Digital Nomading With a Program: How it Works

Taylor Coil
7am: Buenos Aires. I roll over to check my phone, which lights up with unread messages. Rikesh is braving the Bolivian Consulate to try to sort out his tourist visa and will report back with results. Martin’s husband is visiting tomorrow and wants to know about the Indian restaurant a block from our apartments. Lauren’s making smoothies, “Anybody want one?” Our Remote Year family is awake. This is the second-ever group of Remote Year, a structured program for digital nomads. Traveling with a herd of 75 remote professionals to twelve countries in twelve months is a new experience for me. It still feels too good to be true. Being one of 75 selected from an applicant pool of over ten thousand as felt surreal since I received my letter of acceptance into the program.

How a Structured Program Works

From a prospective nomad’s perspective:
  1. Apply & get accepted. With over 10,000 applicants, the process isn’t just a formality.
  2. Join your team.  Getting to Montevideo, Uruguay, was up to me.
  3. Accommodation, workspace, social events & travel are included. 
  4. Work.  Just from a coworking space in Argentina, or a patio in Thailand, surrounded by a community of fellow nomads.
  5. Move on. As a group at the end of one month in each country.
Remote Year is the operations arm of our nomadic adventures and they handle all logistics. I don’t have to think about how I’m getting to Cusco or where I’m staying – I just know that it’s happening. All I have to do is show up.

Remote Year is Not a Job

Programs like Remote Year aren’t job providers, which is a common misconception. “What kind of work are you doing for Remote Year?” is a question people regularly ask. I work for Tortuga Backpacks, not Remote Year, and I found this job on my own. Acceptance into the program is just the first step – you’ve got to find a way to afford it.

The Upside to a Package Deal

Professional Network

My travel companions and I are working on very different things, from German translations, to iOS development, to management consulting. Skill sharing is rampant. If I have a finicky JavaScript issue, three web developers will flock to my side and fix my broken search bar (sorry, again, for breaking the search bar, Tortuganauts). I’ve helped several people with SEO and PPC marketing. Chrissy showed me how she builds a decision making model using public data. Lauren taught me the basics of hand lettering. The community of brilliant and skilled professionals is a huge benefit to a structured program. These people are my friends, yes, but they’re also my new professional network. We’re actively helping each other build beautiful things.

A Full Dance Card

Eryn and I were talking about dinner plans and I wanted to know if she was free that night. “I hate to be that person, but I can’t because my social calendar is full,” she told me. A funny moment, and hardly an insulting one, because all of our social calendars are full. This life is not a quiet life. Dinners are shared with friends. Weekends are spent exploring with a tribe of nomads, not navigating the aisles of Target. If you’re on your own, it’s because you’re intentionally saying no to something social because you need a break. I was a bit of a homebody in the United States, spending most evenings cooking in my apartment. But not here; not on Remote Year. The pace of life is much faster. I’m never bored.

Nomadic Training Wheels

We’re diving into the deep end of nomadism, most of us for the first time, and figuring it out together. It feels like adult summer camp, freshman year of college, and a traveling village, all in one. But actually, the deep end isn’t quite right. Remote Year handles the nitty gritty (important) details for us, like our plane tickets, where we’re staying, and how we’ll connect to the internet. The logistics are pretty seamless (though sometimes the internet drops out in the middle of a task, which makes me want to pull my hair out). I don’t have to worry about getting to Peru – I just pack my bags when I’m told to do so and know I’ll get there. I don’t have to think about it, I get to just go with the flow. I’m watching how Jason chooses our accomodations, how much time he allots for layovers in certain countries, what he pays attention to, and what he doesn’t worry about. I’m learning how to be a nomad in a very secure way.

The Downside to a Package Deal

Lack of Control

“I’ll go with the flow and let someone else handle it,” I say to myself. Half of the time, that feels great. My mental energy is free to focus on other things and I don’t have to worry about logistics. The other half of the time, I’m slightly (or not so slightly) frustrated that my life feels as though it’s in someone else’s hands. The feeling of owning your existence, of choosing where you live and work, is huge. Of course, I am still in control of my life. But if something goes wrong, if something about where I live, or work, makes me truly unhappy, I have the begrudging feeling that it’s not on me. The reflex to blame and complain kicks in whenever the workspace is loud, or our accommodations are not okay (like the time I found a used condom on my floor – not mine). I didn’t choose this workspace, but it’s the best internet in the city. I certainly didn’t choose this hotel, and I can see a nicer one a few blocks away. Blaming is not productive, and I really don’t like to complain. However, I miss the feeling that my choices are my own and the consequences are mine.

The Price Tag

Remote Year is $2,000 a month. I put down a $3,000 down payment and then bought my $1,100 one-way ticket to South America to join the program. I paid $1,250 to break the lease on my apartment and purchased approximately $1,800 of gear and supplies to support my life as a digital nomad. It’s not cheap. $2,000 is more than twice my monthly rent in Durham, North Carolina. I don’t have money left over at the end of the month. When we’re living in London in June, that $2,000 will feel like an absolute bargain. Could I live in London on that price tag? Probably not. But what about Cambodia in December? Yeah – you could absolutely travel to and live in Cambodia for less. Possibly significantly less.

Lack of Agility

The hotel is terrible, the internet keeps going out, and the workspace is so loud I can’t see straight. Unfortunately, I’ve already paid the monthly fee for my package deal. It’s a non-refundable. And, I don’t have a lot of money in my bank account to change my circumstances. Sure, in theory I could get on Airbnb and find a less disgusting place to live. I could go to a cafe every day instead of our workspace. But honestly, the cost of a daily cafe cortado in a relatively expensive city like Buenos Aires isn’t appealing. Similarly, I don’t want to spend all of my spending money on a different place to live when I know I can, begrudgingly, deal with it. Experiencing the local art, the weekend expeditions, and the dinners with friends is more important than my desire to live in comfort. Ideally, I want a little of both. Sometimes that doesn’t happen. In theory, I’m agile, but not always, in practice. Sometimes I feel trapped, stuck in a place that doesn’t serve my needs. If I shelled out money to be agile, I’d sacrifice experience. And isn’t experience half the point of travel? Note: disgusting places to live are not that common in Remote Year, at least not in my experience. Slow internet and workspace noise are the most common issues I face.

Social Burnout

Last month, I had the incredible fortune to attend Fuerza Bruta in Buenos Aires. It’s a mindblowing postmodern show. I rolled up with 50 friends (yes, 50) on a day when I was overstimulated and grumpy from too much social interaction. An evening with my Kindle and a cup of tea is what I needed, but I didn’t want to miss this show, so I went. Standing against the wall in the venue, feeling completely miserable, I tried so hard to find zen, to stop being furious with the world, to wipe the scowl off my face and enjoy the moment. Until the show started, I didn’t succeed. After the finale, when Fuerza Bruta turned into an impromptu dance party, Sam’s invitation to dance when the music started was met with a blank stare and stiff arms. Sorry, Sam, I just couldn’t. The overstimulation and frustration were my own fault because I’d said “yes” to far too many things that week and ignored the craving for solitude and peace for too many days. The fury, and attitude could have been avoided. While it’s true that I’m never bored and never without a friend, creating personal space is a choice.  At home, an evening with friends required planning and effort. During Remote Year, an evening to myself is the activity that requires planning and effort. The mindset is very different and I have to remember to make time for solitude.

Options Available for Package Deals

Remote Year

Group size: 75 Duration: 12 months Itinerary: varies, but some combination of South America, Latin America, Europe, and Asia Cost: $27,000 for the entire year. That’s broken into a $5k down-payment and $2k / month for the first 11 months. The 12th month is covered in your deposit. Fee includes:
  • Accommodation (private rooms)
  • Workspace with 24/7 internet
  • Travel between countries
  • A dedicated community manager and operations manager
  • Some activities like language classes, professional development events, concerts, city tours, etc.

The Remote Experience

Group size: 30 Duration: 4, 8, or 12 months (join the entire world trip, or just do a segment) Itinerary: Europe, Latin America, Asia. Cost: $1,750 per month + $3,000 down payment Fee includes:
  • Accommodation (private rooms)
  • Travel between countries
  • Travel to & from the first and last destinations
  • Desk space
  • A local guide
  • Travel insurance

Terminal 3

Group size: 30 Duration: 6 months Itinerary: Europe, North Africa, Asia Cost: $1,750 per month + $2,900 down payment Fee includes:
  • Accommodation
  • Travel between countries
  • Desk space
  • Language and yoga classes
  • Social & networking events
  • Travel insurance


If you’re considering dipping your toe into the lifestyle of a digital nomad, a structured program can be a great start. Pros:
  • Professional network
  • Social Life
  • Network of support
  • Logistics taken care of
There are some cons too:
  • Lack of control
  • Price tag
  • Lack of Agility
  • Social Burnout
Looking for a program?

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