What’s Remote Year Like? Some FAQ

Arestia Rosenberg
9 min readMay 4, 2016


High up in La Paz, Bolivia, our third location, and all smiles. Photo by fellow Remote Year 3 Cousteau Derryl Carter.

Remote Year is currently accepting new applications and new programs are gearing up to welcome new remotes. I’ve had friends of friends or people that find me on the internet reach out with a ton of questions (understandably). Thinking about applying for Remote Year? I’ve culled together the most asked questions.

(Note: this is my own personal experience and the views expressed are not necessarily endorsed by Remote Year).

Q: Are you happy you are on Remote Year?

A: YES! I am so thrilled to be here. I feel lucky to be in a community with talented, globally-minded, community-oriented individuals, while we learn and grow through our year of long term travel without having to worry about the logistics to pull this off.

Q: Why did you do Remote Year versus just travel on your own?

A: I like having the community. And having the logistics done for me to allow other aspects in this experience to flourish. And I doubt my company would let me do anything like this without the prestige of being selected as 1 of 75 from out of 25,000 applications.

Q: What have the challenges been?

A: Getting work on board and understanding I can still have value sitting at a desk not in the office building was incredibly challenging. Giving up a life I built to pivot into the unknown was difficult. The massive to-do list and decisions that needed to be made during preparation for this trip was exhausting. But in the end? I was welcomed by others who went through the same journey and now we’re in it all together and can support one another through the challenges that come our way. I’m in month 3 as I write this. Month 1’s challenge was transitioning and finding the sweet spot for how much work to take on. Month 2’s challenge was finding balance between that work, play, health, social, etc. We’ll see what the subsequent months bring.

Q: How’s the internet?

A: It’s been different each month, but I can assure you — Remote Year takes internet very seriously. There can (will) be challenges in certain countries, but they work to provide solutions.

Internet on Remote Year is effectively broken down into three types. The first is office internet, where we are guaranteed “high-speed wi-fi”. The second is the internet in our apartments & hotels. The third is a catch-all for the solutions-based SIM card-based internet the company sometimes turns to.

The office internet, which we all share, was fantastic in month one, far slower than promised in month two, and exceptional here in month three. The internet varies dramatically across the different housing options, with some people unable to connect at all in month one, while others enjoyed lightning-fast speeds. Remote Year likes to measure things by the ability to take a video call. You ought to be able to do that in the offices, but don’t count on it in your apartment.

Here in month three, the company gave our entire group free SIM cards — the third form of internet — to allow us to tether our computers to the internet. So far it is unclear if that was even necessary, though it was appreciated.

But the beauty of you looking at a future program? They should have all these start-up kinks worked out.

Q: What is the mix of type of jobs people have?

A: On RY3, I’d say we have a pretty equal mix of full-time, part-time, contract/freelancer, and yes, independently wealthy (those jerks that built monthly revenue websites or sold off businesses! Just kidding, I love them and they’re brilliant).

About half a dozen people in our group were laid off or saw their roles within their companies diminished in the final days leading up to their departure. Some of those people immediately found other work, while others are still looking. I believe you need to have this worked out before you depart now…

Q: But people, like, work, right?

A: Yes, aside from those lucky ones I just mentioned, most people’s jobs here are incredibly important to them, myself included (I’m contract based currently with my previous employer at The Daily Beast and have been taking on other clients on a per project basis). We’ve even got some hardcore full-timers committed to working their home office hours, even when we get to Asia!

Q: Does the group all stay together with working and side travel, in addition to the flights to each country?

A: Remote Year (and personally, RY3’s Community Manager — Hi, Travis!) is killer when it comes to planning events. They are really wonderful about planning welcome and end of the month parties and a big networking event for us and locals called “The Junction” in addition to many other activities, like walking tours, art gallery openings, special dinners, sports games, etc. Also, Remotes plan activities, too, which is just the best. RY will sometimes plan weekends, too, but again, Remotes are great at planning this. We’ve had people plan Mendoza weekends, Patagonia trips, etc. If you are interested in planning practically any event or side trip, you’re almost guaranteed that fellow Remotes will be interested.

Remote Year also travels us all together in between countries — last time we were all on the same flight, before that we were on two huge buses. But people keep their own hours when it comes to work (see above).

Q: How do you do things like grocery shopping and laundry?

A: Remote Year actually has a global map that is great for identifying places in each city for things like this. But it’s also just like you were traveling anywhere — you figure it out! Some people had laundry service or washing machines at their first building, while I’ve sent mine out since starting. And we’re good with sharing with each other good info in terms of a great laundry place you found, a grocery store that was stellar, etc.

In months two and three dozens of us all lived in the same buildings. WhatsApp building channels developed in which we help each other out with these sorts of things. “Avoid the Chinese Restaurant a block from the office! Same-day laundry service two blocks to the right of the building. The grocery store by the office sells peanut butter!” You never have to figure these things out on your own.

Q: Are there translators for non predominantly English speaking countries?

A: Uuuuuh, kind of. We have city managers that help facilitate and if you do a tour or something, you can find an English speaker, but no, no translators travel with us. Figure it out! It’s an adventure!

Remote Year subsidized Spanish classes for our entire group in month one, which most of us took advantage of, as we were spending four months in a row in Spanish-speaking cities. Many of us kept the classes going in subsequent months. Take the classes, and go to them! It helps!

Q: Any trouble getting access to doctors / prescriptions while abroad?

A: I thankfully don’t have many medical problems, so I just did all my checkups and got any Rx I might need on the road beforehand (UTI and stomach issues, namely in my case). We had one guy that needed stitches and he went to the hospital, so any emergencies are fine. I gave up my home insurance because they were only going to cover me domestically. But GET TRAVEL INSURANCE. Remote Year will provide you with info and options once you accept.

In month two, my roommate took an expired emergency inhaler to a pharmacy and we politely just asked for help since we were moving to a super high elevation city next. The pharmacist couldn’t give him the identical medicine without a prescription, but he gave him something comparable. Manners will get you far.

Q: Let’s talk packing. How much luggage are you allowed to bring? Is it easy for you to pick up items you need along the way? What are your tips?

A: You decide! It’s just like traveling anywhere, but everyone agrees — BRING LESS. You can always pick stuff up along the way. I brought one backpack and one checked duffel and I’d say most brought the same, but a lot of people get extreme with bringing less. It’s just your comfort level. Other secrets: I made sure to pack so that all my clothes matched, so I can wear anything with anything. I’m not sure what your climate situation is like for your trip, but we’ve had a couple chilly days, so check out the weather along the way before getting started; layers are good. Leave the whites at home and just pack darks. You WILL IMMEDIATELY make a mess of yourself in whites, and nobody will even notice you are wearing the same clothes over and over. Laundry places will also charge you more if they have to wash your lights and darks seperately.

Also, there’s tons of advice on the Remote Nation Facebook Page, so once you get accepted and in the groove and RY connects you to that, you’ll find tons of advice, so don’t sweat it… yet.

Q: What about your apartment before you left? Did you store your belongings somewhere while you’re away?

A: I actually ended up giving up my apartment and selling most of my stuff and what little I kept I shipped to live in my mother’s garage. Some people have kept their places and sublet. Again, it’s comfort level.

Q: What are the accommodations like? I know each participant gets a private room but hoping for more color.

A: Some have opted to live alone and it’s mostly studio living. I opted to live with people and all shared apartments have only had 2 people each month (so 1 roommate). My apartment in BA was VERY nice and my apartment in Cordoba was fine. We’re in a hotel here and it’s fine. They don’t promise luxury, so don’t expect it. Some people have complained, but I think they expected the moon. I have heard of some scary situations in the previous Remote Years, but again, I think it’s all part of the business working out the kinks. I’ve been happy.

Remote Year says that they have a running chart/system ranking the apartments assigned to each of us throughout the year, so that as housing stock changes in each city, the great and the fair are equally distributed throughout the group. That system isn’t necessarily made transparent to the group though, and some people have felt that they have gotten the short end of the stick for three months in a row.

You end up having a different relationship with your housing while traveling the world than you do when you live in a static place though. Our apartments are often just the places we sleep and shower, for days or weeks at a time. The workspace, and the constellation of cafes, bars and restaurants around it are the places we spend most of our time. People organize Game of Thrones and Lemonade viewing parties in the apartment or lobby of the best apartment, or get a bar to play them for us (with a happy hour!). Home is where the group is, not where your clothes are.

We did have one person choose to move out of their apartment in month two in favor of an Airbnb. That situation is the exception to the rule for the most part, but must have felt particularly frustrating in a city where so many of us had gorgeous apartments.

Q: Drama?

A: Honestly, sometimes! But you get out of this what you put into it. There are eye-rolling moments, and there are times that you may want to lay low for a day or two. But far more important than the drama is the richly fertile soil that the experience provides for growing incredible friendships. You will have best friends in Remote Year by week three. By month two, with a housing & city change, you will be exposed to entirely new relationships that you hadn’t yet explored. Be open. Be positive. The rest will work itself out.

Q: I’m still working this out — What was the application process like for you? How long did it take for you to hear anything back/what were the steps you went through?

A: I can’t quite remember the timeline for me, but I think I submitted first round in mid-July and was ultimately accepted early September. There are a couple written rounds and a final skype interview. Once I was chosen, they sent us literature on how to talk to our companies if we needed to convince them to let us work remotely. Closer to the start date, we were given more information on travel and what areas of town we’d be in/accommodations, etc. We were also connected with the rest of our community.

My roommate in month two applied to RY4, was accepted two weeks later, and then was bumped up to RY3 in March when someone backed out. Applications and acceptances seem to happen on a rolling basis. The company is growing quickly, and we assume that even more groups will be launching before we finish our year.



Arestia Rosenberg

Storyteller, adventurer, connector. Freelance writer/strategist and filmmaker. Recovering digital nomad.