An interview with Christine Gilbert, co-creator of the upcoming documentary “The Wireless Generation.”
Want to travel? Is work keeping you doing it? How would that change if you could work from anywhere? As we featured last week, that’s the lifestyle Christine & Drew Gilbert have crafted for themselves, and it’s the subject of their upcoming documentary The Wireless Generation that they’re funding the release of with a public-backed Kickstarter campaign, ending this Wednesday.
We managed to catch a moment with Christine to ask her about the surprises, challenges and popular misconceptions surrounding a career on the road – and how budding digital nomads might take those first few steps towards doing it themselves…
1. What’s the biggest pleasant surprise you’ve encountered in shifting to a nomadic lifestyle – something you never saw coming during the planning stages?
It came when I had my son, after about two years of being nomadic. Having two stay-at-home parents has been a gift. It’s made everything so much better. When he was little and I felt tied to him all day long, we’d just travel around and I’d carry him in a sling. If he was up all night, it was okay, we just slept in the next day. It made that first year an absolute joy – between the support of having my husband there and getting to continue to travel with a very small child – we loved it. It’s an absolute luxury that most people don’t get to experience and we made a lot of sacrifices to get it. We live frugally, we work hard on our businesses, we own very little stuff. But to us, it’s the best part of having a completely flexible lifestyle.
2. What’s the biggest misconception you’re hearing about working on the road, from people who haven’t tried it?
I think a lot of people assume that we live out of suitcases all year long. My husband and I love to travel but we get burned out on moving around and will pick a place to settle down, renting an apartment, unpacking our things, buying kitchen gadgets. We’ll spend as much time in a place until we get that “feeling” again and decide it’s time to try some new adventure. I know people who travel very hard and others who have been expats in the same place for years. It’s not so much about being a nomad, but the flexibility that comes with that, even if that means heading back home and doing something completely different. It’s about choice not necessarily how or where you travel.
3. How has filming this documentary made you feel about the nature of the traditional corporate model of working, in an office or cubicle?
Before I left my job, I worked at GE as a manager, overseeing software installs and we worked with mostly virtual teams – meaning we would install the software remotely, have all of our meetings over voice or video conference and sometimes we’d even do our training via video. GE did that because, I think, they realized that it was cheaper for them and the client. The client didn’t mind once they realized they didn’t have to pay to fly out a dozen consultants and pay for us to eat reheated eggs at the Hampton Inn.
So I came into this with a strong feeling that the only thing holding back most companies was fear. Mostly it’s managers who think they can’t manage without face-to-face time (it does take practice but you can absolutely do it). During the documentary I heard the same thing, they tried to work with their boss but it was an uphill battle and one person, a professor at a university was let go when he brought it up. Now, that’s changing. One big website the Web Worker Daily just pulled their design and said they were over-hauling it, because these concepts of “how do we communicate virtually” or “how do teams collaborate remotely” have become so normalized that it’s no longer “working online” it’s just working. The tools, even if you work in an office, have just become part of our workflow.
4. How has working while traveling, assembling your mobile office and opening your laptop in so many different places, affected your work habits?
It was a big shift for me in the beginning, but not for technical reasons – it was easy enough to get online and do my work – but for emotional ones. I was lonely in the beginning. I think for most working adults a big piece of our social interaction comes from our workplace and if you jump into working from home, you’ll find this empty spot that you used to fill with little conversations with coworkers or just having other people around. I’m not sure how long it took me to get over it, but I did try to work in cafes in the beginning – anything so I didn’t feel so disconnected. Slowly overtime I built a new network of friends, most of them online, who are there to chat with when I’m procrastinating and some of them I’ve met in real life, others I’ve just known online for years.
5. What’s the most surprising thing your research for the film uncovered?
We tried to find people who came from completely different education, career and economic backgrounds because we suspected that this wasn’t just a 20-something web designer phenomenon, it was broader than that. The surprising thing was hearing the same message over and over again, about how this lifestyle change quickly became routine, meaning it wasn’t that big of a deal. They didn’t constantly think about “working online” or travel.
Instead, in their own ways, they were talking about finding meaning in everything except their work. It shifted how they thought of themselves, their place in the world, and their priorities. You might talk to someone back home at a cocktail party about their life and they’ll say they got a new job or they might get promoted and they bought a house. Talking to these folks they were focused on these other things – learning something new like photography or surfing or yoga, where they want to volunteer next, the things they want to show their children in the world, the side projects they are working on, experiences they want to have like hiking Everest base camp or getting a Master Dive certification. They’re just as hard working and ambitious as our cocktail-hour friends from home but there is a shift from working and acquiring things to chasing meaningful experiences that was universal.
6. After speaking to so many people who have taken the same itinerant career route as you have, what do you think are the most common psychological hurdles in the way of creating a location-independent lifestyle?
Fear of what people will think of you. Fear of failing miserably and publicly. Fear of not being able to pull it off. I was petrified, myself in 2008. I got a $200,000/year job offer two weeks before I was scheduled to move to Madrid, after I had quit my GE job and my family thought I was an IDIOT when I said no. I mean, they were really just disgusted with me. I said at the time, “I’ve been working in this field for eight years now. I made a lot of money. I saved. When do I earn permission to do what I want with my life? When does it end?”
There was stunned silence at the table and I think I finished my glass of wine very quickly. It was hard to do, especially as someone who grew up in a poor family with a single mother. I was throwing away all of the sacrifices she made for me. I knew though, in my heart, I had to do it. It worked out. I was lucky. Being a writer is not the easy way to go about this, but somehow I’ve made it work. I will say this though, that tremendous fear disappeared when I landed in Madrid. My husband and I drove around on a motorbike through the city and I’ve never been so happy in my life. We ate tapas, we took photos, we traveled around and tried to learn Spanish. As much as people are afraid to do it, they have no idea that those feelings can be just as strong in the opposite direction once you make the leap: pure joy. That was my story anyway.
7. Apart from watching the film when it’s released (or seeing it ahead of release by pledging $25 or more to the campaign), what advice would you give budding digital nomads on what to do and where to go to learn the basics?
Don’t be a writer! Ha. It can take 3-5 years to break into writing, so while it seems to be the most popular path, it’s actually quite hard. I’d look for work doing practical things in the beginning like teaching English (if you don’t have a college degree you can still teach English in some countries – Vietnam is one) or working as a virtual assistant. Then I’d work on your passion project at night, whether it’s writing or photography or starting your own online business. If you’re American under 30 you can work & travel in Australia with their working holiday visa. If you’re a manual worker or you’d like to try out working on farms there are tons of opportunities with WWOOF. Bars, hostels and resorts hire lots of young people under the table during high season.
Before you do anyone of that, start living cheap now! Save everything you can, it helps to have 1-2 years of expenses to start out, especially if you’re starting a new career. If you’re already working in a remote-friendly job like IT, design, editing, etc already, then you’re in good shape. If your current boss won’t go remote, you can look for other work, even if it’s a lower salary (it’s much cheaper to live overseas than it is to live in the U.S. or other western countries). Don’t let your first no scare you off. Assume it will happen and doggedly pursue your goal until it does. It worked for everyone I interviewed (even the laid off professor who later found online teaching work for a different university before moving to Thailand).