What You Really Need To Know Before Starting Remote Year

It’s not about the luggage.

Jess Chiu
Jess Chiu
Jan 4, 2017 · 7 min read

Remote Year has come a long way in a pretty short time. When I was applying, I had to scour the internet for weeks to try and figure out if this program was the new-age Nigerian prince scam.

By the time I dropped thousands (which is equivalent to MILLIONS in Canadian dollars) on my deposit and bought a one-way ticket, I still wasn’t sure that someone was going to greet me in a city that I had never heard of.

It’s pronounced CÓRdoba, damnit.

Now, a simple Google search will show you that Remote Year is a legit business, and everything from their interviews to their Instagram is selling this dream life. And somehow it still seems fake.

It should.

Your radar should be pinging because these strangers are asking you to change your ENTIRE WAY OF LIVING.

So you reach out to a friend of a friend who you heard is on Remote Year, or you message a stranger on their blog, and you start asking questions. I hope this answers some of them.

Can you tell me how you became financially independent?

I quit my job and started freelancing. I’m also really lucky that I’m a cheap, cheap drunk.

Fact: I spend a lot of time looking for ramen in foreign countries.

Can you help me figure out if this is right for me?

No. Do you know how time consuming it is to find the best fried chicken in a new city every month? I’m fucking exhausted.

Plus, this is something you gotta figure out yourself. I literally took 2 flights out of a country on New Year’s Day because I was too lazy to Uber to the visa office for an extension. Am I REALLY who you want to turn to for life advice? But if you insist on an answer, mine is, “if you can, then you should.”

What luggage/supplies should I get?

By the time you’ve packed and repacked your life a million times, you’re going to curse Amazon for being so great at recommending useless shit for you to carry around. Then you’re gonna wish that shipping your crap home was cheaper and more reliable.

But really, common advice people like to give is ‘pack what you need and halve it’. I’d even go so far as recommending that you pack what you need for a week and adding a few more essentials that are long term weather dependent.

Buy everything else as you go. I PROMISE you, the rest of the world sells junk too.

Would you recommend Remote Year?

This one is hard, because based on the type of person you are, there may likely be other options that are better suited for you. If you have done any preliminary research at all, I would bet that Facebook is hardcore targeting you with half a dozen of those options every time you open your feed. Turn off your ad block and check them out.

But the Remote Year Instagram is bomb.

Hells yes. This year we’ve literally travelled around the world. But what you don’t see in a scenic mountain gram are the people who broke bones on the way up; the sheer exhaustion after 3 straight days of busses, flights, and layovers; the struggle to finish work when it’s 6am and your trip to some wonder of the world is leaving without you.

Courtesy of Casey Hekker, who is such an unbelievable trooper.

Remote Year isn’t an escape from your life. You will still meet assholes, disagree with family, deal with coworkers, fight with friends, get your heart broken. You’re just doing it with a better view.

Well that sounds stressful as fuck. Knowing everything you know now, would you do it again?

Abso-fucking-lutely yes. I would rewind this year and do it again in a heartbeat.

Those pics you see of laughter and parties are awesome and fun. But the times you’re struggling is when suddenly, you find yourself in a relationship with 70 new people.

You know that moment when your b/gf starts saying “we” instead of “I”? That’s going to be you. You’re going to start relating to the people who just pulled another all nighter of stress and work by your side and listen as their friends refer to your year as a vacation. Because even if they’re assholes, they’re YOUR assholes, and damned if someone other than you is going to make them feel like shit.

Aww that sounds sweet. So you DO recommend it then!

Well, no. That’s still hard because the truth is: you need to win the lottery. And I’m not referring to the price tag of Remote Year.

You’re excited you got in. You did the application, had the interview, dropped the deposit.

Jokes on you! Lottery just started.

You can’t have them.

You’re about to meet your two fearless leaders on this marathon of a year. Chances are, they will be awesome people who are going to do a good job, but whether or not they are going to be a GREAT fit for you personally is a total crap shoot. It’s easy to forget that it’s their first time doing this job, first time being in some of these places, and they usually don’t get as much support as they need.

That being said, they’ve been pouring over your applications and cyber stalking your social media with the tenacity of a dozen crazy exes. While you’re furiously buying out everything at REI and getting jabbed with vaccines, they are mentally preparing for the arrival of a group of people who are more or less their responsibility for a year. A YEAR. I can’t even keep a cactus alive for a month.

It’s just two people, that’s not too bad.

JK it’s not over yet.

You need to win the lottery twice.

Ever heard the phrase, “you don’t get to choose your family”?

Well congratulations! Here is your enormous new family. You have absolutely no say in who is part of it.

Personal growth and group dynamics play a huge part here. No two groups are the same. Some gel together, some don’t. Some people bail, and sometimes you meet your new boo on the first day. Sometimes you’re stuck with assholes, and sometimes you end up making a new best friend in the last month of the program.

All this and more play a huge part in your experience, so it gets hard to recommend that someone take a leap when you have no idea who’s on the other side.

Oh man, what if I get stuck with weirdos?

I wouldn’t know. My group won both lotteries. Sucks to be you.

We got the proverbial super fun parents who shower us with unconditional love and support no matter how much Dumb Shit we give them. And no matter how graceful they are at lying about how we aren’t that bad, rest assured that we shovel our fair share of Dumb Shit their way, and it is FAR outside their job description.

At 11 months in, they still approach any challenges, our Dumb Shit and all, with an enthusiasm and compassion that I can’t even comprehend. I would follow those onesies to the ends of the earth, and only partly because I can’t be relied on to locate anything other than food.

At some point I guarantee that you’re going to think you can make this trip happen on your own and do it cheaper and better than Remote Year can, and you are absolutely right.

So this travelling family is going to be a huge make-or-break for you. Because guess what? All those wonders of the world you’re about to see are going to look the same whether you show up alone or with a shitload of people. That just means you gotta win the lotteries so that the days, weeks, and months you spend on the way there are with people you really fall in love with.

The worst hike of my fucking life, with the very best people ❤

Follow along on Instagram for the times I suck at words.

Go Remote

Musings from the the global Remote Year community and…

Go Remote

Musings from the the global Remote Year community and beyond. Inspiration and resources for location-independent professionals.

Jess Chiu

Written by

Jess Chiu

Canadian freelancer, fried chicken aficionado, low key nerd. Currently in: Toronto, Ontario.

Go Remote

Musings from the the global Remote Year community and beyond. Inspiration and resources for location-independent professionals.