How One Writer Packed Her Bags and Took Off for a Year as a Digital Nomad

It’s 6 a.m. in Sydney, Australia, and I can hear the waves crashing outside the window of my un-air conditioned Airbnb. In a few minutes, the sun will rise over the ocean across the street, but I'm going to have to miss it. Instead, I'm battling heavy eyelids while I respond to urgent messages from my editor back in New York about a fast-approaching deadline. My friend sits on the floor next to me, explaining in a hushed voice to a client in Chicago that she can't hop on a video call because it is the middle of the night (and she is in her pajamas).

My work day started four hours ago, after a full day of traveling and touring. I have another hour before my shift ends. But when it does, I’ll grab a coffee, then head to the beach to take my first ever surf lesson. By tomorrow night, I'll be heading to Melbourne for the next leg of my trip. I have three stories due before midnight, and no idea when (or where) I’m going to sleep. But this is exactly what I signed up for, and every tired, cranky, over-worked minute has been worth it—even the ones that require being awake for the sunrise and missing it anyway.

After all: This is not vacation.

For the next 12 months, I’ll be living and working remotely in 12 different cities around the world through an organization called Remote Year.

WANDERLUST SETS IN

As a freelance writer, I spent much of the last two years hunched over my laptop in my tiny New York City apartment, writing stories I didn't believe in. Bored, lonely, and terribly uninspired, I'd scroll through Instagram and envy those who were bold enough to live the adventurous life that I wanted: climbing mountains, swimming with sharks, and lounging on beaches with names I couldn't pronounce. I’d always dreamed of packing a suitcase and buying a one-way ticket to the other side of the planet, but year after year I found some excuse—a job, a boyfriend, a lease—to stay right where I was.

So it's kind of perfect that it was on Instagram that I first stumbled upon Remote Year. "Become a digital nomad!" the ad beckoned. I clicked.

Remote Year, I came to learn, is basically a study abroad program for grownups. It hosts groups of approximately 75 remote workers who work and travel together, living in a new country each month for an entire year. You pay the company $2000 per month (plus an initial deposit), and they provide accommodations, travel arrangements, and co-working spaces (or at least a strong Wi-Fi signal). Working, the company makes clear, is a key part of its mission.

According to a Bentley University survey from 2014, the year Remote Year CEO Greg Caplan launched his company, 77 percent of Millennial workers believed that flexible work hours would make them more productive. And according to job search site FlexJobs (which may, admittedly, be biased on the topic), 85 percent of Millennials want to telecommute 100 percent of the time. Pair that with Airbnb's 2016 Millennial travel report [PDF], which found that 70 percent of Millennials who feel they do not have enough time to travel would travel more if they could, and you've got quite the market for a program like Remote Year.

The numbers back this up: According to Remote Year, over 25,000 people applied for 75 spots on the inaugural trip. So, sending in my application two years later, I figured there was no chance I was ever going to be selected. I didn’t even tell my mom (or my boyfriend) that I'd applied.

But a $50 deposit and Skype interview later, I was in.

PREPARE FOR TAKEOFF

After I received my acceptance email, I had exactly 75 days to sublet my apartment and pack my life into a 40-pound suitcase. But first, I had to convince my employers that I could make a remote working situation, well, work.

Even if you're not jetting off for a year-long trip (maybe you want to work from home one day per week to cut back on commuting time, or switch to a night shift to complement your spouse's schedule), approaching your boss about flexible hours or telecommuting can be daunting. In order to get the green light, you'll need to present an appropriate, feasible plan to your manager, as well as a willingness to adapt. The last thing you want, after all, is for your unique arrangements to make their job more difficult. 

For me, this meant telling my editors I'd "do anything to make it work" (and meaning it), and committing to working U.S. hours—which, for my first stop, means working from 11 p.m. to 7 a.m. local time.

Less than three months after I received my acceptance I had everything squared away, and I boarded my flight to Kuala Lumpur.

FIRST STOP, MALAYSIA

My Remote Year group, the ninth to set out, will spend the first four months of our journey in Asia, followed by four months in Europe, and four months in South America.

The big question is: What do I want to get out of this? When this year is over, I want to have a better sense of who I am and more clarity about what I want in my life, personally and professionally. I want to meet people who will push me, and learn about the world outside of the teeny, tiny existence I’ve been living for 25 years. I know I’m going to be challenged in a lot of ways, some that I can predict—like figuring out how to hold down a job with a 13-hour time difference, and learning how to manage living with 75 other people—and others that I won’t see coming. And as I move to each new location and tackle each new obstacle, I'll share what I learn with you at mental_floss. Because you don't need to buy a one-way ticket in order to change your life; that's just my story.