Remote Year — Participant Advice

Katherine Conaway
A Remote Year
Published in
12 min readJul 27, 2016


Whether someone is applying or accepted, current participants are constantly pinged with the same questions. So I thought, well, don’t just be cranky, Katherine, do something helpful!

This is by no means an exhaustive list of all FAQs, but it’s a start & I will update it with helpful tips as I go. Please share it around if you find it’s a useful resource for someone interested in Remote Year.

This post (currently) includes:

  • Travel Prep
  • Technology
  • Housing
  • Health, Insurance + Fitness
  • Finances

This is a work in progress! Will add more as I can :)
Post questions in the comments below & I’ll try to add answers!

For starters — if you really don’t know what I’m talking about with this “Remote Year” business, check out my first two Q&A posts, which answer the following questions:

Your First Four Questions:

  1. What is Remote Year?
  2. Why did you say Battuta earlier?
  3. How do I follow along?
  4. How has your Remote Year been going?


Your Second Four Questions:

  1. What do you think of the group of people that were selected to travel with your RY cohort?
  2. Have the working conditions allowed you to work reasonably productively?
  3. How is the housing?
  4. If you could do it over again, would you join RY or would you simply venture off on your own?

I also previously wrote about whether Remote Year is Adult Summer Camp (from the perspective of two weeks in) and How to Stay on Remote Year (at my 5 month mark).

Most of my RY-related writing lives in my publication, A Remote Year, though some is featured on Remote Year’s publication, Go Remote, along with other participants’ posts.

Travel Prep

As with most of my advice here, this is really going to be personal to you and your situation. I don’t know your country of citizenship or your RY itinerary.

I’m a big fan of google sheets / excel for everything in my life, including organizing visa needs, my packing lists, etc.

Passports & Visas

Get a new passport, or ensure that you have mostly blank pages and plenty of time before it expires. Most countries won’t accept your passport once you get close to the last 6 months. Many visas take up whole pages.

While traveling in 2015, I used up almost an entire new passport book, so I got extra pages (no longer available now) before RY.

Visas, obviously, you’re going to have to look this up for yourself. Many European countries let US Citizens in for 90 days without a visa, for example, so it’s often not an issue. We had to get our visas for Bolivia in advance, and it required some special immunizations and paperwork. Some people had to pay an overstay fee when leaving the country.

So yes, you will have to do some research on this for your individual passport + RY countries. That research should include where you can get visas abroad as that can make life easier. I got a visa for Vietnam while in Hong Kong (though I could not get one for China there).

Mom convinced me to get these RFID sleeves for my cards + passport, which I like both for the security and easily recognizing my debit vs. cc in my wallet.


Phew! I could do a whole post on this, and have been meaning to for the past 6 months. It’ll happen eventually, and I’ll post it here when it does.

Update, here it is:

In the meantime, here are some shitty hipster flat lay photos:

Yes, I brought a LOT of stuff, but this is a year of my life and I enjoy having variety (especially after 2 years on the road already). We also have had cold + rainy + mountain climates as well as hot + beach on our RY2 itinerary, so it’s been good to have a range of nice + workout + hiking + beach clothes and gear.

I have only paid baggage fees once (thanks, London, $86), but it depends on your travel. We do a fair amount of buses — no baggage limit — and major international flights usually let you check 2 bags for free. There’s often a 23 kg limit on most flights.

On the left is my first attempt packing at home pre-RY, some of that stuff didn’t make the cut. Center is one of my packing cubes — I don’t know whether they’re necessary, but I like having it (it doubles as a way to protect my clothes from less clean drawers). On the right is my Machu Picchu camping + hiking packing—and I nailed it!

Check out Tiago’s post and TJ’s video — they both came with carry-on bags only to start RY (no longer the case), which was impressive.


At the end of the day, you’re just going to have to decide for yourself what you really need for your work. Also, each RY group’s itinerary is different, so our experience of connectivity, workspace internet, etc varies.

Remember, you’re signing up to be a digital nomad. You’ll be connected, but also traveling for an entire year — and not always in #1 first world locations (on purpose). Embrace that and try to be fladaptable when you have inevitable technology challenges.

SIM Cards

Remote Year has started to offer SIM cards for $30/month. You order in advance and pay with your monthly bill, and the SIMs are waiting for you upon arrival to the next city.

I don’t know the exact numbers for our group, but many of RY2 are doing the SIM card with RY. It’s nice to show up and get it without any hassle/work on our part. It’s not always the cheapest option available, but they do tend to do a good job of getting tether able data / hot spot.

Some people just do wifi only, but given the circumstances of working + traveling + coordinating with so many people, I like having the SIM hassle-free.

Your RY managers will have some hotspots you can check out to use as needed, but we mostly just tether from our SIMs.


Most of us use MacBooks, though there are definitely some Dells and IBMs floating around my group. Some people have both a work and a personal computer. Talk to your job about their policy on computer security and replacements.

We’ve had our solid share of broken, water damaged, and stolen laptops and phones. Some people purchased new ones where we were — but that can mean having a Spanish keyboard or paying ridiculous prices because they’re imported. Some people had repairs done locally, others even flew home to get things fixed. A few tried to have new phones shipped but that failed miserably with customs and fees — do not do that option if at all possible.

Best solution so far: if you need a replacement computer/phone, find out who is having a visitor from the US/your home country coming soon, order the device to their address, and kindly thank/repay them for bringing it to you. (If that’s not legal, then shh… I said nothing.)

I have a refurbished 13" MacBook Air that I bought in 2014 to start traveling and working remotely, and I love it. Buy all the extra Apple Care you can.

If you can manage it, bring a backup phone. I use my stepdad’s unlocked old iPhone 5 for my travel phone with my RY SIM card, but keep a backup phone locked away with my passport.


I bought Apple’s adaptor kit and don’t use anything else. My phone and Kindle charge off USB. My other devices (tablet and microphone) run off USB anyway.

My Apple kit had two plugs that work for Type C (two round pins), so I have one on my laptop charger and one on my USB charger. Type C has been the most common plug type on my RY, so it hasn’t been a hassle. (I also bought a curling iron in Uruguay that is Type C so use that when I can and otherwise don’t bother.)

In England, though, I only had the 1 weird plug attachment, so I just swapped it between my laptop and USB charger.

People do use other adaptors and just attach to their existing US plug — all the Apple chargers convert energy, so you don’t need a converter (but go ahead and triple check).


You’ll fill out a survey form when you get ready to start the program to let them know your housing preferences. I don’t know their algorithm for how they match you in which location and with which roommates.

I wrote about my housing for the first few months in my “second four questions” post and put up photos of each of my rooms. Since then, my group has also been in London at The Collective and in apartments in Prague.

Overall, I haven’t had any major housing issues, though Montevideo (month 1) was a bit of an OCD-bummer / allergy nightmare for me.

You might be on your own in hotels or apartments, or you might have roommates (including a couple). Be a good roommate. Get to know the people you’re matched with, it can be a really special part of the RY experience. My Buenos Aires apartment #squad still does family dinners together.

Clean up — you won’t always have daily/weekly hotel service. Ask your RY staff member about tipping.

Housing is between a 5–25 minute walk to the workspace.

Important note: You may not always love your room. Don’t worry, you’ll be leaving in a month! So unless it’s really a problem, just breathe and take a walk.

Regardless, RY has a ticketing system, so always put complaints / notes there so they have a record and can address any real/pressing issues quickly.



When I was prepping to start RY in January 2016, we had 3 options for RY-recommended health/travel insurance.

I chose the IMG Patriot Plan and my parents encouraged me to get all the things, so I got $0 deductible, enhanced coverage, a high max limit, etc. I bought it for 7 months initially and will extend it.

PS: with US taxes, I think you can file the 673 form with your FEIE to prove you’re out of the country and exempt from needing US health insurance coverage. Again, I’m not an expert/professional, do your own research.


I’ve been to doctors in Morocco, Bolivia, Bulgaria, and the Czech Republic. Your experience will likely be very different from at home, but so far, I’ve found the medical care to be (a) totally fine and (b) much more affordable than at home though (c) sometimes a bit unusual.

With RY, we have International SOS support, and they can help you schedule appts with English-speaking doctors.

So you may have experiences like:

  • No gowns — I walked across a doctor’s office with a sweater + socks on, but no pants or underwear because gowns and coverage are a very American principle of shyness other medical professionals aren’t concerned about. It’s a bit weird at first, but its fine.
  • I had a cold and before I knew it, a nurse at a clinic in Sofia had goop all over my face and was ultrasounding me — my sinus infection diagnosis was her saying “YUCK!” (or the Bulgarian equivalent) and handing me an rx.
  • At the end of a gyn checkup in Bulgaria, I got a printed photo of my empty womb and an explanation that there was nothing (er, no one) in it.
  • Basically, ultrasounds at every appointment, of any part of your body. I’m getting more on board with it, though.
  • No English — I’ve had to bring people to translate some pretty uncomfortable situations.
  • My dentist in Bulgaria had a diamond in his tooth — bling!


In each city, Remote Year usually recommends a couple gyms near our workspace or accommodation, but a handful of people usually also do research and will find out if they can negotiate a monthly option for people to sign up if they want. In several countries, it’s been about $50/month.

I just signed up for my first ever half-marathon, in our 11th month in Cambodia, so I’m starting to run more, mostly outside.

I also practice (and occasionally teach) yoga. When I practice, I like to do classes, so I listen to Amazing Yoga classes (I have a $15/month subscription) or use the Yoga Studio app — which is great for beginners ($4). I also got a Yogo travel mat for Remote Year, which I love. And no, I don’t get kickbacks on those links, just suggesting them because they work for me.



Keep track of your money! I am a huge nerd about spreadsheets and money tracking, and I think it makes such a big difference. I personally have to carefully track my money, but I am also intent on enjoying RY and eating all the things.

Right now, I would estimate I spend an additional $1500 on average (above RY fees of $2k/month) on everything else, including additional travel, activities, transportation, food, social, personal, medical, etc.

So assume you need about $3500/month in available funds, so probably want to be earning at least $4k/month. Not all of us are there all the time, so it can be tight and can involve lots of fun credit card management.

You have to be the judge for yourself of what you can afford, including RY and all the other activities. Watch out for FOMO and spending all the money on everything all the time, because you certainly can.

Money Access

Most US Citizens are using the Charles Schwab debit card, which I also have and find super helpful. Having the app + local SIM card means I can check my balance any time.

It refunds any ATM fees at the end of the month. And I just set up transfers from my regular Chase account into my Schwab account, which usually takes 3–5 days to be available.

Non-US citizens seem to be using Revolut, but I’ve heard mixed reviews so am not sure if that’s the best approach or not. It may be the only / best current option.

Within the group, we use Venmo (US only) and PayPal (US and non-US) to send each other money for meals etc.

Credit Cards

For international travel, I love my Chase Sapphire Preferred card. I got it in March 2015 and it’s been super handy while traveling abroad and getting benefits. Most people on my program also use this card.

No foreign transaction fees; if you meet the minimum spend you get bonuses (I’ve booked around $2000 of free travel with points); if you call, an agent immediately answers; Chase is amazingly good at recognizing what charges are mine (or not) even with my erratic travel patterns.

Also, their “Ultimate Rewards” portal often has cheap deals for travel — I got a flight from NYC through Dubai (stayed 3 nights) to Delhi for $600 on Emirates.


I have not yet filed taxes for RY, so I can’t speak to exactly how this should work. I did claim FEIE previously, but I was teaching abroad and in a somewhat different situation as an official resident of another country.

In our unofficial and non-expert opinions, we do think most US citizens should be able to claim the FEIE for Remote Year, assuming you meet the requirements, through the physical presence test.

FEIE would result in an exemption, i.e.: negative income, so you pay no/less federal income tax. Read about it yourself and talk to your accountant.

Careful! Apparently there are very strict restrictions about claiming this and being able to contribute to your IRAs. Definitely check on this beforehand.

Note: if you are freelance/self-employed (like me), you still have to pay your full 15.3% self-employment taxes.

This is a work in progress! Will add more as I can :)
Post questions in the comments below & I’ll try to add answers!

Thanks for reading!

Katherine is working remotely while she travels the world — on the road since June 2014. She’s a member of Remote Year 2 Battuta, living around the world with 75 other digital nomads from February 2016 to January 2017.

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Katherine Conaway
A Remote Year

writer. traveler. storyteller. art nerd. digital nomad. remote year alum. @williamscollege alum. texan. new yorker. &