1on1: Marketing pro Ashley Bernard and UX designer Alex Lash talk digital nomadism

Digital nomads — those who choose to work remotely while traveling, thanks to careers that require just a laptop and strong Wi-Fi connection — are growing in ranks: In 2018, 4.8 million Americans chose to give up a home address in favor of roaming.

The proliferation of Slack, email, Uberconference, Zoom and other tech tools, of course, allows remote teams to communicate easily. But it’s also the result of a mindset shift that in the 21st century, work looks fundamentally different than it once did, and a 9-to-5, office-based job isn’t seen as the only version of professional success. (At the same time, something like 43% of American workers are remote at least part of the time — and the amount of folks who work remotely as many as five days per week grew by 7% from 2012 to 2016.)

Ashley Bernard and Alex Lash attended the same women-in-tech conferences and knew some of the same technologists at home in Philadelphia, but they also share the experience — past and present, respectively — of digital nomadism, both moving from Philly to the Iberian Peninsula to live and work for an extended period of time.

Bernard, a digital marketing consultant who builds content for communities, spent three months in the fall of 2018 in Lisbon after visiting during a previous vacation and falling in love with the Portuguese city. She quit her job at a local digital agency and began taking on freelance clients in the months before moving, and retained one main client during her time there. The University of Pennsylvania grad moved back to Philly last December.

Lash, a UX designer with geospatial software B Corp Azavea, was preparing in September to embark on an open-ended trip starting in Madrid for two months and then weaving through the Schengen region, a spread of 26 European states that allow travelers to remain in any given country for up to 90 days without a visa. She picked this area because of its allowance for travel with Turtle, her cat. The Tyler School of Art grad will continue to work for Azavea while abroad.

When they met at Technical.ly HQ on Monday, Sept. 30, to interview each other about their respective trips, Bernard was about a year out from her time in Lisbon, and Lash was just a few weeks from embarking on her own international travel. (She left at the end of October.) Accordingly, they discussed how they each prepared, how they kept up with work (or planned to) despite the five- or six-hour time difference, and how to find community when everyone is a stranger.

We pulled out some of their best experiences and advice from their conversation. Below is a condensed and lightly edited transcript of their conversation.

###

Early plans

Technical.ly: How did you decide where to go when you started planning your trip?

Alex Lash: I’ve always been interested in travel and I have been fortunate to travel. I think I’ve always been interested in getting to see lots of different places, and ideally getting to live in [those] places for a semi-significant amount of time.

I’m going to be starting out in Spain and will live in Madrid for about two months. And then I’m going to go to Belgium for one month and then take a boat over to the U.K. to exit the Schengen region. A lot of the reason for that particular route is because I’m traveling with my cat — that’s been very interesting trying to plan around. He has had a huge voice [in where I go] by his very existence.

That at least sets me up for probably three to six months, and I have three months totally planned out. After that, I’m planning on being on the road for about a year or two years. And then I’m just going to see what happens.

Ashley Bernard: Thinking back to my nomad journey, I left for my trip a year ago and had planned it for about three months because of the 90-day visa [policy of the Schengen region]. I had quit my job maybe six months prior and started taking on freelance clients maybe four months before I left.

I knew that I wanted to go back to Portugal because I had been the year prior, on a vacation, and absolutely fell in love with Lisbon. I left for Lisbon on October 1 [2018]. I bought my one-way plane ticket on August 31. I wanted a soft landing, so I booked in the same hostel I had stayed at the first time I went, for four nights, and was just like, “All right, that’s enough. I’ll figure it out when I get there.”

Alex Lash: I think I’m more of a seat-of-my-pants type of planner as well, typically. And so the complication for me, of course, was the cat. And I knew it would be hard. I wasn’t quite as prepared for how difficult it would be to actually plan around him. That has ended up being actually a really nice guide for what I can do, because I don’t want him to be in long plane rides all the time, so I can’t really be hopping place to [faraway] place.

I’m going to continue working with Azavea. They’ve been really great about the whole thing and are totally on board and really supportive. When I first went to Azavea [about the idea of traveling while working remotely], I was like, “So yeah, I want to move. I truly don’t know where. I was hoping that maybe you might have some parameters around what’s OK.” At that time it was about five months out. [The parameters ended up being to] just try not to go somewhere there’s a 14-hour time differential.

Logistical preparation

Technical.ly: Once you had your loose plans in mind, what did you do to put them in place, logistically?

Alex Lash: I bought my tickets maybe two months ago, and got them on Google Flights. I was [searching for] a lot of the one-way, non-stop flights, and they give you a lot of options for seeing where you can go from different places. Ended up finding a flight to Spain that was really inexpensive and I figured, I always wanted to learn Spanish, so it seemed like a good opportunity to pick it up.

From there it was many road blocks to figure out: “OK, so we have to live in the Schengen region. The U.K. makes it really hard to bring an animal in, so how can I get around this and do it, obviously, legally?” There’s two boats I can take. One’s out of the Netherlands, I think, and then another one is out of Belgium.

I have a few spreadsheets. I have this long-running to-do list that I’ve been checking things off — going to the doctor and getting my checkup; applying for Global Entry, which could be useful for coming back [to the U.S.]. I’m using a different bank than I have been, and then I got a new credit card as well that doesn’t charge [ATM fees].

I’ve also been trolling digital nomad message boards and Facebook groups. That’s been hugely helpful.

Another thing that I really don’t want to do is fly too much because of environmental concerns. Obviously, if you’re not staying in one place, no matter what, there is going to kind of an environmental impact. But at the very least, I’d wanted to try to minimize it as much as possible and do trains when I can. I think the cat thing made that a little problematic. But from these three months out I’m going to try much harder to keep it to a minimum.

Working while abroad

Technical.ly: Ashley, what did your work routine look like abroad, and Alex, how do you plan to adjust your work routine to match your company’s?

Ashley Bernard: One of the things that I wanted and really got from this experience is that my ideal form of travel, especially after this experience, is solo — but also, more importantly, living in a space, and not just feeling like I’m a tourist. So it was important for me to be able to still work while I was doing this.

I was really lucky: I was working with a super flexible client. They were super supportive of me going remote. What I did was for certain days when I knew I had a check-in call with them, I would shift my working hours [to accommodate their time zone].

For the most part I really enjoyed working five hours ahead. I sometimes would wake up and think, “Hmm, I think I’ll go for a nice stroll. Or, I’ll go to the old part of town and get, like, a little egg tart. Or, there’s an exhibit I want to see. I’m going to go do that and then I’ll come back and do work.” It gave me a lot more flexibility.

Lisbon’s digital nomad community is huge. They actually have a happy hour every Thursday night. It’s one of the things I miss about living in a city where there were so many different people doing different things. I made some really great friends who were also kind of doing their own thing, working for themselves. And also through the nomad community, they would have coworking days at different coworking spots. I feel like every third storefront in Lisbon is a coworking spot now. So there would be open coworking days, and there was one group that was specifically digital marketers. That was really cool.

For those days I would work the normal hours in Lisbon, and then for days when I had my calls, I would either work normal daytime hours for me or I would shift things back, or just work the day and then take a couple hours off and then have that call and then be done.

Alex Lash: I hadn’t really worked remotely before, and [Azavea] wanted to see how it work with my team specifically, whether it was something I would long term want to keep doing. So we did a one-month trial. I was just not in the office for a month, not attending events, starting to establish some new team norms in preparation for when I left.

[Because Madrid is six hours ahead,] we’ve decided, at least at the outset, that I’m going to split my work days, so I’m going to have four hours in the morning where I’m just doing my own thing, and then in the evening I’m going to sign back on. So [my hours will be] 7 a.m. to 12, siesta, 4 to 8 p.m. in Spain.

[Azavea has] definitely had quite a few employees work remotely: We have somebody who’s been in Arizona for years, and at least a few folks have more recently started working remotely, one moved to Pittsburgh. It’s been nice knowing that they’ve done this before, so I’m not totally out in the wilderness with how is this going to work.

Finding community

Alex Lash: It sounds like you were meeting up with a lot of folks in nomad communities. What was making friends like in a totally different country?

Ashley Bernard: [At my hostel,] the first person I had a conversation with is this young Irish man named Jack. He’s like, “Where are you from?” and I’m like, “Philly.” And he says, “Whoa! I stayed in Philly last summer. I lived in West Philly.” He spent the summer at 50th and Baltimore. So we were bonding over these things and I’m like, “This feels so right that the first person I meet, my first new friend, is someone who spent the summer before literally three blocks away from [my apartment], because the world is tiny and beautiful and perfect.”

That really set the stage for making friends from that point on. I met a lot of people through the hostel I stayed at. From the jump I really put myself out there in a way that wasn’t too exhausting. One of my friends I met there, Shannon — I went on a walking tour and met this person. We hit it off. Walked around the city after the tour and then wound up going to some beautiful World Heritage Sites a couple days later.

The Facebook groups are key. One of my best friends in Lisbon I met because I didn’t realize [it was] a bank holiday. So I went on the Lisbon nomad Facebook group and I’m like, “Hey! So it’s apparently a holiday and everything’s closed! Anyone want to hang out? Maybe work with me? Maybe just go, you know, drink some wine and stuff like that?” Maybe someone will respond. Maybe not. And people did respond!

Take advantage of living in cities where the bars are open past two. Take a nap, have a long dinner, you can chill, and then you can rally and go out. It really is a thing of making yourself available and being open. Also, do a lot of the same things you would do at home — the things that you enjoy. If you’re into art exhibits, go to an art exhibit. If you want someone to go with, drop it in the nomad group for the city.

It’s like the first few weeks of school when everyone is open to friendship, [but] long term. At least, that’s what my experience was like.

It was magical. And I’m so excited for you.

Alex Lash:
Thank you!

###

Other resources:

• Formerly D.C.-based web developer Jessica Bell’s advice on working remotely
• Google Flights and Google Sheets for planning
• Letterer Katherine Conaway’s book, “The Digital Nomad Survival Guide“
• Facebook groups for digital nomads:
  • Female Digital Nomads
  • Nomad & Spice
  • Lisbon Digital Nomads