The Remote Show

Show Notes:

Chris's links:





Tyler Sellhorn (00:02):
Hello everyone. My name is Tyler Sellhorn, and welcome to another episode of The Remote Show, where we discuss everything to do with remote work, with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire. Today, we are blessed to be learning out loud with Chris Cerra. Since 2017, Chris has been living the remote work lifestyle from countless countries across four continents with his company, Remote Base. He is helping other people access this way of living. He is sharing ideal locations to work from remotely on his newsletter. So Chris, tell us, what problem are you trying to solve with Remote Base?
Chris Cerra (00:43):
Hey Tyler, thanks for having me on the show. I would probably start by saying that Remote Base is really simple. It's a newsletter. Everyone knows how email works and yeah, this thing lands right in your inbox. And what it really does is it helps people find accommodation at discounted rates that are available for the kind of medium term. So a month, two months, three months, the kind of length of stay that's perfect for when somebody wants to go and work remotely from a new location. Of course that's different from the kind of weekend breaks, and it's very different from a long term rental, or, like a 12 month agreement somewhere. Yeah. That's probably it in a nutshell. So discounted accommodation in a newsletter.
Tyler Sellhorn (01:28):
Okay. A couple items there that I feel like you're drawing out some of the really interesting parts about remote working and maybe working as the digital nomad, right. That idea that we've got out here that when we decouple our work from our location, there's a certain amount of freedom that comes associated in whether or not we're going to be able to achieve the lifestyle that you're suggesting is possible. Why do you think it is that remote workers are seeking that medium term length of stay in a particular place?
Chris Cerra (02:01):
It's a really interesting question. I think there's that horrible cliche, which is, you know, variety is the spice of life. And, there are other ways to look at how we kind of explore the world in a traditional sense, which is like 50 weeks in an office building, and if you are lucky, you get to experience two weeks of that on vacation. And actually when you work remotely, when you're not pinned to a location, you can almost just turn that on its head. You can spend about two weeks in your hometown with your family, maybe around the holidays. And then the other time is almost constantly available for quote unquote vacation destinations. So yeah, I think that's why that's, I, at least for me, it was something that I wanted having this lifestyle opportunity made me really question, why do we live in, in this place?
Chris Cerra (02:52):
Like what is there in my local vicinity that keeps me here? And then if you move around too often, it can become quite a stressful experience. I think it certainly started that way for me. I went through many locations in a short period of time and you kind of get caught in this living out of a backpack stress. That's the only thing I can really call it. So you just end up taking things a little bit more slowly and spending a little bit more time before, you know it you've spent two months in a place, but it's lovely because you get to really experience it and understand it. And like, I can go back to cities all over the world now and kind of walk around without even needing to look at a map. And I think that's wonderful. I think that's like just enough knowledge to have some familiarity, but still experience new things. And that makes me very fulfilled.
Tyler Sellhorn (03:39):
Okay. So I'm curious, what would 2021, Chris Cerra tell 2017, Chris Cerra about finding accommodations, working remotely? What are the things that you might hope to tell that I'm out into the world now, because I've got this opportunity to work remotely, right? I've left my office job and now I'm going to figure it out. What are the things that you might say to that person?
Chris Cerra (04:07):
I think one of the biggest pieces advice that I would give like past Chris is don't assume, like as humans, I think we are tuned genetically, like it is coded within us to look for patterns and to assume all kinds of things. Like we're just meaning making machines. That's what we do. And we'd like to try and find shortcuts for everything. And I think actually some of the more rich experiences that you can have are when you, you'll have to listen to your gut, of course, but try not to take things on an assumption level, try to really interpret them. I think that maybe that's a really abstract answer, but I think from the kind of travel and exploration side of that question, I think it needs to be abstract because there's just so many opportunities.
Tyler Sellhorn (04:54):
I'm wondering if you can tell us a story of 2017 Chris, like making an error in making assumptions that we can learn from.
Chris Cerra (05:04):
I can't think of anything that is like too specific, but there's maybe an example, which is like focused around the transition, 'cause that was really around the time that I was looking to transition from Chris who lives in London and works in London to Chris who doesn't really live anywhere, but works from everywhere. And I think one of the assumptions that I made was like, I need to have it figured out there needs to be a plan. And I think this happens actually a lot more and more, this happens like with the newsletter, I have people subscribe and they basically just want all of this information on accommodation. So they'll sign up and they email me back off the welcome email, and they're like, like I'm just getting started. Like I can't wait to have all these deals from you. Like help, basically, you know, it comes out in different words, but basically it's like, help me.
Chris Cerra (05:51):
Like what do I do next? And I think really the best advice or the best thing that you can do to counter any assumption, certainly that past Chris was making was don't assume that you're going to have it figured out, like there'll be countries where you don't realize that you don't have cellular until you get there, and that's okay. I think there's something that's missed about this lifestyle is the way it helps you build resilience. And I think that's something that has built in me over this past four years, like the ability to just kind of handle uncertainty and know that there isn't this kind of like long plan there isn't like a 10 year plan with everything figured out, at least not for me and not yet. If you do have that, I think that's fantastic, but if not, you know, roll with it. And when you do get there, know that you have the skills to just figure out, okay, like I need to get some cell signal. I need to get a SIM card or whatever it is, whatever the problem might be.
Tyler Sellhorn (06:43):
Shout out to developing resilience and being able to handle uncertainty, even just as a remote worker period.
Chris Cerra (06:49):
Of course. Yeah.
Tyler Sellhorn (06:50):
Let alone one that's choosing to travel as they do that. Okay, so let's go back to that question that people have been asking you in their first receipt of your newsletter. They're asking the question, well help, what do I do next? Tell us Chris, what do we do next? If we want to be able to find a good places to work from?
Chris Cerra (07:11):
Yeah, I think it depends kind of where you are in what I'll call your "about work journey". And there are other ways to cut this up as well, like pre-pandemic, during, and post.
Tyler Sellhorn (07:22):
In fact, that's my favorite question right now. So maybe that's the one that we ought to ask is tell us what you think about remote working and especially remote working abroad in that pre-pandemic, 2019 and before versus what's happening right now versus what might be in 2022 and beyond.
Chris Cerra (07:40):
Yeah, so for accommodation, which is, I guess, where a lot of my thinking happens around this for accommodation, it's actually a lot more difficult post pandemic or it's becoming more difficult post pandemic because so many more people now have figured out, oh, if I'm going to work from my kitchen table, I can do that at the beach or I can do that in Paris. And so the market's kind of flooded from a supply side with that in mind, it just makes it harder to find deals. A lot of my time is spent basically in Airbnb or on other platforms trying to figure out where the kind of deals are, whether or not something's really suitable for the audience. But I think, and this goes of the preemptive side of this question, which is like, if you are looking for help and trying to get into this, how do you figure out what you need?
Chris Cerra (08:26):
There are so many accommodations open to you as somebody who can work remotely. And it largely depends on like what you do. For example, Tyler, like you are running a podcast, you need to record stuff. You can't do that from a hostile or from a loud, busy coworking place. You need what I call private accommodation, whether or not that's an Airbnb or a hotel. That's what you need. If you are a writer, you know, you're good, you just need a laptop and you can kind of stay in a hostile if you want and just travel that way. Part of it is geared by profession and what it is that you need to do in order to earn, and another part of it is of course driven by what your personal preferences are and, do you value your privacy really badly? Maybe you are like a really, really social person and you just want to be around people.
Chris Cerra (09:13):
Maybe that's something that's things through the pandemic as well, but these are the considerations, and so when people come and talk about help or ask for help and like, what do we do next? Really, I try to understand where they are and like where we are, they on that matrix of like personal needs and professional needs versus accommodation needs and figure that out. Some people don't even have a job, yeah. They're just like, oh, like I know I want to do this and I know that those jobs available, so I'm going to take a chance.
Tyler Sellhorn (09:41):
Okay, tell us the story about you just for yourself. When you think about balancing personal needs and professional needs, what is on your personal matrix for deciding where you are going to base out of?
Chris Cerra (09:54):
I travel with my partner and pretty much exclusively stay in Airbnbs and that's really down to partly our work, but partly, yeah, partly it's down to the personal preference. And there's also like a practicality question that comes in like, okay, if you stay in a hostile, it's a really sociable environment. It's a great way to meet people, but we are going to be there for two months, and most of the people that are there, they're probably going to be in and out maybe every few days, maybe if we're lucky every two weeks at like tops. So it becomes a level like a question of practicality around, is it practical for us to kind of integrate into that location with people and also even more, on a personal side, if you're in a hostile, you might rely on a cleaner that comes maybe infrequently, you don't know what the schedule is, that kind of thing.
Chris Cerra (10:51):
An Airbnb is like as close as you can get to a home of your own. And so I like to say that I live in Airbnbs. They always kind of feel a little bit like home and you can pick, you can find stuff that you think, oh, like this would be a comfortable place to be for an extended period of time, and it has like a desk maybe, you know, there's enough space for both me and my partner to work, so that's what really drives us in our choice. Maybe even having a partner is another factor on that, right? Like I have people on the newsletter who have kids and it's like, "I only want two bedroom places." And of course that that's a, a practical requirement for you, so there are many things to consider.
Tyler Sellhorn (11:33):
Yeah. Obviously it depends on who you are and who you're traveling with. If you are going to choose to travel while working, one of the things that I was interested to think about as you were describing kind of the checklist that you're using there, what are the hints when you are surfing the web, right? Looking for potential accommodation, what are the things that your trained eye might see that a novice would not?
Chris Cerra (12:00):
Yeah, good question. So I think the best way to address that is for me to talk a little bit about how it kind of started because really the newsletter grew out of an Airbnb wishlist. So in Airbnb, you know, you can just favorite accommodation, and create a wishlist. And I was doing that with my girlfriend for maybe five years ago, with the intention of moving this way. And yeah, from there, it got to the point where there were just so many on the list and things like availability started to become a bit of a problem. And of course the more that you see, the more of an opinion you have on the whole data set. So through looking at them and seeing so many, we pick up on things like maybe a host will move furniture around to make a place look bigger or possibly deceive you.
Chris Cerra (12:50):
I don't want to say anything negative, but that can and happen. There's also obviously reviews and I mean, there's other stuff, right? So we do some other stuff, which is we check other data around how many listings there even are in that place period, to see like, is this a deal or is it not a deal? Airbnb kind of shows you if there's more than 300 are results that fit the criteria, they kind of cap you, like we have more than 300, here's like 12 and then hit the next page when you want to go to the next and see more, but there are other ways to get to that data. So we do a little bit of that and we do a bit more of a deep dive on like, is this really a deal based on what everything that is available, but yeah, on a more kind of granular level we're also looking at has that host put five chairs around a four person table, because that's not cool. So yeah. There's definitely stuff that crops up.
Tyler Sellhorn (13:44):
That's interesting to hear you talk about the filters that you use as you're clamoring around in these marketplaces, right? You know, sometimes they can be cluttered, right? And how do you decide this one's legit or this one's not legit. Some of those cross filtering, obviously pagination is going to be a thing when we look at listings. And so making good decisions about what we're going to do, and that goes back to the things that you were talking about earlier of like, what are your personal needs? What are your professional needs? What are you going to filter on to look at the accomodation that your needs? Okay.
Tyler Sellhorn (14:17):
A thought that you said earlier, that was really interesting to me was the idea that, okay, I'm going to flip it around, right, instead of spending 50 weeks a year in one place, and then traveling wherever I please the other two weeks of the year, maybe on vacation, and, and sometimes that is always come home to visit. Let's flip that around. Let's say, okay, I'm going to go explore, and then I'm going to come home to one location for those same two weeks that I might have taken off from work.
Tyler Sellhorn (14:46):
That's rhyming with Matt Mullenweg, that's kind of his phrase when he thinks about people joining automatic and it's constellation of companies is to say, we want to flip it around, right? We're going to say four weeks of the year, we'd like to tell you where to be and then the rest of the year you work wherever you like. And I think that that idea of exploration, you said that word right off the top, was to say, "Hey, let's be explorers. Let's live the lifestyle of exploration." What do you think it is that drives us to even desire that sort of way of living?
Chris Cerra (15:21):
Oh yeah, that's a really big question. I think it'll probably be different for different people. There's obviously something in us as a species. Right, which is like, we need to know where our boundaries are or push the boundaries, maybe it's a territorial thing. I'm really not sure. I can't speak for the species, but for me personally, I think it's, I have like family history, which is outside of the country that I was born in and I'm from, and so I think part of me always, certainly maybe earlier on, in my explorer a career or in my explorations, I think yeah, that was driven by like going to places where I know my heritage is and trying to experience that. My grandfather would be farming land in the south of Italy, and like, that was how he lived. And so I just think it's absolutely alien and amazing that in the space of two generations, like I can take a laptop and a wifi connection with me around the world and make a living that way, it's astonishing. It absolutely baffles me. I think it's incredible.
Tyler Sellhorn (16:28):
You have worked on the very same land that your grandfather did.
Chris Cerra (16:34):
I haven't, but that would be really cool actually.
Tyler Sellhorn (16:37):
We could imagine that very scenario occurring.
Chris Cerra (16:40):
Yeah. Yeah. I think that would be, that would be a push, but yeah, like that kind of thing, right, to just be able to go back there, and here's the thing it's not so much that I want to take my laptop and work on that land, but it's that when the day finishes and the laptop lid goes down, there's no reason that I can't be there and, see that sunset and breathe that air and feel all of the things that they felt like that's really what it's about. It's not really so much about the work aspect, it's more about the human experience. It opens you up to that.
Chris Cerra (17:12):
So I think it's a really powerful thing, and I think it can be really fulfilling. And I think that people have a barrier to that, they imagine that there's lots of societal constraints that will limit them from doing that. "I need to buy a house. I need to get married. I need a $80,000 car," and you don't necessarily need those things. You can have them if you want them. If you're very fortunate, you can have both. You can have that sat in a garage for, you know, nine months of the year and travel the world simultaneously. The question really was about exploration, wasn't it? And I feel like we've gone a little bit off topic.
Tyler Sellhorn (17:44):
We explored far afield into a really, really great space because you said it better than I did. Right. You said I'm there to experience the life that he lived, not necessarily working on the land that your ancestors maybe did. And I think that's an amazing fun idea to like say, yeah, I'd like to look at that same sunset. That's a really cool idea. Just a side note, I have a colleague at my day job where they are living in the land of their ancestors. They are a New Yorker, shout out Charles to you living in Brittany, but you know, once upon a time had grown up in New York, but has moved with his family to northwestern France and you know, lives where Botania, if there's a reason why all of those words are very similar is because tho those are the places that his family is from originally.
Tyler Sellhorn (18:36):
So, okay. One of the things that I want to invite you to kind of help us conclude with is to think about why is it that we choose to locate someplace in the first place? You mentioned the idea of like I'm going to travel, where my ancestry is from, what are some other motivations that you've heard of people traveling? What are the things that are drawing them away from their hometown or drawing them back to their hometown? Or what are the different things that you've seen push or pull people around the world as they're working remotely?
Chris Cerra (19:13):
Yeah. That's another good question, Tyler. I think perhaps some of this is, is sat in this idea that the grass is always greener and for so long, we could never do this. And so that was really what people wanted. You can think into the history on that for a long time, right? Like the industrial revolution factories needing to punch in and out of a factory, like you need to be live in a commutable distance in order to get that job. And over time, that's just the way that, the way that things progressed. Now, the information revolution, if you want to call it that the rise of the knowledge worker, that means that we kind of had the tools, the real tools, internet, technology to do that, but we weren't able to flip the switch like culturally and draw ourselves away from an office.
Chris Cerra (19:59):
And also there's lots of learned behaviors that are perfect for in-person collaboration that aren't so perfect for remote working. But I think that that has a strong basis and desire, like I think that's why a lot of people want to go away, it's because it seemed like this thing that you couldn't do. In terms of where to go, other reasons to go to particular places, I'm not a really big fan, I'm actually originally I'm from Manchester in the UK and a fun fact about Manchester for all of the listeners, and it won't be the football thing because everybody associates Manchester with football, but it actually rains here for more days in the year than it doesn't rain. And so for me, I'm not really a big fan of the rain Tyler. That's no surprise. And yeah, so for me, it's like, I want to go to where it isn't raining please, that's where I'll go.
Chris Cerra (20:53):
And yeah, so I think things like climate, things like if you can earn in a strong currency and spend in a relatively weak currency, then you're going to come out on top. Maybe that's how you have your $8,000 car. But yeah, that's the reason I think there are some, probably some side notes here, which are like, I love a good cliche. So along with the varieties, the spice of live cliche, we'll add the other one, which is the one about travel, not really fixing anything. If you are not really happy because of various things, wherever you are, don't expect travel to fix that, find the core values and all the rest of it that make you happy, where you are and then take those on the road and you'll have such a better time. But yeah, I think maybe that's another driving factor. People are seeking happiness and they think that that's something that they can find in another place.
Tyler Sellhorn (21:43):
Outstanding, and you know, you mentioned weather, you mentioned priorities. I am not a digital nomad. I am a dad in the Midwestern United States. Right, but those are the things that were important to me.
Chris Cerra (21:56):
Tyler Sellhorn (21:57):
Was to be able to raise my family in a place that had lots of resources for families. We live near family here. My family moved to here to be near my family and my wife's family. And so I just really appreciate your invitation to say to ourselves, what is it that you want out of life? Is the grass greener on the other side?
Chris Cerra (22:20):
Tyler Sellhorn (22:21):
It may not be, but you need to think about what would fulfill you in your life as you are seeking to figure out what it is that you're going to do and where you're going to do it from.
Chris Cerra (22:33):
Yeah. Entirely. It's a really big decision, right? Like it's a whole lifestyle change. I've heard it on the show before it's recently, actually. But the term slow-mad, like when we talk about digital nomads, everyone does air quotes. I don't know, in some circles it has like this connotation, certain connotations, I should say. And yeah, even as somebody who lives the remote work and travel lifestyle, I find myself kind of, I'll read some stuff and I'll be like, oh, like that's so assumptive or lots of stereotypes have been referenced and stuff like that. And I think if you are considering that lifestyle, do won't get caught up on that, make the decision to pursue what's valuable to you and understand that. And this is maybe a separate point, but lifestyle choices aren't forever. Like you can do this for a set period of time or a period of time and then change your mind and learn.
Chris Cerra (23:28):
Actually I really want to do this and you might go back to your hometown, but you also might settle somewhere where it's warmer and cheaper or whatever else, where they have nicer vegetables that you can't get at home or something like that, you know? Think about it as a way to access more information about yourself. So you kind of have to set what it is in your mind that brings you joy and makes you happy and allows you to be fulfilled. And then you put yourself on a pathway. Maybe you uncover more of that and more and more and more, and it's certainly the best decision I ever made.
Tyler Sellhorn (24:05):
Well, let's conclude right there to, you know, be drawn into becoming more considered, right? less assumptive, right? And more purposeful about the ways we go about the world. You know, as we slow-mad, nomad, there's no madding at all in my life. I'm rooted to the spot as it were, but I hope that we all come into this with this idea that we can be very purposeful in the ways that we are choosing to live our lives. Thanks to decoupling work from location. So thank you for that reminder, Chris, we appreciate you.
Chris Cerra (24:42):
Thanks for having me, Tyler. It's great to chat.
Tyler Sellhorn (24:46):
Thanks so much again for listening to the show and be sure to check out WeWorkremotely.com for the latest remote jobs. And if you're looking to hire a remote worker, We Work Remotely is the fastest and easiest way to do so. As always, if you have someone we should talk to, any advice you have, or if you'd like to advertise on the podcast, please reach out to us at [email protected]. That's [email protected]. Thanks so much for listening, and we'll talk to you next time. 

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