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  • Jeanmarie Steele

7 Things to Consider Before Becoming a Digital Nomad

Traveling while working has a lot of perks, from experiencing new cultures to boosting creativity. I have traveled to over 15 countries while working full-time at The Craftsman Agency and am often asked how I manage the digital nomad lifestyle. If you are considering the idea, I suggest you mull over a few things before booking that one-way ticket to Bali.


1. Understand not all traveling is vacation.

A lot of us see vacations as sacred occasions where we unplug from work and recharge. Traveling while working, however, doesn’t mean you’re on vacation. Your daily responsibilities and problems still exist whether you find pura vida in Costa Rica or the best gelato ever in Italy. Traveling is a luxury you enjoy around your job. That adventurous explorer you become on vacation still has tight deadlines to meet, relationships to build, and client meetings to lead.


2. Test when and how you work best.

Working remotely isn’t for everyone. The easiest way to see if you enjoy working while traveling is to do a trial run by working remotely during a vacation. It’s a low-risk experiment worth doing. My first test was working while skiing in Colorado. Rather than taking all my PTO in one go, I proposed a plan for my two-week trip that incorporated some time off, adjusted available hours, and potential risks that my manager agreed to (youdabest Molly). I quickly learned that I needed to upgrade my phone’s data plan for tethering in case Wi-Fi isn’t great, I have a three-hour threshold for working in a noisy coffee shop, and Aspen skiing is awesome.

If you don’t have an upcoming trip planned, try the staycation method: pretend you are in a new city without access to your office and monitor your happiness, communication, and performance while working “remotely.”


3. Confirm that you, your manager, and your team are adaptable to a new schedule.

Just because you might enjoy working remotely doesn’t mean your team will be as enthused. Offer your manager exact hours that you will be available and stick to them. If you can test working remotely, follow up with a postmortem. Ask your manager and team for any feedback or recommendations. Your goal is to ensure that your team never notices any difference in your productivity while traveling.

Depending on your role and expected available hours, consider how your schedule will be impacted in a different time zone. I have held bi-weekly calls at 4 a.m. and hosted impromptu meetings at 11 p.m. I don’t mind these odd hours, but you might.


4. Assess potential risks and prepare for the unexpected.

It may be common sense, but it’s worth saying: Give yourself a big window when traveling between locations. Perhaps your Airbnb host will be late letting you in, or public transportation and coffee shops are closed due to a holiday, or your flight is delayed 10 hours due to weather. These unforeseen situations may be out of your control, but that’s not how your company will see it. The beauty of traveling is immersing yourself in unfamiliar cultures, and while that’s a valuable life experience, the unexpected circumstances that arise from different customs and places should be factored into your planning. (Tip: Use weekends to change cities and weeknights to visit tourist spots.)


5. Have an internet plan…and a backup internet plan.

In my experience, internet may be easy to find around the world, but reliable internet conducive to video calls or downloading big files is not. For most remote jobs, the biggest constraint to working abroad is finding fast, secure, and reliable Wi-Fi. It’s important to do your research as well as come up with a Plan B. For example, my backup plan in Switzerland was a pocket-size rented personal hotspot; in Bali, a SIM card with a large data plan for tethering. My backups have saved me more than I can count, especially when I was working during local business off hours.


6. Consider a membership at a coworking office.

Joining a coworking space is a great way to work and travel. Most coworking spaces offer flexible memberships, such as a few hours for a desk to monthly dedicated offices. Plus, they usually have office supplies, phone booths, coffee, and hosted events to meet and network with other members.


7. Pack duplicate chargers, headphones, and converters.

Depending on where you are going, it’s worth researching if you can replace necessary work equipment like a charger or computer battery. If I am traveling somewhere remote like Patagonia, I will pack two of everything, just in case. If I plan to plant some roots in a city like Berlin, I skip duplicate chargers and make room for more clothes.


Plan smart. Work hard. You have a lot to consider when preparing to travel and work remotely, but in my experience, it’s all been worth it. Your travel dreams are a reality, and accepting that reality is a successful first step. With some research, planning, and flexibility, you can be on an island in Croatia concepting animated illustrations for an upcoming film. I like to tell people that I work remotely and travel as a hobby because work is work, no matter where I am.


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