Engineering a nomadic lifestyle: a conversation with Grayson Harris

Engineering a nomadic lifestyle: a conversation with Grayson Harris

Full Transcript


Curtis Duggan: Hey everybody. Welcome back to Remotely Serious. My next conversation is one I am excited to share with you. It's a conversation with a digital nomad Grayson Harris, who has not taken maybe the typical approach or doesn't fit the typical stereotype about being a digital nomad. He has an engineering job that he has simply taken remote.

He's not trying to be an Amazon Dropshipper or a blogger or a YouTube influencer necessarily. He's someone who has simply taken a typical job that you might find in any city around the world a really good engineering job, and he has. Moved his life to be remote first, and he's continuing to work for his job and living the remote lifestyle.

So we get into how that happened, why he chose that life and learnings that he's had in pursuing this path. So let's jump right in.

Hey everybody. Welcome to remotely Sirius. I'm here with Grayson Harris. We actually, we met at running remote recently. I guess it's a couple going on two months ago, maybe not quite two months ago. We met in Lisbon. It was a beautiful sunny day. It was a sunny couple of days there, if I recall. And yeah, grace, we met on the patio and I I'm excited to talk to you because I think there's a certain perception of what kind of job or what kind of path a remote worker has taken.

You, you mentioned you worked in engineering and power engineering and those were, when I think of those kinds of firms, they're not the ones that jump out as maybe the first ones to jump on board with remote work in 2020 or even earlier or later. I'm just curious maybe how long have you been a remote worker and maybe do you consider yourself a digital nomad and, what were you up to before coming to Lisbon in late April of 2023?


Grayson Harris: Yeah, first of all, I'd just like to say thank you for, bringing me on the pod and it was definitely awesome connecting with you at running remote. That was pretty awesome conference. That was my first time there and I really just love the community of the conference. Everybody's extremely welcoming.

It was great just to meeting other remote workers, digital meds. As far as myself, I definitely identify as a digital med for about two years now. You're definitely right. I think at the conference, I don't think I met on a person in my industry in

Curtis Duggan: most, what would you call your industry? I said power engineering, but I wanna make sure I get it right.

Grayson Harris: What would you Yeah. Power engineering, like the utility industry. Yeah. The energy

Curtis Duggan: industry. So something that jumps out as I'm not talking about your employer, your firm, but stereotypically it jumps out as one where the conversation about remote work might be a bit awkward. It might be some older folks with a lot of experience getting stuff done.

At whiteboards and around, AutoCAD on monitors in an office. So what was the first ever conversation to become a digital nomad or a remote worker, like with your employer, if you're able to share that?

Grayson Harris: It's a really good question and it's a long story, but I can give you the highlights.

It's kinda serendipitous and stuff, during Covid there's kinda two types of companies, right? There was the company, like my previous employer, which was, Hey, remote work doesn't work the second we can get back into the office. We need to, and then there's companies like the one I'm at now, which, they went remote and then they saw this potential benefit like hiring people across the US instead of just in Denver where it was located.

And, yeah. And like I said, I was at a previous company that really wasn't into this whole idea. I had actually brought up doing something like a digital nomad. In January, 2020. They said no remote work doesn't seem to work, but maybe in a few years, we'll think about it, but really no.

And it was funny. Basically around that same time I was at the locker room of a gym and just talk with some people how, I love to travel and would like to live abroad, but I think I needed to get outta my industry to do that. And the guy's oh, what are you doing?

I'm an electrical engineer and the guy behind me. Says, oh, where do you work? And I tell him and he's okay. And ended up, he worked at like a direct competitor of mine as like the president of that company. Fast forward to August, 2020, and he messaged me out of the blue on LinkedIn, seeing how I am if I'm been able to travel yet.

And we started the conversation. I basically say, Hey, you know what I want to do, and Basically the agreement was after six months of working in the office or from home in Denver, I would be able to start nomad. So you switched,

Curtis Duggan: Jobs to to an employer who was able to give you a, I won't say hybrid deal, but they gave you a trial period in the office, and then after that you were able to go work around the world.

How did you choose your first destination? Are, were you in, in Colorado while this is happening? You're sitting, you're working, you're going to an office and the talk the clock's ticking five months, four months, three months from now, I'll be able to go anywhere. How, what was that like?


Grayson Harris: So the timing was about May, 2021. So anywhere's a little bit relative. Because the world was just opening back up from Covid at

Curtis Duggan: that time. How quickly I forget. Oh yeah. It was 2021. You could just go anywhere. Absolutely not. And

Grayson Harris: I pushed it from my mind. Yeah. That's another reason why I had that six months is.

That was part of my proposal to the company. It was for a few reasons. One was nothing was open. There's some other reasons, right? Kind of building camaraderie and stuff like that with people on my team. But really I just kinda looked at what was open. My best friend who worked at the company last minute decided, Hey, I want to go with you.

And we really were talking about Europe and Croatia was about the only country at that time that was open. And so we just started there and really the first few months was navigating, everything as it was opening in Europe.

Curtis Duggan: Did you know about Croatia as a digital nomad destination, or was it more that you knew about the country for other reasons?

I just know that because cities like Dubrovnik and Split and other regions of Croatia are actively looking to market themselves as nomad destinations and remote work destinations. So I'm curious if you just. Knew about it from being younger or thinking about it? Oh, I'd love to backpack through Croatia, the association with backpacking through Europe or did you get specific marketing or receive specific marketing saying this is a good nomad destination, or it's just the, it's the happenstance of, it was the only country that was open and better will be cool to go there instead of Asia or somewhere else.

'cause I guess Asia was also closed

Grayson Harris: and Yeah, a lot of that was closed. I think Asia was still pretty much closed. South America. It was pretty random. Some places were completely locked down. Other places started to open up. It was really the latter. It was really just Hey, we want to go to Europe.

Someplace. Started talking about opening, like Reese was talking about opening. That's where we ended up going second, but at the time it was really Croatia open. So let's try it out. I haven't really heard anything about it. Where'd you go first in Croatia? We

Curtis Duggan: we basically the month in split.

And was that. In the old town or did you how did you find your accommodations?

Grayson Harris: Yeah. It was in Old Town, did the whole Airbnb thing. Lived together with my buddy to kinda get a little bit of a nicer place in the best location. Yeah. And I just like I said, the next few months in Europe, we really just navigated what opened.

We did Greece and in France. Pretty interesting time to be a nomad. But it was really awesome to kinda be able to experience it. So you're,

Curtis Duggan: you're based in an Airbnb in the old town of Split, and for people that don't know this it's on the Adriatic Sea near several, an Archipelago, I dunno how to say that word, ar archipelago of of Croatian islands.

That's essentially across the way from the east coast of Italy. And so you have this Balkan Adriatic, Adriatic coast of Croatia and Montenegro, and eventually, Albania and Greece all the way down. And so you're in this old town, you can picture it, Dubrovnik old walls are maybe a more of a famous picture, but Split also has an amazing old town and a Roman emperor's palace.

So when you're getting acclimatized there, and you're also, I assume have, eight hours of work with your employer doing engineering, I assume on a laptop with probably some. Data writing and maybe some visual intensive work for the line of work you're in. How was that first week of being in a Roman emperors palace old town, in an old European city, but also doing work for your employer?

I. I

Grayson Harris: Remember back to, I think my very first Instagram post when I was like, nomad was, started the weekend homeless and ended up in a palace, right? And it was just a crazy turnaround. I think just that very first week, me and my friend were just like, yeah, this is it. This is what we wanna do.

Love. I. That independent like location, independent lifestyle where you can say, Hey, I wanna live here for a while. Or, Hey, I wanna try out this. And being in split you get the the history and stuff like that. And especially at first, I've evolved a lot as a digital man over the last two years, but at first you just wanna do every single.

Thing like every single day, you're go working, the eight hours or really my first couple months I was working extra to prove that I can do this. And at the same time, then all your extra hours are, we're, we need to do this, we need to do that, we need to hit everything right.

So the first month or two are pretty crazy. There's that

Curtis Duggan: inclination in the first days of a new arrangement with an employer where you almost. Overwork or do a couple extra hours or maybe even get, stay up late or get up early on whatever the different time zone is to just to show that you are definitely, it's still totally normal, still totally working.

And then I think over time you evolve the trust where you might be on a different time zone and that's okay. And you negotiate the overlap. And of course, each company is different case by case. Some want. Synchronous overlap. Some are okay with Async. Maybe jumping forward, what are the biggest things that have changed for you as a nomad from the first couple months where you were sharing a place to now?

Have you, is there anything where you can just point to something and say, it's just so different. I thought I should do this, or I thought I it would be best to do this Now I know that's wrong. I do things a different way for sure.

Grayson Harris: There are a ton of things. One of the big things that come to mind is just.

Kinda relaxing and understanding. No matter how long I'm in a place, whether it's a week, a month, two months for me, my list only gets longer of the places I wanted to visit. I can maybe check some off and sometimes I, I check some off more than others, but always when you're there, your list is gonna get longer.

So you're always gonna have that fear of missing out, that fomo of not doing this, not doing that, but really to me, that. The thing that changed with that is feeling like I'm living in a place and not traveling. Yeah. Because there's a very different mindset with that. It's like the first few months, like I was saying, it was, I would go to the gym three times a week.

The other two mornings it was, okay, I'm gonna do this museum or go walk around and do this. And now it's really just, I want to go over here. I wanna surf I wanna go to Brazil and surf a few, for a

Curtis Duggan: month. Did you pick up surfing as a Noma or had you already done it in the United States?


Grayson Harris: done a little bit in the US growing up, and then for me, I'm kinda a hobby junkie. It's one of my favorite parts about Nomad is saying, oh, I wanna go here. I wanna surf. I went to the Dominican Republic and about to go to Peru, coming up to Kite Surf. Yeah, that's always something I wanted to try or hiking, I can just say, Hey, I want to try this, or, Really do this for a while and picking a place just for that.

One of the things I'm really trying to do right now is focus more on these hobbies slow down a little bit and really go for more of a purpose to places.

Curtis Duggan: Yeah. I foresee I. A type of workation. And I don't think it's really, it's, I don't think it's really taken off yet, but I think it's taken off in small ways.

Maybe it's still quite a niche. There are certainly workation packages. I'm using the word workation. I don't know if it's totally familiar to all the listeners, but just the idea that if we think about a workation, it's where you, on a typical tourist group package, you might go somewhere for three weeks.

It's a. European tour or a cruise up to Alaska from Vancouver, from Los Angeles, or it's a Caribbean island resort, all inclusive. And you go there and certain things are taken care of, whether it's travel or food or all the food for two or three weeks. There's variations on the all inclusive vacation, the group through Europe.

Sure. And a workation is an emerging concept where the same kind of curation is done, except there's the provision for people being able to work. Six to eight hours a day. There's the understanding that people aren't there to pack their full day through of activities and hit the things on the itinerary, but the understanding that the attendees will need quiet, good wifi coworking space and they will need the time to work, but that in the evenings and weekends they've signed up for something where they want to see.

Argentina for a month, or Belize or Bulgaria for two weeks, and they're there for a workation. So I say all that as a preamble about Workation in order to say, I think there's a step further in Workation where there is the connection to the hobby, like you mentioned. Where the goal of a month long workation in Sao Paulo.

Or in Madera is to learn Portuguese or be functionally fluent in Portuguese by the end of two or three months, let's say. Maybe, probably can't learn the language in two weeks, but let's say after three months. And there's structure around that and it's almost it's a, some of the video gamification of life in a good way, I think where you're saying my quest when I'm, on this particular vacation is not just to be there and it is to live there, but it's also to learn to kite surf or to improve my kite surfing.

Individually. I think most people will still live their lives individually and go do that, but I'm not sure actually that, that's a good segue into have you ever done anything where you are going somewhere and signing up for something or doing a workation or a month long stay or week long stay that is a group event?

Or have you been a solo. Or with your friend the whole time. It's really,

Grayson Harris: really mixed. To be honest I've done a lot solo. I've done a lot with my one or two best friends. I actually just finished up two months with my dad. Oh, wow. Which is pretty a unique thing. Yeah. So it really depends on what I'm looking for.

And, Kinda have that, those friends that you really want to travel with and go on, go out of your way for. Otherwise it's just, Hey, I wanna try this hobby. So another one I did was me and my best friend went to Belize to scuba dive for a month. Yeah. Just like you're saying with Spanish, one of my friends, we really wanted to learn Spanish.

We did too much in INE doing Spanish classes almost every single day. And I really think that's a great segue. For people that are maybe working and maybe they're curious about the nomad life or they just want to get out. For me, in Denver, I love snowboarding, but also once it gets to about March, I'm sick of the coldness.

So just go for a month and warm up, go to the beach, go surfing, try to scuba diving, and I think that's a great way to try out the life as well. Almost like a test

Curtis Duggan: run. How has it been with your. Work setup. So are you taking one laptop everywhere and flipping it open? Or does any of the nature of your work demand that you.

Need anything more than that? How has that been? Yeah, I like to

Grayson Harris: think I'm a minimalist in a lot of ways. I'm not as bad as some people. I've seen some people travel with three monitors and stuff like that, which is pretty crazy. Yeah. I do have another, a small monitor. It's like a, it's a graphics tablet.

I thought at first I would kinda have to use that for my job, and now it's just a second monitor, but it's really just a laptop. A little monitor. I take everything I need for work in my carry-on that way. Worst case scenario, which has happened once, if your suitcase is out for a couple days the airline loses it.

You still have everything you need to work. So you're not gonna be missing out. You might just need to get some new clothes for the few days.

Curtis Duggan: Then I know this is like going through, I think this is interesting to our listeners is going through the minutia. But I'm just curious also you're American and in the United States there's a big thing around healthcare being tied to the employer.

How did you navigate healthcare or health insurance while you were going to many different countries with different health systems?

Grayson Harris: Yeah, it's a good question and. I think it's one of those things that you really need to decide for yourself. There's a lot of options out there for digital nomad kind of healthcare.

For me, my company, it covers me for emergencies abroad. Yeah. Whatever that is determined by the insurance company. And so far I've just stuck to that. What I've found is for the couple of times that I have gone to the doctor for tests or a little bit of sickness here and there, it's really never been.

Compar to the us nothing that's broken. The bank, and I remember I spilled hot boiling coffee on myself in Dominican Republic. Had to go to the emergency room. It was about 60 US dollars,

Curtis Duggan: right? Yeah. Yeah. There's, this is not medical advice for any of our listeners, but there's lots of nomad thought leaders and folks that will just say, especially if you're in places like Mexico, Columbia, I shouldn't speak too much of it if I don't know the precise details, but, Suffice to say in many places the recommendation is you can just pay cash and you'll be okay.

Again. I don't know. I'm not saying do that everywhere. In fact, you probably should do your own research, but yeah, it's interesting. Has there ever been a place where you showed up for any reason where you quasi committed to it via, maybe you bought accommodations for two weeks or you. Got a coworking membership or something for a week or two or four and it just turned out not to be what you expected and you either had to scramble to find your happy place for working or you had to change your accommodations.

Is there anything where the nomad life posed challenges and it wasn't all rosy?

Grayson Harris: Definitely. There's a lot of things that come to mind. I think one was, again, kinda going back to the initial travels, one of my biggest flubs it was late 2021, I was going from Turkey, supposed to be going to Italy, and last one of the day before I realized that there's two countries in all of Europe they can't travel to from Turkey and Italy is one.

So kinda scrambled. I was trying to do maybe like a cheap place, just lost that money for rent, unfortunately. And so I decided upon Poland this is.

Curtis Duggan: So sorry. Was the problem, like you, you literally can't, you can't, there wasn't a direct flight or you can't get there

Grayson Harris: somehow? No, it was the the Covid regulation.

Oh, I see. You just literally can't, Turkey could not go. Yeah. It was a red list just for Italy. Not the rest of the shein zone or Yeah. Or anything like that. So I decided to do Poland in the beginning of November. Or excuse me, been in December. And keep in mind I really was traveling for summer and the Poland in December was quite cold.

Yeah. I luckily got, went to a thrift store and got like a big jacket, but that was probably one of those months where I said I love raca, I love Poland. But for me, at that time it was not my favorite. And I just rolled with the punch for the rest of the month. But that was definitely one of my bigger flubs.

And it is definitely by no means all rosy in this life.

Curtis Duggan: So you've been doing this and all this time, you're living your life. You're probably feeling like you're learning a lot of things and getting access to almost it's kinda like getting access. Not to a secret society, it's not a secret at all.

It's totally out in the open that these, this type of lifestyle is possible. But you still start to observe things. I find you start to observe things that put perspective back in put life back home in, in perspective. And it can often feel like. You're doing it alone or you're learning on forums or you maybe think how is I'm around all these tourists, or I'm around the locals in Croatia.

Where are all the other digital nomads? And so I'm just curious. I. Did you meet other nomads besides your main friends as you traveled, or did you feel like you were going through it on a solo adventure or with a couple friends, but did you feel like, oh, I've arrived I've found the other nomads in the community and we all hang out.

Did that kind of thing happen?

Grayson Harris: Yeah, it's a great question. So my first three months I was with my best friend and. Admittedly, I really meant no other nomads. I didn't go to a coworking. I didn't really try and put myself out there, to be honest. I was enjoying the time with my friend. Yeah. And we made some travel friends, but really no other nomads.

So my first month solo, I went to Bulgaria Varona. It's on the Black Sea for the summer. Went to a coworking and it was just like my life completely changed. I was, I remember being the, this coworking for the first time and I would take out my headphones because. Coming in my industry the conversations I would hear, in my old cubicle in office were very technical, maybe a little boring, where also these are completely new conversations of entrepreneurs helping each other out, different stuff like that.

And I was really exposed to the nomad community there. And really since then, a coworking has been one of my must haves when I go to a place, I actually don't like to work from home. I'm a. And on Digital Nomad where, he doesn't like to work from home. He is, he's at a co-working.

I'm at one right now in, in Serbia. And yeah, so that's a must have. And really finding the community is huge for me, even if I'm traveling with a friend.

Curtis Duggan: So did you find the kinds of people that were working at the co-working space is. Were in startups and tech. That seems to be a stereotype that a lot of digital nomads are entrepreneurs doing tech, and that wasn't necessarily what you were doing.

What was your, what was that kind of acclimatization to this subculture in the coworking spaces, like once you started meeting people?

Grayson Harris: Definitely, yeah. I would say I'm still a unicorn. And I've met actually a couple people in my couple years that are doing something similar to me, but it's very rare in my experience.

A lot of people, especially at first were the entrepreneurs bloggers small time influencers or they own some agency, something like that. I. As time has gone on you are finding more of the nine to five nomads that I call and there's, different forms of that as well.


Curtis Duggan: I might just get on my soapbox for one quick second and say that I think that there's a. Absolute fallacy. There's a total myth around becoming a digital nomad, or the concept of a digital nomad, or even a remote worker is that it's all packaged up with, oh, so you wanna be a digital nomad? Okay, go start an Amazon drop shipping business, or a D two C Instagram brand, or a blog or a, or build an iOS app.

And become an indie hacker or startup founder. And become a digital nomad. I think that's changing a little bit, but I would say, first of all, unless you actually really want to be an entrepreneur, you don't have to be, it's not for everyone. And no one should think that they need to do that in order to be like, an a digital nomad.

And the vast potential for digital nomads and remote work is to be able to. Work for whatever job makes you happy and is what you want to do in life and work remotely. And that should I shouldn't, I don't wanna say should, I'm not saying anyone should do but there, I think people could be open to the fact that the future of remote work is just people, the millions and millions of people that don't want to be tech entrepreneurs, which is most people.

And we're in a big tech procession right now. So I think it's a sweet life to have a job you like or a job you love. The ability to remote work and then go live life. And I'm just, I'm making that public service announcement right now because I think that there's too much wrapped up in Instagram, influencer slash digital nomad slash traveler, and that's just.

That's nothing. That's just Instagram. That's Twitter.

Grayson Harris: Yeah. I couldn't agree more. I know, like you said it's going away a little bit, there's always a thing where you need to do what you love and you need to have the lifestyle that you love. And so to be a digital nomad, you need to quit your job, need to find out what you love and do that, and then you can do this lifestyle and, that's awesome if people can do that.

But not only are you asking somebody to completely change their lifestyle, you're also asking somebody to completely change your occupation, right? And not everybody can be an entrepreneur and. That's just a really hard two things to do. So maybe you do wanna become an entrepreneur one day, myself, that's something I'm thinking about.

But use your current job to get the lifestyle that you want and maybe you're good with that. Maybe it solves everything, the problems that you thought you had, maybe down the line. Then if you want to be an entrepreneur, you can take that next step. You don't necessarily need to do, you know everything all at once, for sure.

Curtis Duggan: Yeah. If you think about, if you were going to make it a sudden dietary change and up your workouts from once a week to seven times a week and learn a new language all within a 60 day period, I think that's what some people are trying to do. If they right. All at once, quit their job and launch a personal brand and try and launch a profitable or growth business all in one fell swoop of a big cleaver that comes through their life and cleaves off the past life and starts the new life and some of the influencing.

I, I think it, it is going, it is evolving and there's more. Pragmatic advice out there. Yeah. But, and it's evolving, but there's so much, this is maybe I'm maybe fighting the battles of 2020 and 20 21, 20 19 in terms in earlier in terms of the digital nomad marketing. But yeah, I guess so. You, but you like to go to coworking spaces.

You're acclimatizing to these new types of people and just. There's a self-selection bias around people that have chosen to go to Bulgaria or Serbia or Metagene and work in a co-working space. It's just it's like going to New York or going to London or something like that or going to a rural area.

There's people that wanna live in the big city. There's people that wanna live out on the farm, and then there's people that want to go to Bulgaria and Serbia and Med Gene and work in coworking spaces thousands of miles from where they grew up. We met at running remote. And I actually think that that conference I, I went the first time in 20, what is it?

It's 2023 now. So the first time I went was in 2022 in Montreal. I'm Canadian, so it was in my home country, although I still had to get across the country 'cause I'm on the west coast. Hour and I was on the West Coast at the time. Did you, w was this the Lisbon edition in 2023, your first running

Grayson Harris: remote?

It was my first in person. Technically I kinda last year won a free ticket to the virtual. A free virtual pass last year and I really started watching some of those sessions and that really, I was like, oh, this is actually really cool. This is really related to a lot of the things that I'm kinda looking to change in my occupation and that I'm more interested in.

And so I I. Went from that to say, okay, I'm gonna definitely be there next year. So

Curtis Duggan: the content around how enterprises can, the various talks. So for those, if you haven't listened to previous episodes or you don't know what running remote is. Running remote is a conference that have been doing it, I think since several years before the pandemic.

I don't know the official inauguration year, but essentially the programming. Is centered around bringing in essentially the best thinkers and speakers in enterprise remote work that are talking about best practices for working async, how to lead a team, how to create an HR strategy, how to do hiring and firing, how to.

Make sure the culture doesn't get scattered because everybody, 'cause everybody's all around the world how to do on-sites and retreats every quarter. And so it's not, I'm making it sound like it's really didactic how to do this, how to do that, how to do that. It's actually quite open-ended.

There's lots of panels. It's very charismatic and fun and interesting. It's not do this. And I think that there's a mix of people that go and so it sounds like you are, is it the kind of thing where you are. Listening to these things with a direct line back to I wanna bring this into my organization with my employer.

Or is it more, it's interesting intellectually if and, but it may or may not be that you advocate for all this stuff back at your employer. It's just a personal interest.

Grayson Harris: Yeah it's for sure the first I'm really trying to bring a lot of these things back to my company.

I guess we're taking a step back just. Living this life, I've really, I love this lifestyle and remote work lets me get there, right? And one of the things that I had to do was changing how I work. So when I started in Europe, I was three hours of overlap. I didn't have let down to zero when I was in Asia and kind of change had to change how I work for that.

And so I was starting to do some of the kind of remote work best tips just in order to survive, right? These async things. I was kinda looking for any information I could and just with this lifestyle, I just became really passionate about remote work and trying to bring these things to my company, which is an agile one for our industry, but we still have, a long ways to go.

So that I was really trying to get some big takeaways from the conference and, from these leaders in the tech industry. In industry, we can't necessarily move as super fast as some of these. We're not gonna be implementing AI tomorrow to take over all these different things in our company, but we can implement a lot of these other.

Things that people are talking about at running remote. And that's definitely something I'm trying to bring back to my company right now. I

Curtis Duggan: wanna imagine a listener to this podcast who's, maybe they're driving in their car, maybe they're on their commute to work at the office and they hear something like, I.

I had zero hours of overlap in Asia and in their mind they're listening. If this is you, if you're listening, just we know you're there and we're talking to you and we and what I want you to do Grayson is almost imagine, is there something I. Tangible from going async. So again I'll define this term again for the listeners, just 'cause we've used it a, I think I've used it a couple times where you've used it a couple times.

Async, which is short for asynchronous I is a term to refer to a mode of work where it's not assumed that the classic multiple meetings per day or multiple meetings per week are happening on the same time zone or even in the same place. It's assumed that various tools like. To use a simple example, Google Docs or a project management software is being used and people can contribute to visuals, designs, deliverables collaborations, what have you on their own time.

So you wake up, you're in a different time zone, and then you see some notes have been left on something that you proposed eight hours ago. Three of the decision makers have weighed in. Okay, great. I didn't need to have a meeting with them 'cause I did some really great documentation, made my case. I may have even recorded a video of myself explaining some of the finer points with a whiteboard that's captured by a screen capture.

And then they gave me my decision and boom in, we each spent 10 minutes logging in on our own time and then, We made a decision and we didn't need to have a one hour meeting with donuts in, in the arbutus room, or, some boardroom at the office, the Douglas fur room or whatever.

People are wondering, like, why did you say that? I, in the Pacific Northwest, there's, I remember growing up there was always these rooms that they would name after trees. Like an important room would be the fur room. Our bud, our buds is a tree in the, I don't think it's, I don't think it's across the world that much, but in the Pacific Northwest, there's our BEUs trees.

They have like bark that. Peels off like skin. Anyway, to circle it back, there's this listener who's like you. You had zero hours of overlap in Asia. There's no way that work can get done with, without meetings, without the even without just being on chat at the same time. Is there any kind of, Tangible thing, even like a specific piece of software, a specific habit that you learned while you're on a really different time zone that got you from, maybe this is really hard to, hey, this is easier or better, or, work functions.

Async, is there anything from, you mentioned Asia was, is zero. Zero hour overlap, right? No overlap with North America. So what's the journey there from zero hours to I'm functioning and this is working even though we don't meet necessarily every day. Yeah,

Grayson Harris: man, it was a pretty awesome journey.

And speaking to this listener that we're talking to, you might not be able to do zero hours of overlap right now, where I'm at. That's probably not super realistic either, but you can probably do less than you think, and some of the ways to get there are. Being proactive. This is one of the biggest ones.

Seeing what you're going to be doing the next day. Getting ahead of that, making sure that you know the people that are doing work for you have everything that they need. What you need from people. You're getting that way ahead of time. Predicting you can get to a level where you're predicting whether people need from you.

So if you need a, you can set that up. You mentioned it, but loom using looms or these little videos where you can share your screen and talk out some complex things, which for me, an engineering I was using a lot. So being proactive is a really huge one. Another one that comes to mind is low context communication.

When you're in zero hours of overlap in Asia, if I tell somebody to do something for me and I don't explain it, they're gonna get in and they're gonna say what? Or be confused, do the wrong thing, maybe not do it at all. So using low context communication, really almost overexplaining, assuming the person you're talking to, doesn't know this at all.

So taking that little extra time to really read it over over explain a little bit is gonna save a ton of time in, in the backend as well. Nice.

Curtis Duggan: Yeah. Exercise over. That's, it's been really helpful for our skeptical listener who doesn't believe that async work. You're free. You know that listener.

You can relax now. We're not targeting you anymore. We're not thinking about you anymore. We just wanted to speak directly into the microphone to you for three or four minutes. Now that you're several years into this and you're con, continuing to work for your employer there, there's not some, you're, entrepreneurs sometimes get pulled to where their market is or there's something that pulls them in a certain direction.

You truly have kind of this link to your employer and then complete freedom. Again, maybe not complete freedom. There's various. Countries that are closed or open, but there's more countries that are open now in 2023. Do you have a sense of how long this mode will go? Did you think of it like, This is forever, or this is just how I live now?

Or is it more something that's you're, I'll explore this and continue to do it for several years. And then as some people like to phrase it in this subculture, I'm going to quote unquote find a base. People talk about finding a base, oh, I'm gonna find a base in Portugal. Yeah. I'm gonna find a base in Central America.

Does that terminology resonate with you, or is it just, Hey, I'm from the us. I might go back there sometime, but I'm just traveling.

Grayson Harris: Yeah. Right now, I'm really just wanting to keep going and I really don't ever want to not be location independent. I don't ever want to be in a situation where, Hey, you have to live here.

I think I'm eventually gonna get some home bases around the world is the fantasy, but really right now I'm continuing on, I think. I just reevaluated actually pretty recently and how I want to move around and I think I'm gonna start, doing two, three months in a place where typically I'm really just doing a month, so start slowing down a little bit and I think it's just gonna change like that, maybe it's gonna get to six months in a place, or a year or six months, one month, whatever.

Yeah. I think the big thing for me is just. Is maintaining my location, independence and also asking myself how I'm feeling. Right now I'm definitely wanting to slow down for a couple of reasons, but then I'm, maybe I'll wanna speed back up again. And I think just really checking in with yourself is a huge part of the digital medlife that we can get away from, but really making sure you're aligning with your priorities with

Curtis Duggan: that.

There was a, something I noticed at this running remote that was I think it might've been there, Montreal, the year before, but I, it felt like it was a growing. Trend, which was the destinations themselves coming and marketing their destination as a attractive place for remote workers and digital nomads.

So Buenos res was one of them. The island in the Spanish island was another one of them. If we can indulge in one more exercise of imagining the persona of a listener. Let's just say one of these, we'll call them tourism marketers. It's not really tourism. One of these ministers of tourism or destination marketers Yeah.

For digital nomads and remote workers is listing right now, let's say that they're the mayor of our, of a fake city. The mayor of a place, a city, let's say a city, not a country that is, they just got the. The directive on their desk from the mayor and the treasury of the mayor's office.

It says, you've got a million dollars. You've got a million euros, a million pounds, a million pesos, whatever. You've got a budget to promote this destination as somewhere that's attractive to digital nomads and remote workers. For you, Grayson, are there certain things that resonate with you and do you feel like there's anything that the cities or the destinations can do?

I. You're someone that's essentially voting with your spending, you will spend money somewhere. And we assume you're like, we know, we don't assume we know you're a great guy. You're not gonna cause trouble, you're gonna be a net positive and you're gonna spend money there. Is there anything they can do to attract you?

Or do you, do you get your information from peer to peer Reddit networks, other people? I'm just wondering. As these, I think there will be more and more destinations looking to capture the economic benefits of remote workers while also managing the perceived political negatives of gentrification and some of the backlash.

That's also part of their job, but they will be looking to attract the economic benefits of remote workers. Is there something they can do better or do. To attract you?

Grayson Harris: 100%. I would tell 'em to, look at, or maybe hire Gonzalo Hall. For people who don't know, he started the community.

Very specific,

Curtis Duggan: tactical, great advice. Yeah. Just hire Gonzalo

Grayson Harris: Hall. That's it. He started the community in Madea. I was actually just there right before Serbia and, for a digital nomad, one of the biggest things that. People are worried about, or it is being lonely and having an community.

Curtis Duggan: Were you in PON or CIA when

Grayson Harris: you were there? I sit in fia.

Curtis Duggan: Yeah. Yeah. That's a great city, isn't it? I was amazed by it. Sorry to just kinda got in tangent, but I think it's just an awesome city to, to highlight just for a second, just the way that it, it go. It's a Portuguese island closer to Africa and the Moroccan coast than it is probably to the Portuguese, the Iberian coast, and.

It really is, goes up this volcanic side of a mountain where the city just, I don't even know how to describe it. You can say something like Vancouver, Hong Kong, San Francisco in the way that they're vertical and have hills. But it almost doesn't convey it. It's like literally a city that just goes up the side of a volcano, I think, if I've got the geology right.

But anyway. Fun J's a great place. Sorry to interrupt your highlighting of how Gonzalo built community there, but I just, I love Madeira and wanted to highlight that.

Grayson Harris: Yeah, no worries. It's one of my favorite places and one of the great things is just the community that he's built there.

You can get there in day one, you can open up a Slack and for all these different communities around Madea, they post daily activities that you can go and instantly meet people. And so really getting, other tourist boards or other cities to. Not necessarily do the same thing I would love that.

But having some sense of community and that can be as simple as, having hotels build coworking spaces. It all starts with a coworking space. Like I said, if I don't see a coworking space in the city, I'm probably gonna go to a different one all the way up to, the model that Gonzalo is doing and Madea, or I went to his Village and people of Brazil where it's great for surfing.

And again, you kinda show up and there's instant access to all these other digitals in a community with that.

Curtis Duggan: Yeah and maybe just to even. Pump up Gonzalo even a little more. He, it started Madeira. That's the biggest one. But essentially he's created a model, and this is almost the, I don't wanna say the inverse or the flip side of the workation.

It's adjacent to the Workation. And I'm sure, of course, Gonzalo would argue, and I might even argue too, that this is in some ways. A superior experience or it's a definitely competitive experience to going on a workation. So if you think about a workation four weeks in Honduras, or four weeks in Croatia and maybe your, a complicated accommodation is taken care of.

It's still a commercial endeavor for the Workation operator to take whatever it is. Three grand of your money for an all like a quote unquote all inclusive month or a month where your accommodation and coworking is taken care of. You probably still have to pay for your food like on the vast majority of them.

But it's essentially we want to package up a new version of a tour for you. What Gonzalo is doing is, and I don't know, I think the model, the business model or the private public partnership model is different in each of the villages that he's done. And he's done them in Portugal and in Cabo Verge in an African island nation.

Off the coast of Africa, and also now in Brazil, in Pippa, in the Northeast. And I think that the model is different in each one. And so I don't wanna say it's a nonprofit. I don't know. I think it's a combination of things, but it is more. Expansive and it's that sense of just, I know and I know what you mean.

Landing in Madera and you open the Slack group and it's not like you're paying for a, an event or something or a tour. It's just a community you can join and it's more community driven in the words that he would use to be able to just say, Hey, there's some people doing this. There's some people doing that.

I'm not like on a group tour, I just. Show up somewhere, meeting other people and getting acclimatized to the locals and the community and everything that's going on really easily. So we'll see I, and we'll see what things can support that. I think Slack, as cliche as it is, simply just having a slack or a discord, as basic as that is, does change an entire experience of being somewhere for a month for a lot of people, especially when it's done well.

Like the Madera Nomads Slack, right? Yeah.

Grayson Harris: Talking about the loneliness it's a very easy thing to experience and I've definitely experienced in places. I would say if you're really worried about that, Madea, one of these communities is a great place to start out if you're feeling lonely in made.

It might be your fault. 'cause there's activities every single day. It's, go to one of those. And there's people just like you wanting to meet other people that are there.

Curtis Duggan: Yeah. Yeah. I agree. If you're feeling lonely, it's your fault. In Madera. In Madera, in, in this isn't the most important thing, but I do, for those that are.

Listening to this podcast have never heard of some of these places at all. There's a lot of stuff that's just like really quick to into people that have remote worked, certain places and names and things that are really familiar. Madeira might not be as familiar to people that have no connection to remote work or digital nomadism yet.

But if you imagine going to Lisbon, what is it? Is it like. Couple hours, an hour and a half to fly to FAU airport from the capital or the biggest city capital of the region, or county. I'm not sure what Madera is, but it is a specific kind of autonomous district. Getting a bit nerdy, but anyway, you fly from Lisbon to FAU and that's not very long of a flight, and it's usually a fairly inexpensive flight.

And then you have this island, which is not necessarily the same as. The Spanish islands that are fa, famous and familiar around it's not necessarily tons of sandy beaches, but it has a unique ecosystem and microclimate and biome that uniquely evolved because it is this island this volcanic island separated from the continent.

Then you got cia, the biggest city which is still a couple hundred thousand people, I think, and then towns and villages and beautiful nature all around the island as well. You know what you would do if you were sitting in Colorado, if you're in Boulder and you're like, I. I wanna do this.

What you just said, Madeira never heard that word before. Gonzalo. I'm gonna look him up. Digital Nomad community, I'm gonna go find out what that is. All you really have to do is probably get to J F K or get somewhere Atlanta, Dallas. You take a flight to Lisbon and then two hours later you're in this place off the coast of Northern Africa, Portuguese Island.

It's It's, I don't wanna make it trivial that it's not that hard, but it's not as far away as you think. Yeah. And it's easier to do than you think. And as, as you've mentioned, we've gone over, there's built-in activities and things to do right away. And yeah it's actually amazing.

It's not necessarily just some. I wanna pump it up. It's not just some lame bulletin board that says, we're having a startup pitch competition on Saturday, and then there's a morning run on Sunday, and then next weekend we're knitting. It's not like that. It's chock full jam packed of multiple daily activities.

I'm not paid to say this. They're not a sponsor of the show, but they really, they do. Many aspects of community really well. And I don't know how many analogs there are around the world. There are some nomad communities, but this particular way of doing it where it's been curated and built up like that.

Go m a d e i r A. If you wanna look it up, grace, and I know you're in Serbia and it's later for you. I wanna. As they say, be respectful of your time. I, I hope in the last 45 minutes we've been respectful of our listeners' time in the sense that, I don't hope, I know we have, we've hit on a lot of great points that I think can educate and inform people.

That's not necessarily that's not necessarily the point of the podcast just to educate and inform as David Brent from the UK office might say, bit of an entertainer myself. So hopefully it was I hope it was entertaining too. And yeah, it's been great talking to you and hopefully I'll see you, somewhere on the Nomad Trail before next running remote.

But I heard that it's in Lisbon again. It's been cycling through different cities Yes. Each year and then it was virtual during the pandemic. When, as in business and in life when something works, the best thing to do is maybe to do it over and over again. 'cause you start to get economies of scale and efficiencies and a community starting to build up.

So I am excited. That it is again, back in Lisbon in 2024 and I will be going, I'm

Grayson Harris: planning on going myself. We'll see exactly what happens, but definitely wanna say, appreciate, yeah, we won't

Curtis Duggan: hold you to it, but what there'll be virtual sessions and for anyone that wants to go, again, they're not sponsoring this, but I just, I think it is an interesting community that pops up around that event every couple days, every year.

Yeah. Any other things that besides running remote that you're going to as an event or a planned visit? Nomad Fest or, Bulgaria, there's various other places. I haven't done many of those, so that's the only reason I ask.

Grayson Harris: Running remote was really my first one of those, and I wasn't planning on it, but last minute.

I am going to sco nomad fast here in a few weeks

Curtis Duggan: in area. Nice. Yeah, I haven't been I'm jealous. I don't think I'll be able to make it. It's a little far from where I am, but yeah. If you're in Serbia, it's not so bad and I've heard great things about it. Yeah. I'll have to,

Grayson Harris: I'll have to

Curtis Duggan: tell you all about it.

Alright, Grayson. Have a good night and thanks for coming on the Remotely Serious podcast and enjoy Serbia.

Grayson Harris: Awesome, thanks.