don’t have one yet. One of their mottoes is, “Redefine your 9-5 (and everything else too)”. This is one of your better bets for a one-stop digital nomad shop.

3. Do I need a Visa?

If you’re going away for a longer period, depending on your destination, there may be visa requirements you may need to follow. If you’re a Canadian, US or EU citizen, most countries allow you to stay in the country your first 90 days on a tourist visa. Some countries allow indefinite or extended stays for tourists also, try checking out Travisa to find more information on specific destinations. Whether you’re going for a week or months/years at a time, its good to check on Visa requirements before you dive too deep into planning mode.

4. What about my mail?

If you’re going to be gone for months at a time and don’t want to put your mail on hold with the Post Office, and don’t want to completely unplug, be sure to get a virtual address.

Of course, while we are in the paperless era, having a digital address will allow you to access your paper mail from thousands of miles away. Whether it’s ‘Save The Dates’, Wedding Invitations, Birthday Cards, or even a note from your grandmother, you’ll be up to speed on all areas of your life. Check Out Earth Class Mail and Physical Address.

5. WI-FI:

Consider your internet access. While WI-FI access has become nearly universal, not all WI-FI connections worldwide are meant to handle extensive streaming or video conferences. You have some options that will help you make the leap from place to place while staying connected.

Options for being more WI-FI self-sufficient:

  • • You can buy local hotspots upon arrival. Most airports sell them in kiosks.
  • • Try items like this global hotspot.

6. Time Zones:

Consider the time zone difference between where you are going and where your home office and/or customers are located. This is critical for any customer-facing roles.

Consider this, when it’s noon in San Francisco, 3 pm in New York, its 3 am in Bangkok…

If you’re in a customer-facing role in the US/Canada and in a customer-facing role, Latin America is the perfect destination to stay on par with your current meeting schedule.

In fact, there’s a separate article about remote client success. That blog gives careful insight into how to prep for a vacation or period away from clients and how to make the most of your vacation after its over (hint: always write about your experiences and processes).

That’s all for now, let me know what your favorite remote working locations are by sending an email to, here at ClosedWon we are firm believers in Digital Nomadism and growing the culture around it.

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