For $27,000 a year, Remote Year will let you take your job overseas

Key Points
  • The internet makes it easier for some developers, designers and some small business owners to work while traveling.
  • Working with teammates back home and keeping U.S. hours can be a challenge.
  • "We're really living in a new world where great work can be done from anywhere," CEO and co-founder Greg Caplan said.
Linsey Peterson at the Grand Palace in Bangkok during her Remote Year program.
Courtesy of Linsey Peterson

Linsey Peterson packed her bags in February— and her work — and moved from Minnesota to Kuala Lumpur. Since then, the 26-year-old web and app designer has called a new country home every month.

Peterson is a customer of Remote Year, a program that costs $27,000 a year and helps people satisfy their wanderlust while keeping their day jobs.

"I had never left North America before," Peterson said. "A lot of people on my trip have a similar story. We decided 'let's do it, let's go all in.'"

In addition to Malaysia, Peterson has also lived in Asian cities Bangkok, Thailand; Ho Chi Minh City, Vietnam; and Phnom Penh, Cambodia. In Europe, she's lived in Belgrade, Serbia, and Lisbon, Portugal, and will reside in two more cities on the continent before spending four months in South America.

The cost includes accommodations in 12 countries, travel expenses, a workspace with internet, and certain activities.

Remote Year CEO Greg Caplan came up with the idea after becoming frustrated at a 9-to-5 job. He previously founded oBaz, a fashion company that was acquired by Groupon in 2013.

"I felt stuck," Caplan said. "I wanted more. I started looking for people to go on a year journey with me."

Greg Caplan
Courtesy of Remote Year

None of Caplan's friends had the time to take a year off work, so he posed the question online. Within the first day, he had 1,000 applicants.

In total, 25,000 people applied for the first Remote Year program in 2015. Caplan and his team ended up selecting 75 people and began their year-long journey in Prague that June. Last year, the company raised $12 million from investors including Highland Capital Partners and Flybridge Capital Partners.

To date, Remote Year has accommodated 1,000 people from 40 different countries. The average age is 32, but applicants have been as old as 71.

Applicants must be employed, and Remote Year seeks a diverse set of people that the company believes will be successful working on the road for a year. Most of Remote Year's participants work in marketing, though other professions include developers, designers, lawyers, accountants and journalists, and there are also small business owners and freelancers.

"We're really living in a new world where great work can be done from anywhere," Caplan said. "In the future, having a flexible work style will give a company a strong competitive advantage."

Have job, will travel

Peterson first heard about Remote Year on Product Hunt, a site that curates interesting products, with a focus on tech. She had been working full-time for a small digital studio at the time. Peterson's company embraced her choice to work remotely, and she found someone to sublease her apartment in Minneapolis.

While in Asia, Peterson stayed primarily in private hotel rooms, and in Europe it's been mostly home rentals. She's currently rooming with five other women and said it "feels like college again."

Remote Year also plans cultural experiences like traditional cooking classes, local food and drink trips and language courses.

"One thing I was looking forward to is the community," Peterson said. "It's been really amazing to travel with the same 60 or so people place to place because of the connections you make and the connections you build."

A Remote Year workspace in Lima, Peru.
Courtesy of Remote Year

Still, there are difficulties being so far away. Many people in Peterson's program had to work specific U.S. hours. Remote Year does offer itineraries that avoid Asian countries because of time zone issues.

"The challenge was feeling distant," Peterson said. "I learned really quickly it took a lot more effort for me to communicate."

Since the start of the program, Peterson transitioned to freelance design work in order to have more travel time. Participants can also use the travel to help them build their client base.

Peterson said she is happy with the experience even though it was a big investment, and she's certain she wants to keep traveling.

"It's a really cool experience you get to do it with other people that have a similar mindset as you," Peterson said. "It taught me how to travel on my own in the future."