5 Questions To Ask Yourself Before Joining Remote Year

DISCLAIMER: The following post is based off of my personal experiences as a participant in the Remote Year program. These are my opinions, and my opinions only, based solely off of my personal experience and interpretation. You may feel differently, and that's okay. 


Since I began writing frequently, I've gotten a lot of correspondence from potential Remote Year participants who ask me for advice on whether or not the program is right for them. If you email me, the first thing I'll tell you is that nothing about this situation or this process is normal, and there’s no way to really know if it’s a right fit until you try it.

No one wants to hear that answer.

So, I've compiled a list of key questions you can ask yourself before committing to the program that could help you decide if it’s the right fit for you. I’d encourage you to ask yourself these questions and answer honestly, with the way you feel about yourself right now. This isn’t an exercise in addressing who you hope to turn into or how you hope to feel one day. Much like buying a pair of jeans, if you buy a size smaller in hopes that it’ll motivate you into fitting into them, both your ego and your wallet will be disappointed in three months. 

A video posted by Brooke Siem (@brookesiem) on

1. How financially flexible are you, practically and emotionally?

Remote Year is going to cost you more than you think. Full stop. No amount of budgeting can prepare you for the flexibility required to make the most out of this program. Practically, that’s an easy thing to wrap your head around, but emotionally, it’s a different story. For example, I know I can afford the entire year, but I also know that if I finish the year without any of my projects materializing or finding another source of steady income, I will have drained my savings. I also know that if I quit the program, I could extend my travels by six months to two years depending on where I went. One of those things is much more practical than the other.

Emotionally, though, it’s a different story. The last thing I want to do is go back to the United States without a job and without a plan, so the monthly credit card bill is a giant source of stress. I also don’t want to abandon my projects and take a full time gig just because it would give me some income. For me, that would inhibit the personal growth that comes from this experience (which is more valuable than money.) I’m extremely grateful to have this choice — I know most people don’t get to choose — but that doesn’t mean it doesn’t come with stress. On the whole, it’s very clear to me that people with the most stable jobs and least amount of financial worry are the ones who are most committed to the program.  

Hammocks are actually terrible to work in, but they are oh so good for the Insta. 

Hammocks are actually terrible to work in, but they are oh so good for the Insta. 

2. Can you truly work in any environment, and what do you need in your space to get your job done?

Working remotely, from a beach or a cafe or whatever else you see on Instagram, looks lovely, doesn’t it? There’s nothing like working on some spreadsheets with while you’re sipping a cocktail out of a coconut. Or maybe you prefer endless lattes with cute little cats of foam or a cotton candy cloud to gently sweeten your coffee. Maybe you even get the most work done from your bed, without pants. Co-working spaces seem cool too. I bet they’re full of interesting people. What a life. 

But what about the glare of the sun on the computer while you’re sipping that cocktail? You can’t input data unless you can see the computer. The cotton candy cloud is great, but the screaming babies in the cafe are not. Bed could be a great option for work, except the wifi might be pretty shitty (remember, RY only promises to outfit your rooms with a minimum internet capability of sending an email. Most of the time it's better than that, but you never know.) That leaves the co-working space, which is absolutely, 100% going to do everything RY promises. If the internet goes down, they drop everything to fix it.

For me, I can’t write in the co-working space or in a cafe. I need dead silence (to the point where I put on earplugs in my own apartment) in order to hear myself. I go to the workspace only to socialize or get mindless things done, like photo editing, invoicing, or taking video calls (apartment internet can’t always support those.) If you can throw on some headphones and focus for however many hours with your music du-jour, then the co-working aspect of RY is amazing. If, on the other hand, you need silence, a certain energy space, or specific creature comforts to get work done, then the co-working setup might not work for you. 

I swear, I tried to jump with everyone else, but like most group activites...sometimes it just doesn't go that well for me. 

I swear, I tried to jump with everyone else, but like most group activites...sometimes it just doesn't go that well for me. 

3. How well do you play with others, and more importantly, how easily are you influenced by others?

You know how Facebook is the worst because when something happens, inevitably one person says something buzzwordy and then the next thing you know, people who initially had no opinion on the topic start to chime in? Very quickly some poor person who named a silly dessert “Banana Sushi” (likely because you know, it looks like sushi even though OBVIOUSLY, it’s not) is being touted as ignorant and insensitive because he/she dared to slather some peanut butter on a banana, cut it crosswise, and use chopsticks to eat it. But since the banana dessert does not have anything to do with sushi, all of Japan needs to be outraged. Not only that, but all Asians everywhere should be outraged. 

Remote Year is like that. Ideas and emotions spread deeply and quickly. If you’re sensitive to other people’s energies or easily influenced by others people’s opinions, it’s so easy let things fester. Like Facebook, RY is an echo chamber. The more homogenous and in sync the group, the better the group fares...and vice/versa. 

This was particularly evident in Month 2, when Libertatem was in Koh Phangan, Thailand. The 70 or so of us were divided into three sets of accommodations, each about a 20 minute walk away from one another. About 30 were in a high end resort, 20 or so a mid range but still quirky and comfy resort on the beach, and the remaining 15 or so were in literal shacks directly on the beach. The issues with the beach shacks were endless and everyone had issues that ranged from infestations to rogue animals to cleanliness. Eventually, the problems were dealt with and in the end, everyone was moved out of those accommodations. 

My point in bringing this up is not to highlight the accolades or faults about RY and how they handled the problem. My point is to force you to ask yourself how you handle other people’s influences. 

I’m easily influenced by others’ energies and am constantly working on separating other's feelings from my own. I remember waking up after the first morning and joining two people on the beach. I wasn’t thrilled with the place, but figured I could deal with it (I also hadn't seen the other accommodations yet.) After talking to the two people and feeling their energy, I realized I should be a lot more outraged than I was…and so, I became more outraged. Then, every night, those of us in the beach shacks got together for a few beers. Inevitably, we would get to talking, and because we were separated from the other two groups who were living a cushy life in resorts, we didn’t have any balance. It was 15 people having a really shitty $2000 experience and talking about it, constantly. Once I moved out of the shack, my mind cleared because I wasn’t in that energy space all the time.

The consequences of this experience still linger. I'm skeptical of my living situation every single month even though we haven't had a repeat situation like we did in Thailand. A lot of people have left the program (between 15-20, it's surprisingly hard to tell) and initially, the majority were from that beach shack group. It’s not a coincidence. The larger community and the big picture had no chance against the echo chamber that happened on that beach. 

Even on my holiday vacation in Italy, I still needed to get away and spend a significant amount of time alone in nature in order to rest and recharge. 

Even on my holiday vacation in Italy, I still needed to get away and spend a significant amount of time alone in nature in order to rest and recharge. 

4. What happens when you can't control or change your own life?

Did you ever play The Sims as a kid? Remember how there are eight needs that you need to fulfill in your Sim's life — hunger, bladder, comfort, environment, social, hygiene, energy, fun —  otherwise he goes nuts and sets himself on fire while making toast or pees himself to death? Think of yourself as a Sim. Now, take the control out of all of those basic necessities. What happens?

What happens if you can't control your diet or get access to the food your body can handle? How do you feel if you have to share a bathroom, and your roommate leaves so much hair everywhere that it looks like someone shaved Robin William's back and sprinkled it all over the toilet? Are you okay with choosing between being surrounded by people all the time or going off alone, but missing out on crucial bonding experiences? Can you eat in restaurants where the meat sits at room temperature for hours and a baby literally lives in the kitchen? Do you have existing conditions that worsen with exhaustion and stress? 

Undoubtedly, you'll learn to live with a lot of these things. Or, you'll discover your limit. All travel, especially international travel that goes beyond "just like home but with a different accent," will always reveal issues that need to be worked on. This is also true with Remote Year, but the inherent nature of RY also means that you may not be able to change your situation unless you want to pay for it. If you show up to a hotel or an AirBnB and hate it, you leave and go find somewhere else. If your RY roommate turns out to be a drunken slob, or if you work the night shift but construction starts outside your window at 6am and goes until 9pm every day...well...that sucks for you. No one is going to stop you from going to a hotel, but you won't be getting reimbursed, either. 

Beers and meat wrapped in buttered dough is great until you're depressed because can't fit into your pants. 

Beers and meat wrapped in buttered dough is great until you're depressed because can't fit into your pants. 

5. How are those internal demons of yours?

Ok, so you're reading this and you're saying to yourself, "I know a lot of things are going to happen that I can't predict, but I'm pretty awesome at life and I can handle it." I'm sure that's true, but it's amazing what happens when all of your Sim requirements are messed with, and the next thing you know, you're in the depths of a familiar destructive pattern. 

If you're in recovery or struggling with addiction or destructive tendencies such as alcohol, drugs, eating disorders, or self harm, prepare for these issues will be tested on a regular basis. If you've experienced any sort of trauma, expect for life remind you that healing is not a linear process. If you struggle with any sort of mental health issues, know that they will likely show up even louder than ever before. You won't have your usual support system to cope, so you will have to figure out new ways to get through. It will be hard. It will be magnified. It might even happen in another language.

Of course, given that this experience will bring all of your issues up to the forefront and will leave you in a place where you don't have your trusted coping mechanisms and distractions, it's also going to allow you to heal these issues in an expedited manner. One week on Remote Year is like one month in the real world. If you're paying attention, you're going to quickly notice subtleties in yourself and figure out what works best for you. Just as soon as you figure it all out, you'll move locations and be tested on that topic all over again. Hopefully, you realize that something that threw you off kilter in Month 1 doesn't totally mess up Month 4. Or, you realize it's a non-negotiable in your life and that it's just a part of who you are. This realization is amazing. It's shit. But it's amazing. 

This photo (taken in Prague) pretty much summarizes the experience. It's just weirdness and question marks set in a beautiful place.  

This photo (taken in Prague) pretty much summarizes the experience. It's just weirdness and question marks set in a beautiful place.  

So, should you go? 

Based on these five questions, the ideal candidate for Remote Year is someone who is flexible, stable, and generally not all that concerned about the practical and emotional perks and consequences money. It's someone who's job is mindless enough to work anywhere, but challenging enough to keep them engaged. It's someone who in their worst moment, still wants to be around people. It's someone who is more comfortable peeing in a questionably wet bathroom than staying in a 5 star hotel. It's a person who has all of their emotional shit figured out, or never had any emotional baggage to begin with. 

That person sounds awesome. Also, that person does not exist. So, if I were you and I was considering this journey again, I'd aim to be comfortable with my answer to three out of the five questions. I'm not saying you have to have the perfect answer to each question, just to know yourself well enough to be able to predict how you will react, so when the situation arises, you're not like HOLY SHIT, WHERE DID ALL THESE FEELINGS COME FROM? ABORT! ABORT! ABORT! 

Would I do this program again? Probably not in its current iteration, but that's only because I know myself better, and I know myself better because I took a chance on the program in the first place. It's like asking me if I'd do Freshman year of college again. Yeah, I had some fun, but good God, it was painful. 

In a way, Remote Year has done exactly what it's supposed to do. It's made me uncomfortable, helped me become more secure in who I am and what I need, and forced me to deal with it. None of that would have happened without Remote Year because I never would have taken the leap to do this on my own. Now, this doesn't mean that I have to stick with it, because now I know I can do this on my own. Every month I decide if I want to kick the can down the road a little longer. You get that option, too.

So, if you're still overwhelmed with this decision and no amount of question and answers is helping you decide, just close your eyes and think about the the potential of the program. Does the thought of it make you feel expanded or constricted? If you feel free and open, don't think and just do it. If not, wait a few days and see if you feel the same way at a later date. 

As always, feel free to contact me if you have any more questions. If you have specific questions about packing or finances, check out my posts below:

5 Things I Wish I'd Been Told About Packing Before Traveling Around the World for a Year

5 Things I Wish I'd Been Told About Money Before Joining Remote Year