"How I moved to South America without my team knowing"

Ever wondered what it would be like to pack your bags and laptop and work from another country? (Ever had that idea a whole lot more in 2020?) This knowledge worker did just that—bought a ticket to South America while keeping his full-time job at a large software company. He didn’t even tell his team. He got his work done well enough they never caught on. One more point in the “It doesn’t really matter where you work from” column.

Under the condition of anonymity, we talked to him about how he pulled this feat off, striking the right balance of professional and personal duties, and what he learned about the nature of work during his adventures abroad.

A few years ago, I was working in San Francisco. As a tech consultant, my job requires (or used to require) regular travel. From week to week, I wouldn’t always be able to plan what was going on. Then I was placed on a six-month project that was set up in a unique way that didn’t require me to go anywhere. 

My then-girlfriend’s work situation was flexible since she runs her own company, so there was nothing really keeping us in San Francisco. I’ve always been travel minded—besides traveling for work, I’d studied abroad and lived several places—so it just came to my mind: Why don’t we rent out our place and go somewhere else?

After I got the idea, I talked to my boss, my first-line manager, because I knew if anything came up, I’d definitely need his help. I had a few years under him, and we’d always looked out for each other, so he trusted me. He just said that if I thought I could make it work, he’d support it. I didn’t tell anyone else on my team though, nor did I tell my client. 

As a technical consultant, I do application performance, which can involve migrating data centers or moving to the cloud. A big part of my job is analyzing data and then making recommendations based on what I’ve learned. But in order to do that successfully, there's a lot of work upfront that’s less focused: coordinating people, meetings, following up with emails to clarify things. You need those interactions to collect the right data. So one thing that helped was I traveled onsite to get face time with the client before we left. That helped me get a really good idea of what they were looking for and made sure everything was warm and fuzzy—that I could do the work without any additional in-person meetings.

My wife and I chose to travel across South America, partly because of the time difference. Even though the continent spans five time zones, they were compatible enough with California. Almost every month, we’d travel to another country and just rent an Airbnb: Argentina, Bolivia, Chile, Brazil, and Peru. We liked Peru so much we stayed a little longer. If we were somewhere that was in a later time zone, we could do our own thing and hang out in the morning—go get breakfast at a cafe, walk around town, and then get back by a certain time. But there were definitely some challenges to maintaining secrecy.

One thing I hadn't planned for that came up right off the bat—my work number always went to a call-forwarding service. I could schedule myself as away during certain hours and available at others, and you could just hit a button and rotate through a couple options to find me. But when you called while I was in South America, it made a different dial tone, the same long, constant one you hear when you call Europe. Luckily, I got there a week before I was going to start working and taking client meetings, so I tested it out. I was able to get a new service that would do the call forwarding inside the US, so my clients wouldn’t hear the tone. 

We always had to be conscious of what kind of internet connection we’d have, because the speed could be really bad. We’re talking a couple of kilobits. In those cases, we’d need to plan ahead for the type of work we’d be doing and what we might need. Sometimes that meant working harder while we had good connection and pushing certain things off. But there was always the assumption we could get online, and sometimes we’d be in a small little town where we really couldn’t, so we’d have to find an internet cafe. That was probably the hardest part—just wanting to be a dependable person that teammates can reach out to and connect with but not always being totally available. 

One time, we were staying at a hotel in La Paz, Bolivia. We had really bad reception and a bad Wi-Fi signal. I was on a client call, so I went into the lobby to get better service. Then housekeeping came in and started speaking really loudly so I just ducked into another room that was left open. In cases where I really didn’t know what to do, I could just hang up. That was always a sort of last resort option.  

Technological roadblocks aside though, handling clients from somewhere else was easy for me. I’ve been working remotely since 2004, and I’m pretty good at what I do, which is why the company hired me. But while we were there, I focused on doing the job I was hired for well—not necessarily going above on beyond, so I could leave more time for adventures. It was this constant balance of getting work done while taking advantage of being in a new country with my now wife.

It’s funny, because I actually proposed to her before we went to South America. We just thought of it as this trial—a chance to experience different situations together. If we made it through the other side, it was like, okay, we're good. And we’re actually talking about doing something like that again during COVID. This morning, she sent me an article about how Barbados is opening up a special 12-month visa. We’ll see. 

Obviously, things are a little different now than they used to be in so many ways. A lot more meetings are over video (although virtual backgrounds are a fun way around that), and we have two little kids now, as well. But some things are the same. We know we’re not going to have to travel anywhere for our jobs. And if you can do your work from anywhere—like it’s worth pursuing possibilities. It's your life, and you’re more than your job. You only live once.