Unpacking the remote work movement with Jordan Carroll

Unpacking the remote work movement with Jordan Carroll

Full Transcript

Curtis Duggan: Hey everybody. Welcome back to Remotely Serious. This episode is with Jordan Carroll. He is the remote job coach, and we had a great time catching up in person, actually in Lisbon at the running remote conference, and a few, I guess a few weeks later, a few months later, I don't know how long it's been, I guess it's been a couple months now.

We decided to catch up and jump on a pod together. So I'm really excited about what we talk about and Jordan has so much experience as an influencer, as a creator, and as a remote job coach in the remote workspace. So I think you'll be excited to hear about what he has to say. Let's jump in.

Hey everybody. Welcome back to this episode of Remotely Serious. I'm here with Jordan Carroll, a k a, the remote job coach. I was just watching a video that you put out. I think it's fairly recent. It must be pretty recent because it has footage from the running remote conference in Lisbon. But it was asking CEOs if remote work is dead.

And so we're chatting in this kind of counter-revolution backlash. Late spring, early summer of 2023 when the headlines are saying remote work. It might be over, it might be backsliding and you by looking at your bio. We met in a little bit for the first time a few months ago, but I've had now had a chance to go back and look at your bio and we'll get into that.

But one of the things that stuck out was like, you've been doing this a long time. It said something like, I. Since 2013. And in the last 10 years, I'm sure you've seen cycles of it, including the huge cycle we had in 2020 and 2021 with the pandemic. So what do you think when you produced that video, which had awesome music, by the way, what was your conclusion about whether there's a backlash or a retrenchment of remote work?


Jordan Carroll: Thanks Curtis. Appreciate it. A lot of stuff to unpack there. I think. The interesting part about that video first of all,

Curtis Duggan: running remote was fun. Give people the con, the context. It was fun context that we went to Lisbon, we had a, an awesome time, sunny day and yeah, it was the year before.

It was in my home country of Montreal. I'm not from Quebec or Montreal. I. But it was closer to home then, and it was a little bit more subdued. Still a great conference, but it was do we need to wear masks? Oh, we're on. We're all seeing each other for the first time. Yeah. But this year, so that was 2022 this year in 2023.

It was a big sunny day in Lisbon. A lot of fun and we'll get into maybe some of that and they're gonna do it again there next year. So yes, running remote enterprise. Focused remote work conference in Lisbon. Lots of digital nomads and remote workers show up, but it's a combination of different things, but mix.

It's a mix. I was really, and you were a moderator, right? I was an M mc, yeah. Yeah. Mc of the mc. Second stage. Mc, sorry. Yeah. It's clo, yeah.

Jordan Carroll: Close. Yeah. Basically, Host, massive of ceremonies, if you

Curtis Duggan: will. Yeah. On the cool stage. The cool stage where the it was the hot stage

Jordan Carroll: alternative.

It was hot man. Yeah. Like they have ac on the first day, the second day sun beaming on. But yeah, it was a cool stage cool factor to, to your question. Okay. Cycles. It's interesting because in the 10 years or so I've been working remotely. I've never seen anything like what happened during the pandemic.

No one has there's never been a leap like that of adoption for remote work. But what people get wrong is that they try to compare what happened during the pandemic, like remote work during that to remote work before. And it doesn't really compare because it's not the same like in the big piece that I got from the whole conference as well as from those interviews that I did in that video was that.

Remote work is not about where, but that's what everybody focuses on. It's like where work gets done, is it in the office? Can I work from anywhere? Can I work from this state, from this city, this time zone, blah, blah, blah, blah, blah, blah, blah, blah. Remote work is about how it's just a different operating system.

It's a different way of thinking, and most companies are not thinking, especially the ones that were forced to be remote, are not thinking about how to change work. They just scrambled. To get everybody on a Zoom call enough times a week to feel important. So of course, remote work didn't work for them.

They didn't change how they worked. They tried to replicate the office virtually, and it just doesn't really work like that. And I've worked for companies that are awful with remote work, like during those 10 years I've worked with companies that are awful with remote work and have no standardization, have no policy, have no thought, no intention.

And then I've worked w. For a couple companies who are really awesome at it. And so it's like I've seen both sides. And I understand both sides. And I also understand this knee-jerk reaction to go back. But here's also what people are forgetting is that there is a phase of time in which we need, and the world needs to adapt.

And what happened was like the pendulum swung really far in the remote work way because it had to. But of course it's gonna swing back when it doesn't have to anymore. But it didn't actually didn't swing back as far as you might think. Yeah. Like we're still working way more remotely than we ever have in history.


Curtis Duggan: We've moved the goalpost or the Overton window as they sometimes call. Yeah. It may seem like it's backsliding, but it's still, we forget history and realize stabilizing is

Jordan Carroll: a better word. Yeah. It's stabilizing, stabilized at a new place that's still going up. That's the thing is like it's stabilized with an upward trajectory.

It's not stabilizing with a downward trajectory. And that was what I got from the conversations that I have about, 'cause it just makes sense. Like the way that remote work is going to be done in the future and the way that companies can have a competitive advantage. Whether it's hiring, whether it's cost, whether it's whatever.

Like of course. Yeah. All these big companies that have these massive leases, On real estate are gonna be like, yeah, let's go back to the office. It's yeah, you gotta justify that spending. So it's yeah.

Curtis Duggan: Yeah. I I get it. I don't view a lot of media through the news, through the lens of conspiratorial theories or conspiracy theories, but I do start to think all of a sudden, when the.

Not to get too nerdy or wonky, but when the interest rate and the eco, the economic situation around the lending against commercial real estate suddenly becomes unraveled. And, Silicon Valley Bank almost imploded, or it did implode. It was totally bankrupt. Yeah. And then bought again, and that unraveled a few other banks.

Then eventually you realize that downtowns are struggling to attract office workers that they have relied on in the past, and therefore, commercial real estate buildings, which are often sometimes owned outright, but are often heavily indebted Yeah. Suddenly are worth so much less than whatever the asset value was.

When the loan for the commercial real estate was started. Again, not trying to be too wonky to, T L D R office buildings aren't worth as much, and that's really, that's billions of dollars of pain. And then, oh, suddenly there's a bunch of media articles. We really should get back to the office.

Or it's time to admit that remote work. And it's oh, okay. Ah, I wonder if in some, Soho Club or country club in Connecticut or Harvard or New York or San Francisco, Marin County, where the halls of power and people are discussing things. Someone in commercial real estate and someone in banking is talking to someone in media, like a, like an episode of succession and saying, push this narrative that we need to get back to the office.

These office buildings are gonna tank the banks. So I've been. I've been opening my mind to. Yeah. I don't even think it's

Jordan Carroll: really a huge secret that kind of thing is happening. You had Sam Zell, who also passed away recently, but he, yeah. Went on record saying that remote work is bullshit.

Of course, he owns what the most real estate. In the world, or at least in the us. So it's yeah, of course these people are gonna have certain narratives that they're pushing into the media. And then of course, if you think about the, how money works and how lobbyists works and how all these things work, it's like people are gonna have special interests and they're gonna pay the PE they're gonna pay to have that type of influence.

And media is a great way to do that. And people see headlines nowadays, like they just believe it at face value. So you can really change the culture just by pushing headlines in a variety of different media outlets. One

Curtis Duggan: of the things I've been thinking about on this kind of topic of where it will go is that, I find that companies, they can appear to be these large institutions that are guided by invisible hands and unseen forces.

But in reality, a lot of firms, or most firms, I would say almost all firms are truly a. Reflection and a personality of the c e o. What sometimes it's a founder, c e o, often in larger companies. Yeah. It's just a regular c e o. And so when I look at remote work and what you know, what to think about it, I find it sometimes on a spectrum in terms of not remote work itself, but just whether it's right for companies to succeed.

And so you'll have Sam Cell, r i p, and others, and even Paul Graham and some others, and Certains. Silicon Valley founders now are saying remote work is a mistake. We need to go back to the office. They're pro office. And then you get on the other side of the spectrum of US spectrum influencers. For example Steph Smith, who's now with a 16 Z but has long been a writer about remote work and async work is anti the office.

She's saying, if you believe the office is better than remote work, you're wrong. Remote work is superior and I would like to think there is an opinion, or there is a position rather where it's just a choice now. It's a marketplace. Yeah. And a C E O can. Just decide Hey, we are in person in downtown San Francisco.

We're in person in Silicon Valley, or some any city around the world. And then someone else can say, we're a fully distributed async company. I wonder whether there can there just be a choice? Are the CEOs who maybe some companies should be in person, some should be remote and we don't even have to do.

Have a debate. It's just, to me it's the power of choice. But I'm just curious how you think about that. Do you think, yeah. Do you think CEOs who want everybody back to the office are wrong, or are they just exercising the right to choose and people will sort themselves where they feel that they're treated best?

Jordan Carroll: Yeah. I think again it goes back to instead of the, where it's the how, it's starting with the how what are these companies? Wanting to create and how is it that they're gonna create these things? And when you start from the top, it's like how do they structure their organizations from a communication perspective?

Like what do they value? And of course, if they value face-to-face interaction, they value all those things. Yeah. Maybe they'll get some people on board for that. I think as time goes on, there's gonna be more and more options for people to work more flexibly. I think that the choice. The choice part is the most ideal for job seekers and for people that are working there, but it's rarely the most ideal for the employer.

It's actually a lot more beneficial for an employer to take a pretty good stand on that. If they want people in the office or if they wanna do, full remote, because the hybrid trap is like really difficult for companies because then you're trying to manage two different. Styles of working, where that also can potentially bring up animosity between different workers who have more choice than others or who are, remote three days a week, but they wanna be remote more days a week than this person has some sort of childcare things.

Then they get an extra day. So like you are just like having to make a lot of decisions around things that if they were just pre-decided you wouldn't have that issue. So I think a lot of the companies that are going somewhere in that middle are having. An even harder time than either of the polls.

Yeah. What I like is fully remote, but let me get you a stipend for a coworking space or, yeah. The have the ability to give them, give employees an ability to go work somewhere where they feel like they have interaction with people. But again, I think, and that's different like this, all this stuff is like different based on choice.

I personally don't think that. Work needs to be social in the sense that my social life is dictated based on my work life. Like I need to go into an office to get my social needs met. I don't think that's a good way to look at your social life. I think your social life should be the things, the hobbies, the interests that you do, things that are outside of maybe making money or outside of.

What you do on a daily basis for work is like you're seeking out those social

Curtis Duggan: interactions. So yeah, that idea of the office's social life really does seem like a 20th century idea that was comprehensively satirized by the office shows and by all kinds of media from 10 or 15 or 20 years ago. And it does seem like a relic of the past now that, you.

The happenstance of where you happen to commute to is that suddenly becomes, 30 or 40 years of your adult social life for some people. Yeah. Yeah. Just, but anyway, in that video you were interviewing a lot of great people, thought leaders and others. Gonzalo Hall, chase, Warrington, Tara, Ani, nacho.

In talking to everyone at Lisbon, I'm sure more than just for that video, over the course of several days, you probably had many conversations. Did anything surprise you? Did anything seem new or different about 2023 and what was being discussed that you hadn't seen in the prior nine or 10 years of covering and participating in this space?

Yeah, I

Jordan Carroll: think Ryan's. I think a lot of people Did you go to Ryan's talk? Yeah, the first one, yeah. I think his talk was fantastic and his insights during my interview with him were fantastic. And I just loved how he brought in the Gartner hype cycle, which is similar to the innovation curve, which really gave us perspective with where we're at.

And basically what he said was like, we're in chaos, but that's exactly where we should be right now. We're in chaos because. We've hit this trough of disillusionment. We've basically had the part that we're in this innovation curve or in this hype cycle is a low one to where people are restabilizing and resetting their expectations around what this means.

And out of this comes a lot of people and a lot of companies who are gonna be working on the next generation of solutions that really bring this to the forefront. That to me, just, I knew that kind of stuff, but the way that he explained it, I just thought was like way more clear than I'd ever heard it be explained.

And then the way that he talked about AI being in, you know, incorporated in that and just because of the level in which AI has been, I. Developing in the past, four to six months. That stuff was all new to me. I was like, wow. This is gonna be insane to see how AI plugs into all these remote work tools and teams and how we're gonna interact with each other.

And I. Yeah, that like I really liked also that he had a lot of memes, so

Curtis Duggan: that was cool. Yeah. Yeah. And then now Apple has also put out a high-end vision of how we might interact with our work our work surfaces, our workspace in three dimensions and holograms that are sitting. Resting in front of us through a advisor or through a Vision Pro device.

So the, whether everyone gets an Apple Pro for three or four grand in the next two or three years, probably not. You don't want to get that stolen at a coworking space or coffee shop. No.

Jordan Carroll: Or you just are like in your world and people are stealing

Curtis Duggan: all your other shit. Yeah. Yeah. But I think it's.

Painting a picture of maybe five to 10 years. So ai, right now it happens, every month goes by the three D or spatial computing thing I think will take longer, but eventually, we'll, maybe not have to lug a second monitor around. Not that everyone does that, but we'll maybe have a, have an easier time.

So there's definitely a technological trend that's coming in the next decade. Over, over what period were you writing your book Remote for Life? During what time were you drafting that book? When did you release that? Yeah,

Jordan Carroll: that was November 22nd. Also, just real quick about the headset thing, I always get sick.

I always get sick with those I feel like I wanna throw up. So I can't imagine that being something I'm like in. For a full day of work, I'd just, I'd have just vomit all over me.

Curtis Duggan: I don't know if you, I remember I, I tried the f like I got the first Oculus in 2013 or 14 in a Kickstarter. I've since sold it off or something, but for a couple years I was into it.

I I don't have a meta quest or whatever. I think I tried an H T C valve just to get nerdy a little bit about the product names. But same thing. I think I wasn't someone who got sick immediately, but it felt 90 minutes was the absolute maximum. And that's not gonna support anyone having a normal workday.

Yeah. Or doing anything for, you can't even watch a movie if you get sick at the hour mark. And a lot of people, it's five minutes in, they can't, so yeah, it was like 20

Jordan Carroll: and then I was like,

Curtis Duggan: yeah, I'm gonna, I'm gonna puke. Yeah, I like that. You think based on Apple's brand associations and the track record that they've created, that they would have eliminated that for everyone, regardless of, size, shape, vision, impairment all the different ways that people's vision is effective and their, the way the different people's brains work.

But who knows? It might be that not everyone can use this properly or it's disconcerting. So yeah, AI is much more obviously, Taking off quickly. And its applications are so much easier. You can go, oh, gimme this code, or write me up this copy. And it does it, and it does it pretty well and there's 10,000 other things it can do.

But yeah, I was just thinking about when you write a book remote for life and then things change, like AI comes along, things happen really quickly. Do you think about. Updating it a version every year or making sure that the, the chapter, it goes to chapter 20 and then chapter 21, I'll add a chapter about the latest AI and that kind of thing, or is it timeless, yeah, I

Jordan Carroll: mean, going into writing a book, which I started that the first draft of that outline was like 2018 or 19. Was the first draft of the initial outline and Me thinking about writing a book seriously, and then I put it down and I was just like, nah, it's not the right time. And I'm really glad that I did that because if I had written it then, and then the pandemic happened, I mean that really changes the trajectory of the book to the point where it wouldn't even make sense.

So I'm actually glad that I waited and then I ended up restarting the process in January of 21. We ended up publishing in November of 22. Now to the question of will I update it, I have a book resources link that comes with the book when you open the book. Right away it says, Hey, here's where you can find all the resources for the book.

That's what I intended on updating was like this bank of resources rather than amending the book and reopening it and redoing that. Although, who knows? Yeah, maybe someday I'll do that. But at this point, what I tried to do with the book was create enough evergreen content in there that someone could read it and be like, wow, okay.

Like 10 years from now there's still stuff in there that's. Helping people and extremely


Curtis Duggan: Yeah. I think there's some principles about location independence, regardless of whether it's on a laptop or through a visor in a three D Metaverse, or in Bulgaria or in Croatia, or in.

Columbia, that'll just be principles that are true in 10 years from now and 20 years from now. Yeah. About how to do good work while you're LOC location independent. But you're, you are the remote job coach. And I think that I've been, I. Remote by default. I would say probably for seven or eight years.

And it's I don't wanna say it's a similar thing to you 'cause I probably had a different trajectory, but you do call out on your site that you've been a remote employee and a remote entrepreneur and a remote freelancer. It's breaks down that there's not just one way to be remote and you give the journey of that.

When people are specifically looking for a remote job that's different than some of the stereotypes that are put out there about. Digital nomadism and remote work, which is that, there is a version of this where people say Quit your cubicle and become an entrepreneur. Start Amazon.

Drop shipping. Start. Yeah. Startup. Start a blog, start some kind of be a YouTuber, very various way, be, become a business person. Find a way to make money online as a business person. And you've got job right in the title. How has that branding affected what you're doing? Are you are you specifically helping people take the job they already have?

And have the hard conversation, do the negotiation to make it go remote? Or is it really more, and it seems from what I've seen for some of, when you're posting remote jobs that are out there, it's also mostly about helping people go find a remote job. But I'm curious if that changes when it was hot.

Remote market, 20 20, 20 21. Bull Market Tech jobs everywhere. Now 2023, it's more like layoffs. Ooh. Maybe the employers think they have the leverage again. Have you seen that shift a bit in the last couple years in terms of your core branding and the kind of people you talk to and coach?


Jordan Carroll: Yeah, it's a great observation. I think for me, I wanted to be very clear initially when I was first creating this brand, which was 2019, that I didn't I didn't want. People to think that I was helping them become an entrepreneur. So there's a whole class of people that don't have any interest in becoming an entrepreneur.

Maybe they're interested in freelancing and having a few different contracts, which is a form of self-employment. But these aren't people who wanted to start a drop shipping business or start some sort of product base. It's like they want to do project work for companies. So I wanted to cover a spectrum of people that didn't really relate to the entrepreneurship.

Like maybe they have. Entrepreneurship tendencies. Maybe they have thoughts of like eventually becoming an entrepreneur, but they know that right now the way in which that they can access remote locational independence is through an employer that's gonna pay them consistently to work a job that's actually remote and flexible because there are companies out there that do this.

I've worked for them, I have friends that have worked for them, and it is a smaller subset of companies that do this and truly let people work from anywhere, but. That's exactly the reason why my job exists is because people don't know exactly how to, one, build a strategy for figuring out where these companies are, which ones are the ones that are actually remote, which ones are the ones that are actually work from anywhere.

Two, how can they brand themselves and articulate themselves in a way that these companies understand that they have the skills to do it, what it is that they're asking someone to do. And then three, network. Like how do you connect with people at these organizations to increase your chances of getting referral rather than just applying online in the abyss?

So for me, I've seen many different cycles in, in the job marketplace where in 2019, there really wasn't. Huge remote work. Even be, before that as well. But like in 2019 compared to 20 20, 20 21, it's like remote was still bit a bit obscure and like people didn't really, didn't understand what these companies.

And then 20 20, 20 21, like there's the word remote being used more, but companies aren't really sure what they're doing. And now on the outside of this, it's again, we're hitting that again, that cycle in the marketplace where yeah, there's a ton of layoffs. Funding's tough, like money's tight for people.

It's a hard market, so you really need to understand how it is that you can stand out right in that type of market because you're going up a lot of against a lot of different competition and the types of companies that are really, truly hiring fully, remotely. Like they have a ton of leverage to pick from the best of the best.

So you gotta be able to not only. Be super competent, but then also build the relationships and then articulate your value all at the same time to be hired. And that's truly what I help them with, is like building the strategy to, to do that, to show up as a package that's a good fit for these companies.

Now I've also, I. Ultimately help people do freelancing as well. It's not something that I advertise as, like I have actually have friends that are like the freelance Co. I have a friend named the Freelance coach and we'll collaborate on certain things or we'll talk about certain things that are happening and I'll help people, find contract work too.

But the principles that I try to teach are quite foundational across both of those things.

Curtis Duggan: It seemed some of the. At least one of the sessions that you MCed on the hot stage, the second stage were destinations that were aiming to market their city or region as a destination for remote workers.

I believe the one I saw there might've been more, I think there's Tefi was in the Tefi was there, but the one that I saw was Bueno Cyra. Gave a the city of Buenos Aires, a department of the city that had a mandate and a focus on attracting remote workers, traveled from Southern South America all the way up to Lisbon and made the trip and marketed themselves.

This has been going on a little bit for the last two or three years, but it felt like that was, This is the beginning of something and there's just gonna be more and more of that. First of all, I'm curious, how do you choose where to go when you're location independent? What's your kinda mo, everybody's got a different way of choosing where to go next.

And then do you think these destinations are doing a good job of marketing themselves for remote workers in turn, or their examples of where a destination has just knocked it out of the park in terms of communicating? Remote workers with remote jobs are welcome here. Yeah. In our town.


Jordan Carroll: Yeah. All very interesting stuff that we're seeing from governments, entities that are wanting to attract people to come there. I think I did a video actually a couple years ago on digital nomad Visas when they were first, like coining that as an actual term. And I was like, wow, we actually have a name now when we go through it our tourist checkpoint, like in an immigration, right?

It's For a long time, I'd have to say I'm taking a vacation, right? Have to tell whoever's at the immigration desk, like basically that I'm not doing what I'm doing, which is I'm working. I'm not working in your country, in your economy taking a job, but I am working here.

And so it was always confusing to know what to say to people when I think we're at a point now, what I really appreciate about the movement and like where we've gotten to. You can have easier conversations with immigration as you're passing through, or they just under, there's more of an understanding of what digital nomadism is in general.

Now are all comp, are all countries that are trying to do this, doing it well, no, of course not. And that's what Gonzalo's session was about, was how are the best, basically, hi. His was all around how the best governments. Are welcoming digital nomads, like what are the programs that are doing really well?

What are the programs that, need a lot of work? And I think we've seen over time, like I think Spain is an example where they had a digital nomad visa in, in, in a pathway to residency where they put this out. And then ultimately, like the tax structure of that really didn't make sense for digital nomads.

And digital nomads don't want to go somewhere and be taxed additionally. Yeah. Like they wanna be able to stay longer and just have the visa so

Curtis Duggan: they can Yeah. And that's been Gonzalo's point among other Yeah. Digital nomad thinkers in terms of the proliferation of digital nomad visas, to be blunt, they say they're, they don't like them.

I don't wanna put words in people's mouth, but I'm gonna paraphrase a kind of a thought, which is that. Many people are saying that the digital nomad visas are not really very good. They're not, they're more like remote work immigration funnel visas to bring someone from somewhere and commit to a second country.

So let's say it's an American or Canadian who. Fills out some paperwork, gets a digital nomad visa, and then comes and lives in Spain or Costa Rica or Portugal or the United Arab Emirates for a year, and then maybe renews for another year. And that whole way of thinking runs against what I. Gonzalo and many others say is that's not what digital nomads do.

We don't commit and immigrate to a country for a year. We might be there for six weeks and then six weeks somewhere else, and then six weeks somewhere else. So we want visas that support that for, I think that's a tougher sell just because of course countries are gonna want people that are.

It's like anything, you just they, they're gonna want something that feels like more of a win-win that lasts longer. Yeah. And they're gonna be less interested in serving people that are like, I just want free wifi and I don't wanna pay taxes, and I want to come for six weeks and then leave. So even though I love digital nomads and sometimes I am one I still think it's a tougher sell to get like the real visa, which is can I have a free pass to go around the world and never pay tax anywhere?

That's just. Yes. In a utopia that we'll all get to someday, that would be great. But it's a tougher sell. And I think every, I think Nomad should acknowledge that's a tougher sell. But Mexico did it. Yeah.

Jordan Carroll: That's why I'm here. Yeah. But that's the thing, is I consider myself a digital nomad who traveled around the world and at one point was in a different place every single month for a span of a number of years.

I ended up in Mexico because there's a lot of different criteria, and you asked about what that criteria was, and there's specific things that I look for in places that I go mostly. Sun walkability. Yeah. Restaurants, wifi, certain things like that. But yeah, this place specifically play Del Carmen, where I'm at, met all the smaller detailed criteria and then the country as a whole.

Has been very good to me as far as being here and made it very, in a relative factor, very easy to get a long visa. Like I basically have a renewal in another three years, and then I'll be a permanent resident here and Mexico and I've paid maybe a thousand bucks, 1500 bucks total. I, of course had to pass certain metrics on their standpoint. It's like how much money I had in my bank and things like that, but they made the process, and this was even really before all the Covid stuff was like in full swing. Like they still didn't really know what remote work was, but they were doing this.

So I, I think there's a lot of countries that can learn from that is you can convert people into being the, if immigration is ultimately what you want, like you can convert people. Make the top of the funnel easier. Yeah. For the people that are running Exactly. Ru rushing through for those six weeks, two months, whatever it is, because eventually they're gonna stop.

Like most nomads, like they travel for a few years and they stop. They say, where is it that I really fucking love being, and I want to create a base, like I want to go have a base there. Maybe I'll still travel, but this is the

Curtis Duggan: cycle

Jordan Carroll: that I've seen with all of my friends, including myself. It's like you get to that point where traveling in the month, Two month, three month increments gets really exhausting and you maybe wanna be somewhere for six months to a year.

Curtis Duggan: Yeah. And that's why there have been IMI immigration pathways since the Second World War and before that. But what's new now is the some core pressures and principles of competitive marketing Yeah. Are now applying. And exactly what you're saying about your experience in Mexico, which is, hey, yeah, maybe I'll get a lifetime.

Subscription. Maybe I'll get an annual pass, but don't make the free trial like a pain in the ass. Or I just won't. Yeah. I won't do it. Like I I gotta be there. I'll go somewhere else. I

Jordan Carroll: gotta be there in person. Like the gym thing, right? Where you gotta be there in person to cancel and you gotta oh yeah.

They just make the hoops really difficult to where people are just like, I'm not even gonna bother with that. I'm


Curtis Duggan: gonna go somewhere else. Exactly. Yeah. I, and side note on that, I was reading, I think someone said on Twitter about Planet Fitness, where they specifically don't have the Because I went through that, I had to cancel Planet Fitness, and I was like, you have to come in.

It was in a city that was two hours away. And they're like, you have to come in and tell us. And I was like I'm telling you now. What else do you need? And it's just, it's crazy what they, what the gyms do. And Planet Fitness specifically, I learned a second fact, not just that you have to come in to cancel, but that they don't have squat racks and various, benches and things that.

Regular users would use often because they want the kind, the people that aren't gonna use the gym very much. Yeah. It's a, it's a, it's, I'm sure it's a great business story, but it's a shitty human story.

Jordan Carroll: If you prioritize those, like what you may view as a short term gain of getting more getting, like if you get too greedy on that upfront piece and you don't look at the long-term vision, you might end up doing more harm than good. And I think that's what's happening with a lot of these programs. Is there, people are talking like the nomad community is very small, so if you want to get large swaths of nomads, you wanna get people that are the most influential people to come to the place that you're in, and you.

Fuck that up by making it really difficult for those people to go and they're gonna

Curtis Duggan: tell everybody. So maybe one more thing on this on this topic of what the competition between places. Another thing that's popped up that is I'm sure has always been there, but it, the media has been picking up on it, is the.

Is the local gentrification backlash, whether it's Lisbon or Mexico City, the idea of digital nomads go home. You don't contribute, you don't learn the local language, various accusations that I'm not saying I agree with, but at least that there, there is this point of view that's being reported on.

Have you engaged with that at all? Is there any part of that you've, spoken like, what do you think about that? All that stuff that's we're hearing about

Jordan Carroll: now? Yeah, it's true and it's unfortunate and actually, When I was doing an interview video of digital nomads here in Mexico, I did a counter video where I was interviewing locals about what they think of digital nomads.

The day that I was doing that, I had interviewed about 11 people total, and as I was starting the second, the second group of interviews, which was locals, I noticed that very few wanted to talk to me. So it was like really tough to get interviews. From locals. So this is a lifecycle of any city.

If you look at most of the major cities in the us, look at what's happened in the us. Most of the major cities are uninhabitable to most people like. You just can't afford you literally can't afford to even be anywhere near most of the big US cities. Yeah. And me included, like I, I don't wanna live in any of those cities and the amount of people that have been displaced there, it's like pretty crazy to see.

So I think humans are always gonna arbitrage. How they can, especially if they're from a first world country, they're gonna go to a third world country and they're gonna, they're gonna find ways to like influence that country to change their standards for them. And it's, yeah, it's a bummer because a lot of the cultures lost, and then the locals can't afford to be there. But I view this as kind of natural forces of economics.

Curtis Duggan: Yeah. I sympathize with rapid quote unquote gentrification or just price changes in the cost of living in any area. But I think. For me personally to take a stand on the side of the people who choose to move.

I don't think we should. I think it's a bot, a race to the bottom and a bottomless pit to go and start to try and judge if someone, let's say someone lives in London and they're like, I can't buy a flat. It's 4,000 quid a month. Yeah. I'm gonna go to Lisbon instead. So I can just, get a handle on my life while I pursue either my job or my business career and get out of the insanity of it costing, $10 million to live a life in London over the course of 30 years or whatever the total cost is, or the annual cost.

Let's say it's like 150,000 pounds and then maybe then you're not making that and you just wanna not be scraping by. So you go to Lisbon or this person goes to Lisbon and then all of a sudden, if they go and. If they have a remote job that they got from coaching from you, and then they settle in and they're like, great, okay, this is 1200 Euros a month instead of 3000 euros a month.

It's, great. Now I can I can at least afford it. I can save some money based on whatever I'm making. And then I. Someone's complaining this used to be 600 Euro a month. Yeah, the prices have gone up. It's what was that person? Are we gonna, are we just gonna force people to live where they lived in their own neighborhood at whatever price it is?

Because if they move, they're suddenly a gentrifier. And so I do firmly come down on the stand that like we cannot. We can't take away people's freedom to move these places. Of course, there's places you can't go. You don't have freedom to just go to the United States without a visa and start working.

You'll get in trouble. Same with China. Same with a lot of places. Where countries are saying, Hey, we're open. We're ready to accept people. I think that's what it is. And people are going to come and as a gesture they absolutely should try and learn the local language.

I think there's lots of nice to have benefits about that but also just if someone is speaking Cantonese in Vancouver. No one in their right mind who's a, polite, upstanding member of society in Vancouver would go and be like, Hey, speak English. That would be seen as very racist, very xenophobic, and definitely not done.

And so similarly, I think if someone's speaking English in Lisbon, they should learn Portuguese. It would be nice to do, but they also don't deserve to be harangued. If they happen to speak English and they don't speak the local language. So I'm not, I'm trying to not be, I think we're similar.

I don't wanna put words in your mouth, but I definitely come down on the position of. The reshuffling is gonna happen. It's just, yeah, it's, and it might be messy for some people who expected something to be a certain price. Right now I'm in I'm back in Canada, my home country, not really no matting right at this moment.

And things are more expensive here. A, a head of cabbage is eight bucks instead of three bucks or whatever it was. Eggs are more, everything's more, there's inflation here, so I might make choices about whether this is the right thing versus somewhere like Madera or. South America or Costa Rica in the future.

And I would hope to be a good actor and not a gentrifier, but I think there's always gonna be someone who sees anyone who moves from quote unquote, the developed world to quote unquote the developing world as automatically gentrifier. So that'll be there politically that'll just be there.

Jordan Carroll: The other way you can look at it is, From a remote work perspective and from a even the playing field perspective, the amount of opportunity that remote work brings to people that work. All over the world to just work online as opposed to work in their local economy and then move somewhere. That's really where there's an equalizer here within skill and talent.

And obviously there's opportunities and privileges that people have that start them off at different points of a race or start them off at different points, close to whatever it is that they're capable of doing. But I think a society that has remote working options, that, that tells someone from a country who is a developing country, maybe is being gentrified, but tells them, Hey, you also still have an opportunity to log in, find income online and move yourself as well about and be able to earn more or earn from.

A laptop as long as you have internet, which most people have at this point, or a lot of people have at this point, I guess I should say most. But I think there's still an equalizing sense that remote work as a broader good for people who have traditionally been unable to access. Equitable work can actually log in online and make money online.

Curtis Duggan: Yeah I agree that the there are some elements of increasing or displacing inequality, but the vast majority of what's happening is a net positive by increasing freedom of opportunity for unimaginably better, greater freedom of opportunity exists now than 10 years ago or 30 years ago. Yeah.

For people all around the world to. Pick up a skill that is economically valuable and put it to work. Without having to move 5,000 miles around the world, or if they want to move 5,000 miles around the world, they can do it remotely from home or remotely from somewhere else. And that's just we don't know how good we have it compared to 30 years ago when there was no internet or there's virtually no internet.

Just looking at the time. As we get close to wrapping up here, I wanted to mention one, one thing I wanna make sure I didn't miss it. So I was watching your video, the interviews with the CEOs and their take your latest video, but also a few of your other videos. And they were awesome.

And I mean that in terms of the music, I don't even know if it's stock music or if you composed it, but the way that it was orchestrated and curated as well as the cinematography, the quality of the camera, it was like a breath of fresh air. Amongst, content that's on YouTube. So I'm just curious, like how long have you been specifically video editing and what is the process for creating one of your videos?

Maybe taking the latest one from running remote as an example. Do you have a team or are you just a, are you a wi an indie maker whiz that. Crafts it all yourself?

Jordan Carroll: Definitely not. Number two. Yeah. I appreciate it, man. That's, that means a lot because a lot of work went into that and a lot of money went into that video.

Yeah. Like it's almost embarrassing to say how much money I spent on that video. I've been making videos since I was in elementary school. My dad had a HI eight camcorder and I remember. Me and my friends would go play like jackass in the front yard and we'd set up fake ramps and we'd jump off our scooters into the grass and just act like we like busted up our faces and stuff.

And anytime there was in school, it was like anytime there was a video option, like for the group project, I would. Wrangle everybody together, like we're doing the video and create the script. I'd bring the video and everything, so that was cool. As I've grown older, I was like, wow.

Like that passion that I had when I was a child comes through when I'm creating now and I'm able to do it and it actually, it makes relevant sense to what my business is and what I'm doing. So it's just a creative outlet that becomes really fun. Over time it's gotten the process to creating it has changed so dramatically because, For many years I created just for fun and couldn't necessarily justify what I was spending on videos and how much I was making from them.

And there's a, there's a curve with that where it's like at some point the amount that you're investing is actually getting you the money back. But that's really hard, especially with YouTube and having, the amount of subscribers I have and the amount of views that I get.

It's nowhere near close in, in pure ad revenue or things like that. But the process for this one, and I think the short answer is I've had a team, I've had a team in way in many different aspects. I've had editors, I have videographers, I have a channel manager. I have all sorts of people that help me with this.

My main role is creative direction, like I created, The concept of this video, I created the script, I created all the questions. I reached out to all the people I coordinated with the videographer. I hired a videographer that I did not know in Lisbon, I just, this is

Curtis Duggan: onsite operating the account,

Jordan Carroll: obviously.

Yeah. So he's on site, he's operating, and that's his equipment. And he's also, he was also the editor too. So basically what happened was I gave him a storyboard that I created. Of the different shots. We went through, we got through all the footage. He sent me all the footage, just raw, and then I went through it.

I did timestamps for everything and decided where I wanted to put things and gave him some direction on the editing with exact. Let's put this here, let's put this here. So then he puts together the timeline. From the timeline perspective. That's when we start adding the music and have, certain choices of what kind of music go here, what kind of music goes here.

And I actually think that's one of the most underrated things you can do is choose good music. So we were we were using, hi, the one that he uses his art list, I think. It's it's a paid subscription based music. So I actually went through and listened to like dozens of tracks, found out which ones I liked, and then had him ramp up and down based on the emotion that we're trying to create.

Yeah, I have a big document, like if you saw it, you'd be like, this is like super overwhelming with basically everything from this video that I did, and. It was a lot of fun, but it was a shit ton of work. Oh, yeah.

Curtis Duggan: We'll definitely link this video in the show notes for sure, because just how much we've talked about it.

But yeah, a final comment as a somewhat of a music aficionado in some ways and, a sometime Logic pro user. The music you chose and selected it's like there's been this trend of a kind of ethereal YouTube style music that washes over travel content, digital nomad, remote work content, and other types of lifestyle content.

And your selections were. Maybe in the, maybe adjacent in the same genre, but they were better and they they pushed it into a documentary, feel like a movement was being captured almost like if someone was an investigative journalist doing something, I could picture some of the music underneath a net.

Netflix or H b o Max, whatever they call it now, type of documentary. Yeah I'll check out that paid service just 'cause. Great selections. Yeah,

Jordan Carroll: dude, I, and I took a lot of time with that because I, that's been one of the hardest things about being a YouTube creator is choosing the right music and getting access to good music.

Yeah. Like a hundred percent. And I wanted this to feel like a small documentary so to hear you say that and did you do sound design or anything or have any background

Curtis Duggan: in, the thing I do most is I just Create and produce like songs with my band. So it's mostly software. It's mostly actually live instruments and some syns and drums and that kind of thing.

So I don't do cinematic sound mixing and design so much, but I, I sit in with the cans on and figure out how to make a mix work when it's not working. And I know that, that can be really difficult. You can even just slapping in the track that you've chosen, it sometimes doesn't work.

And then you, how are we gonna mix? How are we gonna make this sit in the mix? So it's the right, yeah. Left and right pan volume, the dialogues happening, overlapping sounds from other things. And and watch the end of the video. I won't say why, but I'd like the end of the, what was at the end of the video too.

So watch the whole thing. Yeah. Yeah. I guess last thing we met at running remote. I've been to running remote twice, but frankly I haven't been to any other remote work or digital nomad. Events in person. That hasn't been a big thing for me. I want to do more of them, and 2024 is an intention. I don't know how many I'll do for the rest of this year.

There's some I've looked at, but I think 2024 is gonna be a bigger year for that. Have you been to other. Remote work or digital nommed specific events and how do they compare to what happened at Running remote where we were joking at the dinner we had in Lisbon about how there's both enterprise thought leadership and there's also I don't even know how to, I won't say exactly the words that we said at the dinner because it was like, it wasn't rated R but it was like, it was very.

What we were saying was like there's almost, there's the culture of enterprise remote work and everything it brings about best practices, how to work async, and there's also an undercurrent of exploratory remote workers and digital nomads who are going out and having fun and maybe exploring different experiences.

And those worlds collide just like a not quite like burning man, but it's just like Silicon Valley. There's board meetings and there's Burning Man, and there's an element. Yeah, there's a tiny little miniature element of like board meetings and Burning Man. Running remote. I'm not trying to, nothing crazy.

Go went on. We didn't go to any crazy parties, but there's just that undercurrent. So anyway, I got off track, but I was just curious if you've been to any other events run digital, no matter remote work events and how they compare? I have,

Jordan Carroll: yeah. This was definitely the most corporate one I'd ever been to.

And maybe that's saying something 'cause it's still. Even with the corporate elements of it it wasn't like overly corporate if you go to a regular conference, but yeah,

Curtis Duggan: I've been to some regular conferences in my yeah. My daylight. Yeah, it can be much more corporate. Yeah. Yeah. I

Jordan Carroll: used to work at I B M, so Yeah.

Curtis Duggan: You know it, yeah. It's like crazy difference. Even from that, the,

Jordan Carroll: the few that I would point to one would be Nomad Cruise. Nomad Cruise was my favorite event of all time. It was a con, it's a conference on a cruise, four nomads. There's about three or 400 nomads on the cruise. There's also other people on the cruise.

It's not only the three or 400 'cause I think cruises can hold, multiple numbers higher than that, maybe even in the thousands. So it was just so awesome for me because you could keep your phone in the room 'cause you don't really have service. You could buy the service, but it was really unreliable.

For ours, we were traversing across the Atlantic Ocean. So you put the phone in the room and you're on a cruise. Everything you need is all in one place. It's like you're lodging and accommodation. The conference, the food, like everything's just in that one place, which I really loved about it. When covid hit, they actually stopped doing the cruise and they did what's called nomad base. So they created on land events that were very similar to the nomad cruise culture, which is really focused around like having fun learning growth, but then also like that undercurrent of let's do some experimental shit.

And I really love that about that community. And then the more. The other one would be Dynamite Circle. Dynamite Circle is entrepreneurial focused. So whereas in Nomad Cruise Nomad Base, you're gonna find a lot of people who are maybe employees or freelancers or, people that are maybe on the lower not lower, but earlier journey in entrepreneurship or earlier, earlier journey in their nomad thing.

Or they're just employees. Whereas Dynamite Circle, there's actually a a. A bar that you need to meet with the income that your company generates. And it's for location independent entrepreneurs. So it's a little bit more business focused where, and what I mean by that is the people in the room.

Have a much higher level, like you meet people that are running 50 to a hundred million dollar businesses and are, but they got fucking flip flops on and shorts and and a tank top and they're, you're

Curtis Duggan: drinking at the bar with them doing whatever. So there's an expectation that you might work remotely eight hours a day.

And wifi was just, it's just fun. They tell you

Jordan Carroll: on time, they tell you take the time off. They recommend that you take the time off. They recommend that you don't buy the wifi

Curtis Duggan: because it's, Yeah, very explicitly. Not a workation with a eight hours of work. Okay. Maybe it's a bit of a cliche, but I'll do a quick final lightning round question.

Is there a place in 2023 this year you haven't been yet, that you're excited to go to next, or a top nomad destination on your wishlist for the rest of 2023 or 2024? A lot. Yeah. Yeah. I couldn't tell whether that pause was like, Nope, there aren't any. Or there's too many.

Jordan Carroll: I was thinking in my head, I was like, okay am I actually going somewhere and I am going back to the states to visit my family, but I didn't have, I.

Much other plans than that. Funny enough, like the Buenos Aires folks came and spoke and

Curtis Duggan: they didn't, they sold you. I've always been, I always wanted to go to Buenos Aires

Jordan Carroll: and yeah. I really think that would be a fun place to journey to. And just randomly, I've always wanted to go to Japan.

Curtis Duggan: Yeah, Japan would be great. And I've heard that South Korea and Japan are starting to, I, I saw it like in a line of someone's newsletter that they might have remote work. They're usually, I don't wanna say closed off, but they're, yeah, they're not typically places where it's easy to immigrate to.

I think that's a fair statement. So we'll see how they handle a bunch of digital nomads that aren't Japanese, aren't South Korean coming and staying, and whether they have full on digital nomad visas. But yeah, Japan would be great. And I agree that. Buenos Aires sold me on, oh, yeah, that'd be fun.

Okay. Yeah. Maybe I'll go there. But yeah. Okay. Yeah. Bueno Aires. I'm gonna, I'm gonna research more and I hope actually to talk to Maro, who I talked to from the Buenos Aires team maybe on this podcast and learn more about it and plan a trip there. But thanks. Thanks Jordan for coming on the pod.

I really appreciate it. Have a good one.

Curtis Duggan

Curtis Duggan

Curtis is a serial tech entrepreneur, content creator and the host of the Remotely Serious podcast on the future of remote work and digital nomadism.


Great! You’ve successfully signed up.

Welcome back! You've successfully signed in.

You've successfully subscribed to Remotely Serious.

Success! Check your email for magic link to sign-in.

Success! Your billing info has been updated.

Your billing was not updated.