Michael Hirshon
Like many millennials, Andrew Conley dreamed of seeing the world after college. So when he graduated from Indiana University in 2010 and landed his first job as a project manager at Epic Systems Inc. — a position that’s nearly 95 percent travel — he was excited to begin his new life on the road.
Each week, he packed a carry-on and jetted off to service Epic customers around the country. He was logging thousands of frequent flier miles and visiting exciting cities, but the demanding onsite work schedule didn’t leave much free time to experience the local culture.
Conley left Epic in 2013 to serve as executive director of 100state, a downtown Madison coworking space and tech-focused entrepreneurial hub. But he still had an itch to travel. So in 2015 when he heard about a new program called Remote Year, which allows participants to spend 12 months traveling the world while working their regular jobs remotely, he was intrigued by the opportunity. “To me, it sounded like 100state on wheels,” says Conley, 28. “I was really interested in that concept of exploring new ways of working and the freedoms that allow people to be remote — and taking that to the extreme.”
Conley was one of more than 25,000 people who applied for a spot in Remote Year’s inaugural cohort and was accepted along with 74 other so-called digital nomads. About half the group were freelancers and entrepreneur-types — the kind of participants Conley expected to see — but the rest came from the “normal corporate community,” he says.
Remote Year provides guidance and resources to people with traditional office jobs to help them figure out a way for them to telecommute. The participants pay $5,000 down and a monthly fee of $2,000, and Remote Year takes care of the rest — lodging, workspaces with 24/7 WiFi access, travel between destinations and community activities while on the road. Participants are free to come and go as they please.
Conley skipped the first month of the program while he wrapped up his tenure at 100state, then flew out on July 4, 2015, to meet up with the group. (Pro tip: Conley says Independence Day is a great day to find cheap flights.) For the next eight months, he explored Croatia, Slovenia, Turkey, Malaysia, Vietnam, Thailand and Japan — all while working remotely.
When Conley left the States he had a job at a startup called Townsquare, a transactional online real estate company. But the startup soon went under — a distressing turn of events, even under normal circumstances. With his planned income source gone, Conley turned to freelance web design and development to fund his travel. It was enough to keep him afloat, but he quickly learned the difficulty of juggling projects, customer expectations and time zones.
“With all the highs came a lot of lows too,” he says. He found comfort commiserating with others in the Remote Year group: “Everybody went through something like [I did].”
The experience was a bit like a study abroad program for working adults; some of Conley’s favorite moments were the meals he shared with people from other cultures. “We talked about everything — politics, how people treat each other, what does dating look like in other countries, how long do people live with their parents,” he says. “To be able to have those discussions in those settings was amazing.”
Conley learned a lot during his Remote Year. There were the tangible lessons — how he prefers to travel, how to earn a living while abroad, what types of work he prefers — but he also learned how to get over a lingering, guilty feeling that his decision to travel the world was, in some way, selfish.
“Am I just indulging myself, or am I doing something larger for other people?” Conley recalls wondering. He reconciled these worries by sharing the experience with his family and friends, encouraging them to make time to explore the world. “Travel is the best form of education,” he says. “I want to share that with people so they understand why I find it so important. Because to some extent, you have to do what you believe in and lead by example.”
