Expats Abroad Life Abroad

Four Months & Four Cities | The Remote Experience

Who is Jillian & why did you want to go abroad?
After working remotely for nearly three years at IBM, I was craving an experience that would take me outside of my comfort zone (as well as my 600 sq. foot apartment in Boston). I had considered relocating to a new city or switching jobs to pursue something in fitness and wellness, which is where my personal passion lies. Somewhere in the middle of this “soul searching” I came across The Remote Experience, a program that gives remote workers the opportunity to travel abroad while doing their same job. Their 4 month Europe trip seemed like just the right amount of crazy. The program arranges all of the details when it comes to travel, living and co-working arrangements. Plus, it gave me some ground to stand on when convincing my company to let me travel and work in a different timezone for several months.

That’s awesome. How did you convince your work to let you go?
Getting the final stamp of approval was still no easy task. I highly recommend finding a champion at your company (ideally someone higher up in the management chain). I put together a business case that clearly articulated the benefits of the program, for both IBM as well as for my own career development. I took it to my director first because I knew he would be a strong advocate for me given his prior international work experience. He was able to get my case in front of the right people in both legal and HR. If you’re from the corporate world like me, be ready to answer A LOT of questions when it comes to tax implications, visas, health coverage etc. Fortunately, the Remote Experience had already worked out a lot of these issues. For example, we weren’t spending longer than 90 days in one particular region of Europe so there was no need for any sort of visa or any tax implications for us or our companies. Plus, through our program fees, we were covered under a secondary form of health insurance. My director was relentless. After hearing no over 30 times, he kept pushing and was finally able to get my case approved.


That’s determination! So tell us about the program.
Then the fun began. I packed 1 very heavy suitcase, a carry on and backpack (no, I did not need the 13 pairs of shoes that I brought) and boarded my one way flight to Croatia. When I arrived, I met the 10 other “digital nomads” who I would be spending the next 4 months traveling with. Having a small group was interesting. We all became very close, very fast. It felt a bit like freshman orientation of college, it was exhilarating yet exhausting. Unfortunately, throughout the next few months, the dynamic of the group changed and tension built over time. I won’t elaborate too much on this or assign blame, but traveling with a group of very different personalities can be challenging. One of the best things that the program did do for us was setting us up with a local ambassador in each city. This person was crucial in helping us assimilate to the local culture and making us feel less like a tourist. Chiara, our wonderful ambassador in Italy, instantly welcomed us into her friend group and truly exposed us to what life is like as a local in Turin. I now consider her to be a good friend who I will remain in touch with. Westley, our ambassador in Prague, also went above and beyond to welcome us to the city that he takes so much pride in. His city guide was like our bible during our month in the Czech Republic. I am so grateful for these new relationships.

How did you do with working remotely?
Social stuff aside, I found it surprisingly easy to get my work done abroad. My manager and I agreed that I would work a modified East Coast schedule, from around 12-8pm local time each day. This was ideal. I had my mornings free to visit museums, go for a run or just sit in a piazza and people watch over a cappuccino. Once it was time to work, I would post up in a cafe, head to the coworking office or hibernate in my apartment if I really needed to avoid distractions. I was truly embodying the notion that “work is where the wifi is.”


Any final words?
Fast forward 4 months and I had lived in 4 new amazing cities, met face to face with colleagues in Milan to collaborate on a project and even managed to get a promotion in the midst of all of it. Even though the group dynamic wasn’t perfect, and there were a few minor bumps along the way with us being the Remote Experience’s inaugural trip, I would 100% do it all again if given the chance. Both professionally and personally, it was an experience that allowed me to grow in so many ways.

Read more about my travels at: www.jillianremotely.com

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