How to be a Digital Nomad

by Will Francis

Posted on May 3, 2024

Travel the world in this week's episode! Host ⁠Will Francis⁠⁠ peeks into the digital nomad life, chatting with Chris Cerra and Michelle Coulson. Chris founded the platform ⁠RemoteBase⁠⁠ for finding remote accommodation and Michelle built HR platform ⁠Remote Rebellion⁠ out of frustration with companies calling people back to the office.

They have tips for newbies, choosing the right destinations, essential gear, and the challenges and rewards of remote work. We also get some insights from Chris on his remarkably successful email newsletter and MIchelle's approach to LinkedIn.

Top Tips for Digital Nomads
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Podcast Transcript

Will (00:00)
Welcome to Ahead of the Game, a podcast brought to you by the Digital Marketing Institute. I'm your host, Will Francis, and today I'll be talking to two digital nomads who've built their lives around remote working whilst helping others to achieve their dream of living and working around the world. Michelle Coulson established Remote Rebellion out of frustration with companies calling people back to the office post -pandemic.

She's worked as a recruiter and headhunter at global consultancies and digital agencies around the world. And now Remote Rebellion helps people secure well -paid remote work which aligns with their values. Chris Cera started his nomadic working life in 2018 and now runs Remote Base, a newsletter and community that helps digital nomads find places to work and stay. This year, he launched which invites nomads to submit their reports of great remote working spots from Medellin to Madeira.

Guys, welcome to the podcast. How you doing?

Michelle- Remote Rebellion (00:55)
Hello! Thanks for having us.

Chirs @ RemoteBase (00:56)
Great to be here, thanks.

Will (00:56)
Oh, it's great to have you. Oh, it's really good to have you. We've been meaning to talk about this for ages, you know, this idea of nomadic living and working. So I'm going to mine you for all that you know and all that you've experienced over the last few years about that. But firstly, just give me a bit of background. Why did you adopt this way of life, Michelle?

Michelle- Remote Rebellion (01:24)
Mine has a really long story that could be here for a few hours on, so I'll try and give you the shorter version. I was actually talking to my mum and sister about this the other day. I've not lived in the same house for longer than two years since age 11, so I think the nomadic side of me was born maybe back when I was 11. We moved to Spain and then moved around a lot. And I think that's where the seed was planted. However, as with everyone, you have to, in your...

mid late 20s you have to do all of the things you have to buy a house and you have to get a good job and you have to stay where you are and do all of the things you should do at that age, until the pandemic came and I was like I'm really unhappy. I'm in London I'm in this small flat I'm working hard and it really gave me some time to stop and think that I was just keeping myself busy as people do in London going to the pub going to the theatre doing all of these things and I realized what makes me happier is being by the sea.

So it was March 2020, we couldn't move anywhere. And I started thinking about what that looked like as soon as I could move. So working in recruitment, I had been pushing for a remote work policy at the company I worked for for ages. And I managed to get hybrid, so four days a week remote, but that still meant I was restricted to having to go to the office every Friday or whatever that was. And I love the office environment, but I just felt really like stuck, like I had to go there. So.

With all of the offices pretty much being locked down, I said to my boss, hey, we're working remotely right now. I got an invite to Bali. I thought I'll go there until the office opens up again and I'll make the most of those couple of months. So I did, went to Bali, was working for this organization and I loved it. I was so happy. I was surfing every day. I was doing my work. I was meeting people that were like -minded and I was the happiest I'd ever been.

And so when my boss actually called and said, right, Michelle, back to the office now. The London office is opening. I was like, hell no. Like there's no way I'm going back. And I said, why can't I continue to work remotely from here? And he's like, computer says no. A bit of a Little Britain reference for those people who know, but it was a no and there was no good reason for it. It was a case of, well, this is company policy. You have to come back. I was like, that's not a good enough reason. Give me a reason why like my work is better over there. So he said no again. So I was like, okay, I quit then.

and didn't have savings, I had a mortgage to pay, didn't have anything to go to, but I just knew that there wasn't another way for me. It wasn't necessarily about being nomadic, it was about having the freedom to choose where I work from. So Remote Rebellion was born. I was looking for a remote job for a while, I really struggled. I realized how much more difficult it was to get remote work and I'd been in recruitment for 10 years and I was still struggling. I had a good network, 2021 was a really good time for recruiters to get work as well and I still struggled.

Will (04:17)

Michelle- Remote Rebellion (04:19)
So I was like, wow, if I'm struggling this hard, other people are gonna struggle. So that's where remote rebellion was born. And I guess that's where this mind opening of you don't have to be in one place, you can work from anywhere. That's where it was born.

Will (04:31)
Great. What about you, Chris? How did you become a digital nomad?

Chirs @ RemoteBase (04:38)
Well, my journey was a little bit different. And it's really interesting to, it's super interesting actually to hear that from Michelle because Michelle and I have met at various events in the space around the world over the last maybe year or so. But we've never had that conversation. And so it's, well, maybe not to that level, not like not.

Michelle- Remote Rebellion (04:54)
Have we not?

Chirs @ RemoteBase (05:00)
I guess like parts of that have come out in conversation, but I've never heard like that answer in, you know, in that sequence before. So it's super interesting to hear it in full. I'm like the total opposite of like a third culture kid. I like grew up in one place for my entire life. I stayed in the same house until I was 18, but always loved traveling. And my dad used to work in travel. So I think part of me was, part of me was...

yearning for travel for a long time. And back in 2016, I was really fortunate. I got a job that was remote friendly. And this was a time, this was like before remote work was a buzzword. But in 2016, it was an introduction for me to working remotely at a time when I was like early to mid 20s. And I was doing all of those things that Michelle talks about, right? Like,

this is the, these are the steps that you must follow. Like these are the instructions for life. And somebody planting the seed and saying, oh, at this company, we have a policy where you can work from anywhere as long as you get your stuff done. For me, that was a bit of a epiphany moment where I realized, oh, there's, there's another way to look at this, which is outside of this tribe that I was previously in, which is like, this is your instruction manual, off you go. And that was,

that kind of snowballed for me. So introduction to remote work in 2016.

By 2017, I was regularly working remotely domestically, whether that was from London, where the office was, or from around the UK with friends and family. And by 2018, I was like full -time international nomad. I'd left London and had gone hard into digital nomad life and that  So my background was always in marketing.

Will (06:55)
And what kind of work was it?

Chirs @ RemoteBase (07:04)
That was what I studied and I worked in various startups, but that role was, it was actually in financial services, which is on paper, one of the most buttoned up industries. You know, you think financial services, London, you think, no way is this gonna be a remote opportunity or a remote friendly opportunity, but the company was very progressive. The organizational structure was very flexible.

And yeah, I think to be honest, on reflection, I think it would be considered progressive even in today's world. But back in 2016, it was almost unheard of. And so, yeah, it was a very fortunate opportunity for me. And I often look back on at that time and think how much different things would be if that opportunity hadn't come about when it did.

Michelle- Remote Rebellion (07:55)

Will (07:56)
Yeah, absolutely. It's interesting. I mean, I suppose the logical next question is to ask you about the pros and cons of it, you know, because I similar thing, I've moved to Ireland in 2017 and went remote and before the pandemic and then was really set up for that. And so I get all the benefits of that. What are the  downsides of working remotely? You know, do you think that you've had to make any sacrifices, Michelle?

Michelle- Remote Rebellion (08:24)
It depends whether you're asking the downsides to working remotely or the downsides to being a digital nomad, because I think they're different. They're not necessarily the same. So which ones do you want to focus on?

Will (08:31)

Er, well give me a couple of working remotely first.

Michelle- Remote Rebellion (08:41)
You've got to manage your own time better. And it's hard for me to say, managing the time zone, having more flexibility in your schedule, which generally comes with remote work, not always, can be a blessing and a curse. I love flexibility, but I'm also like trying, I'm constantly calendar managing. So I'm like, okay, I wanna have coffee with my sister. So if I just move this meeting here and I do this here and then I do, you're trying to cram so much in cause you wanna live life, which is a great thing.

but it can come with its own challenges. And often actually being in this bubble as well, you forget other people don't have that. So you're like, hey, do you want to go to the water park on Wednesday afternoon? They're like, 2 p .m. on a Wednesday? No, I'm working nine to five. And I'm like, oh, people live that life. So that can be a downside sometimes. But I guess the things I'm talking about are not necessarily remote work specific again, like being your own boss and managing your own hours. They're kind of the challenges that come with that. And...

Will (09:23)
That's so funny.

Michelle- Remote Rebellion (09:38)
having like the amount of times I've had people being like, oh, you're working on a Sunday. I'm like, do I have to go and explain? Yes, I'm working on a Sunday so I can go to the water park on Wednesday afternoon. You know, like you feel like you're explaining these scenarios. So when you're in the world of other digital nomads and other remote workers, they get it, but then coming back home to Manchester and being with people like, you feel like you have to explain it because it's not understood. And then there's the typical.

wifi issues, connection issues, background noise, those kind of things can happen sometimes.

Will (10:12)
Yeah. I mean, you're right. To me, do you know what I've thought over my time working remotely is that I think there's certain personality types. Like personally, I love my own company and I love having that freedom to, you know, the things that people talk about being stressful aren't stressful to me. I like being on my own and I like dealing with my own time and being able to, you know, have that freedom. Some people really need, I think, the...

the box of nine till five to work with and then they know that after five o 'clock they're free and they've been given that license to do what they want without having to make that decision themselves.

Michelle- Remote Rebellion (10:54)
Yeah, and I used to be so anti 9 to 5, you know, I used to be like, don't work a 9 to 5, and I actually see there is freedom in that, you're right, and it's a personal preference. I personally wouldn't be able to do that because anyone who tells me what to do, I want to do the opposite, even if I want to work a 9 to 5. But I do think there is freedom in actually having that structure, and some people do need that and work better in that way as well.

Will (11:16)
Yeah, absolutely. What about you, Chris? What sort of hurdles or friction have you encountered with this lifestyle?

Chirs @ RemoteBase (11:28)
Michelle touches on something which is key, which is the differentiation between remote and nomad life. And I'd actually, I'd go as far as cutting further over into remote work in terms of flexibility, because a lot of companies offer flexible working and that by itself offers a whole realm of challenges around like discipline, like remote or not. But I think...

I think you've covered remote work challenges fairly well. I think the thing I'd add about digital nomad life is that if you're doing digital nomad life, there is a high risk that it turns into another part -time job on top of your current job, by organizing all of the travel visas, even things like...

Will (12:14)

Chirs @ RemoteBase (12:18)
You know, you fly into one place, but you're staying three hours away. You have to organize a transfer in a language you don't understand. Maybe you're jet lagged. Like that, all of that stuff, planning it out can be, can be stressful. And one way that I like to describe it is kind of like a, it's a muscle that you build over time. Um, so people always ask me for tips or they ask me like, Hey, how can I do this? Or how do you do what you do? And I realize that the first time you do it,

try not like no one walks into the gym and picks up the heaviest weights they can find like that that would be stupid and and some some do try

Michelle- Remote Rebellion (12:52)
some try.

Will (12:58)
kinds of job, I don't know if this is just a really daft question, but what kind of jobs can you and can't you do broadly speaking? Is it just, is it all very obvious kind of knowledge work that you can do nomadically or are there other less obvious kinds of work that you can do? Michelle.

Michelle- Remote Rebellion (13:16)
There's all sorts. I'm actually working with a nurse at the moment. So people think there's certain roles that can't be done remotely. And even if you haven't done the jobs that you think you can do remotely, there will be expertise, skills, experience that you have in what you've done as an on -site job that you can transfer over to remote. So I've worked with a kitchen fitter. He fitted kitchens for a living. Chris, you met him, right? So he went into SEO and content writing.

Will (13:21)
Wow. Okay.


Michelle- Remote Rebellion (13:46)
because he had an interest in something else. He didn't have experience in it. He just had the, I guess the time and the energy to put research into something and to figure out what they wanted to do. I was working with a dance choreographer on cruise ships who moved into HR because she realized a lot of the things she was doing with the teams that she was working with, she was kind of doing it unofficially. So it does, you can pretty much.

do anything within reason. There's obviously certain jobs that you can't do remotely, but even if you haven't done it before, it doesn't mean that you can't go into doing it. And a lot of people say, well, I can't do that because - inserts reason - I don't have a degree, I don't have experience, I'm too old, I'm too young. I hear all of them. The key to success to working remotely and getting a remote job, experience or not, is actually the right attitude and thinking, right, well, I don't know how to do that. How am I gonna get into it?

And I'm not saying it's easy, living a digital nomad life is not easy, I never pretend it is. But if you want it enough, then you will make sacrifices and you'll work hard to get there because the remote job market is hard right now, it's competitive. So you have to work harder than you would have to two years ago when it was a bit easier to apply for jobs.

Will (14:52)

Yeah, it's not like everyone has to try and find a way to work in marketing or something that's very obviously remote, right? Like you say, it's take what you know, what you've got as skills and adapt it. It's a good point.

Michelle- Remote Rebellion (15:10)
And maybe not even skills, it could be industry experience. So you get a lot of people, a lot of health tech companies wanna hire ex doctors, nurses, or people who work in on-site jobs. So they've got that knowledge of the industry, not necessarily the role that they're gonna do, but they want that knowledge.

Will (15:13)

Will (15:26)
wannabe newbie nomads ask you for a few tips, what do you tell them, Chris?

Chris Cerra (15:33)
Well, I think there's a definite efficiency to be found in staying in places for a longer period. So you're not going to get burnt out and usually it's a bit cheaper. You can get all of the best accommodation deals if you stay for a month or longer, which is my specialty, I guess. But for just getting started, especially for people who are concerned or have...

worries about what this might be like and whether or not it's right for them. I would say go to somewhere that you're familiar with and try not to bite off more than you can chew. Go for an extended weekend. So maybe fly somewhere on a Tuesday, work Wednesday, Thursday, Friday, maybe take Friday off, and then fly back on the Sunday. And then build up from there, you know? Like I said, it's like a muscle. You've got to train it. You've got to train yourself.

Will (16:22)
Yeah, and what's my checklist? So I need my, you know, obviously I need my gear, most of my computer and phone and stuff, a good setup maybe for Zoom calls. I need an Airbnb. Like what other things do you check about where you're going before you go?

Chris Cerra (16:39)
So something that's become really important for me over the years is space. Michelle touched on the fact earlier that I'm traveling with my partner. So she also obviously works remotely. And so for us, having space in a place is really key. A lot of the time, we'll book a two -bedroomed Airbnb just because it gives us like an extra room for something like calls, or we also like to invite people out to visit us, and that can be useful for that.

Will (16:44)

Chris Cerra (17:08)
but primarily for the desk space. And yeah, in terms of kit, like all of the things that you would need to do your job if you were doing it in the office. But if you're doing Zoom calls, then grab a little mic like this. Headphones are usually okay. Like standard headphones will do most of what you need them to do now. And yeah, apart from that, there's some stuff that I use, which is maybe a bit more personal preference, like I have this laptop stand, which is height adjustable, and that helps me

not have horrible back pain if I'm working in a place where the desk is too low or too high or whatever. And yeah, outside of that, I think there's little kind of software tips that you pick up. Like I have my calendar always set in two time zones. So I can always see.

like what my family time zone is and stuff like that. Or if you work with a team that's all located in one place, use your calendar to always like show both times on your calendar because time zones can cause a lot of headaches. And the worst thing you can do is, especially if it's your first foray, the worst thing you can do is have some kind of blip with time zones and...

Will (18:15)

Chris Cerra (18:21)
If you fumble on that, then your team will start to wonder if this is like a way that's sustainable for you to work. So try and keep on top of that.

Will (18:28)
Absolutely. It'd be basically you'll prove to them that it doesn't work and you don't want to do that. That's good tips. Yeah. Yeah. There's so much gear again, because of the pandemic, there's so much gear you can get now, like good cheap microphones, ring lights, better webcams, if you need that. Me and my wife, I guess remote work and she has this thing that's like, she's a designer and she has a second monitor, really big second monitor. That's just like, basically like, it's like a big iPad. It's just a thin monitor you can plug into your laptop.

Chris Cerra (18:55)

Will (18:58)
There's loads of ways that you can actually reconstruct a proper desk experience out of a suitcase. Oh yeah.

Chris Cerra (19:02)
Yeah, I use one of those too actually, like a travel second screen.

Michelle Coulson (19:05)
Yeah, me too. Is it the espresso one? I love it. I mean, it's great.

Chris Cerra (19:10)
 I'm not being paid to promote any brands so I'm not talking about brands. Yeah, espresso is really good.

Michelle Coulson (19:14)
No meaning if I like this one.

Will (19:18)
Yeah. Cool. Alright. Yeah, cool. What about yourself, Michelle? What sort of things do you tell newbies as a bit of a few nuggets of advice?

Michelle Coulson (19:29)
Not to overthink it, I think people generally find a lot of barriers to starting. And yes, I got a second monitor, I got a keyboard, I got a proper mic, I've got all of this, but you don't need that to get started. You'll start to realize the things that are gonna be additionally helpful for you, but you really don't need it to get started. You need a decent laptop that's quick enough and has good wifi. You need a backup mobile data.

and a global SIM would be useful as well. They're the real bare essential. For me, a bare essential, these headphones, like they go everywhere with me. They're all tattered now from two years of being like used up pretty much on a daily basis. But these are not just good because they cancel out noise in the background. But I did a call from a pub quiz in the back room of a pub quiz and no one heard what was going on around me. So like, like they're good in cancelling out the noise. Cause that can be super irritating. I'm quite sensitive to sound. And if I'm on a call with someone I can hear like.

a lot of background noise, it's really irritating. I can't really focus on what they're saying. So being considerate to not just what like distracts you, but what can be a bad experience if you're interviewing or if you're working with colleagues, it's just a reason to be like, oh God, if he was in the office, you know, that it'd be so much easier. But so just any reason that people can find who don't believe in remote work, they'll find to highlight why this is not suitable. The same with, yeah. Yeah, exactly.

Will (20:42)

Yeah, you want to be the dream Zoom meeting attendee basically, right?

Chris Cerra (20:53)

Michelle Coulson (20:55)
So things like overestimating how long travel is gonna take. If you've got a travel day and you say you land midday and you're like, oh, I can get a call in for 3 p .m. Don't, if you can try and write off that day as your travel day and book in any calls or things that you need to do for other days, you'll thank, because I'm always optimistic. I'm like, yeah, I've got plenty of time for that. And then I'm rushing around, I'm stressing. So block out a travel day. That would be my biggest advice.

Will (21:23)
Yeah, yeah, I really agree with that as well. I think we're all a bit optimistic with time and you end up taking the call on a bus or something. Okay, cool. Well, you know, you've been to lots of places. How many countries have you visited and worked in at this point, Michelle?

Michelle Coulson (21:28)
I'm out.


Over 60 countries visited. I have not done a count for a few years, so I'll have to do an update on that. And worked in probably six, seven different countries over the last few years.

Will (21:54)
And which countries are they? Just give us a shape of where you're spending most of your time.

Michelle Coulson (22:00)
Thailand, so I generally mix between Thailand, Indonesia. I absolutely love being in Bali, being in Thailand, I love Southeast Asia, and anywhere between UK, Portugal, Spain on the European side. So they're kind of my main bases, and I'd say where I spent most of my time working.

Will (22:20)
Nice. And are they... Do you find that kind of digital nomad culture kind of clusters around certain hot spots in the world?

Michelle Coulson (22:29)
Yes, they do, but you can find some hidden, so like Chris at the minute is in Albania, that's a really interesting one. It's becoming more popular. So Bali is very much a big hub for digital nomads, but it's becoming a little bit saturated because of that. But there's a reason that people go to these places. So you can say, I'm gonna go where it's a bit safer, where I know there's gonna be reliable wifi, there's gonna be a community of nomads, or you can branch out, do a little bit of research first, what's the wifi gonna be like? And...

Will (22:36)
Hmm, third.

Michelle Coulson (22:55)
Again, I wouldn't overthink it. You don't have to have everything lined up and everything researched before you just need to give yourself a bit of leeway So I kind of I kind of wish that I had done a bit more research in the island that I went to in Thailand. I went to a really small island, I'm not going to talk about it because I don't want it to get overrun, but the wifi was terrible So I was there for a month and I didn't get a sim before I went to use off my data so I ended up paying quite a lot for my mobile data and

Will (23:19)

Michelle Coulson (23:22)
But I'm really glad that I actually didn't do the research because if I had, I probably wouldn't have gone and I had the best month of like in a long time. So sometimes it does better to just make it work.

Will (23:32)
Yeah, I get that. What about yourself, Chris? Have you worked from a lot of different countries?

Chris Cerra (23:39)
I think so. I don't think I've been to more places than Michelle. I think I'm probably, countries I've visited is probably only in the region of about 30, which is for people who count countries, that's maybe not a lot. But I...

Michelle Coulson (23:44)
not a composition.

Chris Cerra (23:57)
I often find that we cycle back to the places that we really like. So it's not the part that typically I'm seeing that I visit like between 10 and 12 countries a year. Often I'm staying for two or three months, but I'm taking like a short day trip or a short visit for a weekend, like getaway to a new place. And that's allowing me to explore that. So.

A great example is like last year I was here in Albania in a different city, but from there I could take a day trip into Montenegro. You can take a day trip into Kosovo. You can do these day trips which are, or short weekend trips. You know, you go to Bosnia for a weekend, amazing. But countries to kind of be situated in and work in over the course of the year, if you're doing two or three months, it's only...

three, four, maybe five countries and...

Yeah, cycling back to those places that I know I enjoy and I know I can be productive in is a great way for me to keep my environment fresh and keep productive, but still explore. And I often find that the cycle basically evolves. So you go to Bosnia for a weekend and you think, oh, this is great. Maybe this is a place that I could get set up here and I could work here for a month. And then when you go back, that's what you do. And then that then brings itself into the cycle and you slowly move around the world.

Will (25:14)

Chris Cerra (25:23)
to get into know places a little bit closer that way.

Michelle Coulson (25:26)
was going to say it's definitely changed for me. Like I'd say the majority of those countries I mentioned have been in my 20s, in my 30s. It's been, I've much more, I've craved the base and not felt the need to have two weeks here and one week there, which I did in my 20s, because you want to see as much as you can. But I think you're right in terms of cycling back, like, well, I like Portugal, but I haven't been to this part of Portugal, so I'm going to go here or like exploring more within your own country as well. Like I'm...

Chris Cerra (25:49)
Mm -hmm. Yeah.

Michelle Coulson (25:52)
going to camp around through the UK for a month. So I'm actually seeing places I haven't seen before. So you definitely travel. I think it is an age thing as well, but actually needing a bit more stability in your setup makes a difference.

Chris Cerra (26:03)

Will (26:05)
Yeah, it's true that. I think we're all a bit like that on some level. And Chris, what's the sort of, what are your hotspots? What are your kind of, which countries do you mainly spend time in? Just out of interest.

Chris Cerra (26:15)
So again, I'm also a big fan of Southeast Asia. So we typically will spend like the back portion of the year in Southeast Asia from kind of September into into new year. The obvious reason is like you avoid the winter, but it's a really fun place to be. And there is, we talked about like the hotspots, right? Bali is a big one.

Will (26:34)

Chris Cerra (26:42)
I am a big proponent of Chiang Mai in Northern Thailand. So we're often there, but there's other places like Vietnam, which are gaining in popularity, Malaysia gaining in popularity. And then in Europe, I am a big fan of Portugal and Spain, but also like I've spent the past few years exploring the Balkan region. I'm here in Albania. This is a place that I've returned to. Last year, it was for one month. This year it's for two months. That's probably going to evolve.

like this place is probably going to evolve and I've seen in that time, spending three months in a country you can see so much of it. It's not a huge country, so it's quite easy to see a lot of it. And yeah, it feels really good to almost touch the culture here, which you can't do in a weekend.

Will (27:28)
That's great. No, you can't. And I'm interested, you know, you you go to these places that maybe don't have so much tourism. How do the locals respond to digital nomads? How's that? How do you kind of like, how are you received there, Chris?

Chris Cerra (27:47)
Every place is different. Every place is different, but I mean, I'll talk about Albania because I'm here now. So many people have recognized us because we're in the local area and we're visiting the same coffee shops or restaurants, cafes, whatever. So many people after so long will say like, are you living here? Because they know that we're not from here, right? We don't speak shqip, we don't speak the Albanian language. And...

Yeah, it's like, it's kind of nice. It's nice to be recognized in a place. And, you know, there's places now where if I go and do some work in a cafe in the morning, there's places where I can walk in, wave hello, and my coffee is brought to me without me even needing to order. And we have a conversation with the staff and like they recommend other places to go and things to do. And it's nice. It's kind of...

Will (28:37)

Chris Cerra (28:41)
It makes my heart glow. It makes you feel warm inside that there's somebody in the place who is happy to have you there and is willing to engage and is curious to learn more. They're like, do you work here? Like, oh, you work online. What do you do? I'd love to do that. Or like, yeah, it's special. It feels really special and it's different in every place. That's probably the takeaway there.

Will (28:43)

It is. What about you, Michelle? How have you found your lifestyle received and the curiosity or the reaction to that in different places?

Michelle Coulson (29:16)
I think in most places I've experienced it's been curiosity has been the main thing I've come across, which I really like. And I think what I like most is what annoys me is when people, when you tell people about your lifestyle, whether they're people from home or whether people you meet, and they say, oh, I wish I could do that. That kind of like, in most cases annoys me. And I'm like, well, you can, but I really love it when people are really honest and they're like, oh, that sounds great, but yeah, that's not for me. I like my home comfort, so I like this. I'm like.

Will (29:24)

Michelle Coulson (29:46)
I really appreciate when people are honest like that, because it's not for everyone. So I think the people who are intrigued by what you do, but they're like, you know what, that's not for me. I'm like, great. It's the people that I wish I could do that. You can, like you can do it. That's the main thing. Whether you've got kids in school, whether you feel like you're too old to do this. Like in most cases, there's an option for you to do it. But I haven't felt any animosity.

anywhere I've been, touch wood, I haven't felt that. I've heard about it in places in Portugal. I've heard about people graffitiing, oh, in Mexico, people graffitiing, nomads go home, you're putting the prices up for us locals.

Will (30:28)
Because that's the thing, isn't it? It's the rentals, the short -term rentals, I suppose, is the bit that people get annoyed about in some places.

Michelle Coulson (30:34)
But people love a reason to blame other people. It's like you get in certain parts of the world, like foreigners are the issue, are the reason for issues in their country. It's so easy to push the blame onto someone else. So I don't think that's specific to nomads. I think people just like to find a scapegoat and a reason for any kind of issues within their government or within their country.

Will (30:58)
Yes, true. I mean, if there weren't people who owned properties putting those properties on Airbnb, then you wouldn't be there. So, yeah, that's a good point. Well, that's good. That's all really interesting to hear, actually. We'll be putting together some checklists that people can download around this kind of stuff for listeners, by the way. Okay, cool. You know, to you again, Michelle, I'm interested in, you know, you talk about helping people secure highly paid work.

Michelle Coulson (31:03)

Will (31:28)
How does career progression work as a digital nomad? Are you in any way held back or... I suppose that's the wrong question because I know you're going to say no but is there must be certain types of friction in terms of career progression to those more senior roles do you think?

Michelle Coulson (31:45)
There is if you are working for a non remote-first organization. And I think that's the difference. If you're going into a really large multinational and you're kind of maybe one of the exceptions, other people are working on site and they've typically been on site for most of the organization's career, then yeah, I think it's naive to say that people who, you know, John and Bob are meeting at the water cooler and they've got this relationship because they go to the pub together, that there's going to be that kind of relationship formed on site that happens.

However, the majority of what I'm teaching people is rather than trying to be the exception, going for organizations that don't just accept remote work, but they believe that it is a better way to do things and everyone is working in that way. It makes no difference whether you're remote or not, as to whether you wanna get that promotion or you wanna progress. And another thing is you don't have to have a career, you don't have to progress. If you just want a job that pays your bill so you can have your lifestyle,

What's wrong with that as well? Like it doesn't have to be this progression that people are going up. Some people have taken a pay cut and have taken a drop in responsibilities because they want less stress. I'm not saying you have to do that if you want to work remotely, but so what? Like, does it really matter?

Will (33:03)
Yeah, it's true. It's part of a bigger life choice, isn't it, that you make around, like you say, maybe less stress and better work -life balance, et cetera. I get that. But okay, and just when people ask you, okay, so I wanna earn as much money as possible working nomadically, what do you say? I mean, are there certain types of roles, certain types of industry that you sort of point people towards?

Michelle Coulson (33:33)
I'd ask them why they want to earn that money first. What do you want to spend the money on? What is really important to you? I had one guy I was speaking to once and I remember asking him what his interests were. Why do you want to work remotely? What do you want to do? What are you passionate about? And he went blank. And I just remember how sad this was. And I remember seeing a guitar in the background and I'm like, do you want to play guitar? And he's like, oh yeah. And he'd forgotten what he was interested in. And he was like, but I want to earn the same money because I'm earning this money now and I want to continue earning that money.

Why though? What do you want with this money? And I know it sounds like a really cheesy to talk about it rather than what you're earning, but what are you earning the money for? What is the reason for that? For stability, for a bigger house, for a bigger car, for your kids to go to a fancy school, what are you actually earning that money for? So yes, I help people to secure well -paid work, because I say you don't have to take a pay cut to get a remote job, but that's not the be all and end all. And it's working out what ideal looks like for them.

And that could be the ideal is 100K a year, whatever that is, but they're happy to work weekends. And then what they're like happy to accept is, and also what their non -negotiables are. Those are the three tiers of figuring out anything before going into just an arbitrary number. Well, I've been earning 100K, so I should continue to earn 100K. Why? Why is that important?

Will (34:55)

Good way to think about it, that. I like that.

Chris, I want to talk to you about the fact that you've actually built, you've both built personal brands and you've shared your story, your expertise, your experience in different ways. Chris, you've done that through an email newsletter that I mentioned in your intro.

Talk to me about why you chose email rather than sharing what you do on TikTok or somewhere else. Why that channel?

Chris Cerra (35:30)
Very interesting. When, fundamentally when I had the idea for this, I was, it was around about the time when email newsletters were becoming really popular as businesses. So there were, there were companies running standalone email newsletters as a business. The really, really big ones out there now are things like Morning Brew or The Hustle, which was acquired by HubSpot like,

really, really serious email newsletters, like publishing every day, millions of readers. It was a big deal. Yeah, yeah, they're essentially like media outlets. They're huge. They're not just an email. And at the same time, I was taking a little bit of inspiration from a company, an email newsletter organization in the UK called Jack's Flight Club. Now there's...

Will (36:07)
And they're like publishers, aren't they? That's a good word, yeah.

Chris Cerra (36:29)
versions of this around the world, like in the US they have Dollar Flight Club or Matt's Cheap Flights or Scott's Cheap Flights and they're essentially like flight hacking.

alerts. So, you know, when the price of a flight dips, they'll get, they'll email everybody and let them know. And I was looking at it from the perspective of why can this not exist for long -term accommodation deals for digital nomads? Because people were doing it for flights, some people were doing it for holidays, but there wasn't really something that was specific for digital nomads. So that was the first thing.

And I thought about other channels. I thought about Facebook groups and, you know, there's a plethora, right? Like I could just run this as a run this, like you said, as a TikTok account. But I know people who don't have a TikTok account and I know a different group of people who don't use Instagram and a different group of people who don't use Facebook. But Will, let me ask you a question. Do you know a single person who doesn't have an email address?

Will (37:34)
I do not know a single person though.

Chris Cerra (37:36)
So for me, for me it was that it was about distribution and it was about it was about being able to guarantee access and own the audience and not rely on the other people's algorithms to to get in front of people And that was kind of it that from that point things progressed from there and that was why I chose the channel I chose

Will (37:49)

Right, and how did you grow it? Have you got any tips for email growth?

Chris Cerra (38:03)
Yeah, this is an interesting question. The newsletters are around 5k subscribers. So you look at that against the backdrop of Instagram influencers or people on YouTube with like hundreds of thousands or millions of followers. And it's a fraction of that. And that's absolutely OK because I own the audience. And so in terms of growth, I think...

you have to look at newsletters as like a two -part process. One is content and the other one is distribution. And if you nail the content, brands often are poorer with the content side, but they're really good with distribution because they're selling a product or they're selling a service and they're collecting an email. So the distribution is covered, but maybe they suck at the content. The flip side of that is if you're a personal brand or just a standalone newsletter business, you probably have really, really good content

but your distribution probably sucks. And the way to fix that, it varies based on the size of your audience. If you're like zero to a thousand subscribers, I think you just have to get your hands dirty a bit and be in the forums, be in places. Like I often use this example of like a newsletter about knitting where...

sometimes you have to go really really unscalable and you have to go offline. It's like if you're running if you if I wanted to start a newsletter about knitting tomorrow, I would go to every knitting club in my area or every like weekly knitting night  and share it Exactly. Exactly

Will (39:33)

You have to really show up in your niche, don't you? I've seen a lot of that in that world, yeah.

Chris Cerra (39:41)
And as it scales, the tactics change. So once you get to 1,000 and you go from maybe like 1,000 to 5,000 people, it's gonna be a little bit different. It's not gonna be so unscalable. At that point, you can start to use more organic content. You can introduce referral systems, partnerships, stuff like that, and cross collaborate. And if you show up with a personality, that will become its own growth system. If you...

Will (40:10)

Chris Cerra (40:10)
build a good foundation of readership, that will become its own growth system. And you can leverage that with things like referral systems. And once you get past that in length like 5K plus, then you can start to do the more traditional tactics with like paid growth. And then as you get to like 10K and above, that's when you can really start to deploy super scalable tactics like acquiring other digital assets or go really long on brand partnerships and other distribution channels.

Will (40:40)
Yeah, nice. That's a really...

Chris Cerra (40:40)
So it depends. It depends where you are and where you're starting your growth from.

Will (40:45)
Yeah, that's a really nice run down of that. And Michelle, you've grown your personal brand on LinkedIn. That's where you've kind of focused your time, right? What have you learned whilst doing that?

Michelle Coulson (41:01)
What have I learned whilst doing that? Quite a lot, but I would say that, again, it's not overthinking it. I think people are like, oh, I need to think of content every day. I need to do this, I need to do that. And so many of these shoulds. And I think being authentic and posting about what you believe in and what your audience wants to see is the focus on this and being consistent with it.

To grow an audience, you need to be consistent at posting several times a week. So actually, rather than just going into bursts of it, planning out and scheduling your content where possible, but leaving some room for sporadic things that pop up. Like I get ideas often, and generally when I'm on boats or bikes, I usually say this. So it can be really annoying when I'm cycling and I'll be especially going up a hill and I've got an idea and I wanna write it down. I'll have to stop at the side of the road, and write it down. So you don't.

I think if you sit down, I would never have said I was a creative, which is, I've been saying that to myself for years, but I have these ideas all the time. So maybe I am creative, but they just pop up in really inconvenient times. So actually being able to write them down and then when I have time, bulking them out later and talking about that as well. And just experimenting, being comfortable with

your post not getting the traction that you hoped it would. I did a meme the other day and I was really proud of it. It was like a skydiving meme, someone with a beautiful skydiving photo. Did you see this, Chris? It's a beautiful skydiving photo of someone else and then me with my absolutely  my cheeks like this. It was awful. So I was like, how your remote job search was supposed to go and how it really went. I thought it was really funny. I was like, this is gonna go viral. This is gonna be like, people are gonna really find this funny.

Will (42:43)

Michelle Coulson (42:45)
and it didn't get the traction I hoped it would. So something that's funny and entertaining to you is maybe not someone else. And then you'll do a post about something and then it will get loads of traction. And I hear this from people who have been content creators for years and they say the same, like sometimes it's a bit of luck, sometimes you don't know. So being okay with something flopping and actually analyzing the posts that do well and doing a little bit more like that. So just, just trial and error and not having...

Will (42:55)

Michelle Coulson (43:14)
the followers as vanity metrics. I think you can become so obsessed with, I've got this many followers and I got this many likes. It doesn't really matter if they're not converting into the customers that you're looking for or you're sending the right message. Just to do something just for the sake of being controversial or just to get loads of followers, it doesn't sit well with me. So I think doing it authentically and that

Will (43:18)

Michelle Coulson (43:37)
 will come across. I've had a few people comment saying, oh, I just, I like your posts, they're entertaining or they're authentic. And that means a lot to me when people say that they're like, okay, good, that's me coming across, that's my real voice. It's not just doing something to get the likes.

Will (43:41)

Yeah, good. It's a really good point about persistence for sure. I mean, the way I see it, the list of successful creators in any realm, whether that's online, social media creators, writers, authors, musicians, that list is literally just the list of people who didn't give up. Right? And so, yeah, I mean, so, I mean, so demoralizing, isn't it? Because it's often the posts you put the most work into and they flop and then you'll just literally...

Michelle Coulson (44:07)

Will (44:19)
kind of rip something off another platform and just post it on another one and go, you know, lol, and it will get like more likes than anything you've ever, you know, and we think we've all experienced that, but it's important just to keep going with it. What is it? What do people love to hear about from you?

Michelle Coulson (44:25)

I've noticed people love a recruiter bash on LinkedIn. They love a chance to air their grievances in their remote job search. And I can understand it because they're frustrated. It's a really hard market right now. So I love calling, hence the Remote Rebellion name, I love calling out companies who are not doing things the right way. So whenever I get the chance to be like, you're doing this wrong, you said this is remote and it's not remote, you're wasting people's time. I love doing that. And people love to get in on it as well. We're like throwing stones at the enemy.

Will (44:41)
Yeah, okay. Yeah.

Good, I like that. You're standing up for remote workers in a kind of William Wallace type way. You know, something like that. Braveheart. Right, good stuff. Well guys, thanks so much. I've learned loads. The hour has flown by. I really, really appreciate your time coming to talk to us about

Michelle Coulson (45:10)


Will (45:29)
my last question for each of you is where can people find and connect with you online? Chris?

Chris Cerra (45:34)
Primarily on LinkedIn, but if you want to see everything, just go to and you'll find a full list of everything there, all the different places to message me. And if you want to get a direct line for me, you have to sign up to one of the newsletters and then hit reply and all of those messages come right to me and I respond to all of them. So that's the fastest route to me.

Will (45:55)
Cool, I'm gonna put that link in the show notes. Michelle, where can people find and connect with you online?

Michelle Coulson (46:00)
Pretty much the same in terms of LinkedIn is the place that I'm there the most, but will have details of the kind of what I offer, how I help people to get remote work. Now and again, I'm on Instagram, usually posting more like where I'm working, the family that I'm spending time with and so on, but LinkedIn, Michelle Coulson from Remote Rebellion and

Will (46:24)
Cool. Well, look guys, thanks so much. Really appreciate it. Hope to chat to you again soon. Happy travels.

Michelle Coulson (46:30)
Thank you.

Chris Cerra (46:30)

Will Francis
Will Francis

Will Francis is a recognized authority in digital and social media, who has worked with some of the world’s most loved brands. He is the host and technical producer of the DMI podcast, Ahead of the Game and a lecturer and subject matter expert with the DMI. He appears in the media and at conferences whilst offering his own expert-led digital marketing courses where he shares his experience gained working within a social network, a global ad agency, and more recently his own digital agency.

Connect with him on Twitter (X) or LinkedIn.

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