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Ep: 183: How to break from the American norm and find your super power as a remote worker with Sam Kern

In this episode, I speak with Sam Kern who is a digital nomad who recently did a viral TEDx talk titled “The Surprising Power of Remote Work”. In the talk, Sam explains the often overlooked power of digital nomadism – how it can be leveraged to win back your time, pursue side-projects, do “life experiments”, and work with nearly anyone in the world. 

Sam is also the host and producer of Radically Different – a podcast series that explores lifestyles and career paths that break from the American norm.

Listen Below:

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Transcription:

Debbie:

Hey everyone! Thank you so much for being here. I’m really excited to speak with Sam. 

Hey Sam, how are you? 

Sam:

I’m good, Debbie. I’m excited to be speaking with you. 

Debbie:

Awesome. Can you tell us a little bit more about you and why you live an offbeat life? 

Sam:

Yeah, sure. So I graduated from college about two years ago. And at the time a lot of my friends were plugging into 9-to-5 jobs in the US, but I really didn’t have any desire to do that. 

So I actually ended up going on a trip to Vietnam with a friend and decided to stay. Since then I’ve been basically a digital Nomad; traveling and living abroad in different places. 

I work part-time, remotely,  as a software engineer, and the rest of my time, I produce a podcast called Radically Different which is like this exploration of lifestyles that break from the American norm. 

How am I living an offbeat life? I think the biggest difference is that I’m location-independent, I move around a lot and I really have been focused on following my curiosity over the past two years. And I found that this combination of location Independence and part-time remote work has really allowed me to do that. 

And because of that, I’ve been able to have a lot of really cool experiences and I’ve also realized that it gives me sort of a leg up when it comes to building my career and working with people that I most want to work with and to pursue my passion. 

So yeah, hopefully, that answers the question at least a little bit 

Debbie:

Yes. It definitely has.

When you were still in school, what was your major? 

Sam:

I was studying computer science and I had a minor in Hispanic studies. 

Debbie:

Did you ever think that this was going to happen or it was something that just happened to you? 

Sam:

It’s funny Debbie because when I was a freshman in college, I didn’t know what I wanted to study. I was feeling kind of lost and my roommate studied computer science and he sort of introduced me to the world of computer programming and entrepreneurship.

I remember thinking at that time like, “Wow, this is so cool that I can build things with nothing but a laptop,” and I was thinking, “Wow, this means that I could be really mobile. Like, I could probably be anywhere in the world and be creating things.” And I love that idea.

It’s funny because I wasn’t really thinking like, “Oh when I graduate college I’m going to become a digital nomad,” but there was sort of that idea in the back of my mind. I’m like, “That’s something I could do.” 

And yeah, it afforded me a lot of freedom to be able to pursue the lifestyle that I want.

Debbie:

What was that moment like when you were in Asia and then you realized that this was something that you wanted to do long-term? Was there an aha moment or it was just because you really loved it there?

Sam:

There absolutely was. So basically a friend of mine said, “Hey, let’s go to Vietnam on a three-week trip.” We did that and at that time I decided I was interested in starting this podcast and I also brought my laptop and in the back of my mind I was thinking like, “I could stay if this place is exciting.” 

And sure enough I met a bunch of digital nomads and people who are westerners, who were living in Vietnam. The day that my friend left, it was like the first morning that I was alone in Saigon, in Vietnam, Ho Chi Minh City. 

I was like, “Okay, I guess this is the moment that I’m alone here in this country, and the moment that this podcast is going to start.” And I have been traveling, backpacking for 3 weeks, wanted to start feeling productive, and wanted to start a podcast. 

And so I basically searched for co-working spaces in Saigon. And the first it popped up, it had like a come rent a space for free on Tuesdays and it was Tuesday. And so I was like, “Okay!” so I just basically hopped on my motorbike, drove across the city, and entered this like a three-story co-working space filled with foreigners that were working there.

And I honestly kind of have my mind blown because I had known that like there were people doing this. But this is like my first real encounter with like, “Okay, here’s an entire co-working space filled with westerners who are on to something that I may haven’t realized yet.” 

I ended up spending three or four days doing interviews with people and I ended up finding this crazy story of like these entrepreneurs in Saigon who were basically taking advantage of the low cost of living, the massive growing middle class, and this sort of lag in services that we are accustomed to in the US and they were basically copying those ideas. 

Ideas like Uber and bringing them to Southeast Asia. And it turned into this crazy story – the first episode of my podcast. But I remember thinking like day 3, I got done with interviews and I was like, “Oh my God. This is crazy. “Like, first of all, the story that I’m finding, the lifestyles I’m witnessing like, “Wow, this is really fun.” 

Like I sort of discovered this passion for podcasting, for interviewing, and for storytelling. I would say that was the moment it was the sort of feeling of exhilaration like anything is possible. I have the freedom to move around and to really expand my curiosity and that spark of curiosity that comes from stumbling upon new things that are just interesting. 

So yeah. There was definitely that moment there.

Debbie:

It’s really amazing when you think your idea is out of the norm and then you get into a spot or you meet a bunch of people that are living it. And then you’re like, “Well, this is not as impossible as I thought. It’s just the group of people that I was in or maybe the society that I was surrounding myself with that just thought it was abnormal.”

But then, you go to places like where you are or even Chiang Mai and there are so many co-working spaces and people living their life in a totally different country with this whole new mindset that is mind-blowing for somebody who has never seen this before.

So that was a great spot for you to be in.

Sam:

Totally and, Debbie, that’s kind of like my whole thesis. Like, that’s what the podcast is really about: exposing people to people doing life in ways that they’re unaccustomed to write. I really believe exposure to radically different ideas really just broadens your perspective on what’s even possible. 

So yeah, hundred percent. It’s like you think something’s outlandish and then you and then you find good people that are doing it. And on top of that, if it’s something that you’re interested in doing, I think it’s so much easier to do if you’re surrounded by people who already figured it out. Otherwise, you just feel like you’re crazy about it.

Debbie:

It’s like being in a mastermind group and it becomes so much easier instead of just Googling everything for yourself and it takes so much longer to do that. 

Sam:

Yes, exactly.

Debbie:

After the 3 days when you did your interviews and you probably realized by then that, ”Okay, this is where I need to be, the path that I need to be on is this,” did you do anything to prepare for this so that it could become more sustainable? 

Sam:

Yes. So a few things, the first thing I will say is that, in a way, I was just on this great adventure. I really felt like I was just on this adventure and I was just I think, especially because the cost of living is so cheap in Southeast Asia, I had enough runway that I knew I could sort of exploring comfortably for a while.

And I was kind of just have the mentality of like I’m just going to go until it’s clear that I need to do something else or figure out how to make money. But I will say after about a month, I went to Thailand and I was like, “Okay. I need to start figuring out how to make a living.”

And so, I have my laptop, I knew how to code, I had a little bit of software development experience. I basically just went on Upwork and started perusing job postings and I applied for a few and ended up getting the first one I applied for actually.

And it was a very kind of grueling and demoralizing process as I think like any time you’re looking for a job it is. But I sort of just hustling really hard for two weeks. And yeah, within two weeks, I landed my first client.

So that was great because I was also able to find a client that only needed like 15 hours a week of work done and it was super flexible. Like, it was 15 hours a week – the weekly check-in. The level of freedom that experience for the first time in my life was insane because I basically would work maybe two days a week and it could be like on the weekends if I wanted.

And then the rest of the time I could just do whatever. I explored Thailand on a motorcycle. I even like worked 7, 8 hours on a ship, on the way to Koh Tao to get my scuba certification. 

So yeah, I found a way to make it sustainable and I just really felt alive and like I was on an adventure.

Debbie:

It’s kind of like Pandora’s box: once you open it I don’t know how you can get back to what you thought was normal because it’s such a different world when you realize that you don’t have to live a certain way that everybody told you you should be living. 

And it makes you so much happier when you have that freedom and you figure out that it can be sustainable.

Sam:

Totally. But it’s interesting ‘cause there’s always pros and cons of everything and this is something I try to cover in my podcast too. I felt that level of freedom and I wasn’t willing to go back – once you’ve experienced that.

Basically, I came back to the US for Christmas, and then a friend’s company offered me a job. Like, they wanted me to work for them. And I said I’ll only do it if it’s part-time and remote because I figured this thing out. I figured out that I can support myself only working 15, 20 hours a week. And so I’m not willing to give up on that. 

So yeah. Sometimes I don’t know how people…  Especially in computer programming, maybe it’s just me: I don’t know how someone codes for 40 hours a week. There’s so much time in front of a screen, sort of like, by yourself in your own head.

But I will say that it’s a strange thing. Like, once you have that freedom of I can go anywhere and I can spend all this extra time doing anything, it’s almost like the paradox of choice kicks in where you’re like, “Where am I going to go?” 

And I found that one of the practices that I’ve been trying to do is pick a place and invest and stay for a while because I need to put a bouncing around a lot of different places and it got kind of draining. 

So that’s kind of been my focus and my meditation over the past several months. Like, take it a little bit more slowly. 

Debbie:

I think in the beginning we e all start that way, right? We have checkboxes we need to fill with all of the places we have to go to and then as you go longer and longer, you realize that it’s actually not that good for you if you want to do this long-term, and you also want to start working.

At least for me, it didn’t happen like that ‘cause you want to see everything then you don’t have the time because you still have to work and then you’re still traveling so it’s pretty nuts. 

Sam:

Totally. I think that trying to mix travel and working, at least working hard, doesn’t work that well for me. It can work but it’s just less fun. 

So I would either be going to be somewhere for a while and do like two or three days a week I’m working and then I have like three or four days off to just explore or kind of do it more of the traditional way of like coming to work for several months and then I’m going to take several months off and just travel, explore, pursue new hobbies. 

Debbie:

And I do have to say it takes some time to find your groove with all of this because for some people that actually do work for them to constantly travel and for some people, like you and I, we’ve realized that it’s not sustainable for us. 

So it’s just finding out where you are and the balance between the both of them. 

Sam:

That’s true.

Debbie:

Of course, I also want to talk about setbacks because these are not just great things. There’s a lot of things that you encounter as a freelancer, as a remote worker, as a digital nomad. What has been the biggest setback that you’ve encountered so far?

Sam:

That’s a good question. I think the biggest setback has really been over commitment for me. There are so many things that I want to do. There are so many things that excite me and I want to do them all at once and that’s the problem.

For instance, when I first moved to Medellin, Colombia, I was transitioning out of a client work. I had started with this new company and I was trying to get the podcast out. And so, all these things meant that I was just slammed. 

I was working 6 days a week, sometimes 7 days a week, and just feeling super drained and overcommitted. 

Similar thing when I was in San Diego. I was working with this guy, Pablo Fernandez, who has like an experiential dinner company and I was doing work with him and helping him produce their events. But I was also like doing the podcast, I was also planning a co-living experience, and I was also preparing for a TED talk. Like it was just too many things.

And so I think I don’t know if it’s like setbacks but that’s really what I realized that those have been a weakness of mine. And those have been the times where I become overcommitted and relay do nothing very well. 

So yeah, I think maybe that’s more of a personal struggle but that was the first thing that comes to mind.

Debbie:

I think we want to do everything all at once and sometimes you don’t feel very good about yourself and you feel like you’re not doing too much. And I always find that when you actually take a step back and just do one thing at a time, you get more done. So that’s the irony of it all.

Sam:

Yep, learn that the hard way. 

Debbie:

Since you’re constantly on the road, obviously, you’re also working there, how much money do you save while you are traveling around and how are you able to make that last? 

Sam:

That’s a good question. Right now because I’m actually an employee at a company, I just auto draw savings. So basically there’s a percentage of my paycheck that I just never see and it just goes straight into an investment account and part of it goes straight into a savings account. 

And so, that’s worked well for me because then it’s just like whatever I have left is what I have left to spend.

Debbie:

It’s all about automation. I love automating things because I constantly forget things. So whenever you have the time to do that or you’re able to do it – definitely automate things, especially when it’s bills. On my goodness, it saves you that headache of being late with payments and all of that. It’s just nuts. 

Sam:

Yeah. I think I’m particularly fortunate because software engineering is in such high demand, right? The salaries are higher and so, I’m in a position where I can put aside 10% to 20% of my income each month and still have plenty of money to live a comfortable life and working part-time.

I will say that’s also in part because I’m a minimalist. And I really try and reduce across-the-board the things that I spend money on. I don’t have a car, my biggest expense is probably plane tickets. Because I’ve been living in cheaper places, my cost-of-living, at least, for rent is pretty cheap. 

I really say and this is something I really elaborate on in my TEDx talk, it’s like reducing the number of hours that you’re working while at the same time reducing your costs. ‘Cause I think we can live on a lot less actually than we think. And that’s an important piece of that. It’s the last sexy piece but I think that’s important as well. 

I mean, if you want to prioritize your freedom and your free time, prepare to make some sacrifices in that regard as well. 

Debbie:

Yeah. It’s just figuring out what really works for you and what your balance is and what you’re going to be happy with. Because a lot of people want certain things and you sacrifice. Thanks for that as well like more freedom. You have to work more to get that.

So, if you don’t need all of the bells and whistles, you can live like Sam does and have more freedom to do other things with it. Like, more experiences for example.

Sam:

I don’t know if you read the book: I Will Teach You to Be Rich. Have you read that, Debbie?

Debbie:

No.

Sam:

It’s a super schemy title but it’s a fantastic book on personal finance – I swear. And one of the things that he talks about is that what he encourages people to do is to choose the things that you really love and feel free to spend as much as you want on them. And then decide what are the things that I really don’t care about and slash those expenses to a certain extreme level.

And so I think that’s a nice framework of looking at things. It’s like if what really makes you the happiest is traveling a lot and you want to spend 50% of your income on plane tickets – great, but then you just need to decide what are the things that are not important and really slash those aggressively.

Debbie:

And now, well, during this pandemic we can’t really travel so you’re saving more right now. So when borders start opening up, you’ll have a ton more savings to spend on that if that is what makes you happy. So that’s a good thing in a way.

Sam:

Totally.

Debbie:

When you first started applying for jobs, because I know you said that the first one that you’ve ever gotten was through Upwork, how did you prepare for that moment? Because a lot of the people who are doing this, they maybe don’t have remote skills or they don’t know how to actually transfer that into remote work. 

How are you able to do that especially since it was your first time out? 

Sam:

That’s a great question. Yes. So for me, there were a few things: one is that I have had a little bit of experience working as a software engineer for different companies. Like summer internships. I worked during the summer after graduation. So I had a little bit of a portfolio but not as much as you would hope from a software engineer who’s created a  profile on Upwork.

The second thing is that I had quite a bit of entrepreneurial experience. I started a startup when I was a sophomore in college and because of that I really understood what someone was looking for when hiring for a software engineer. 

The reason that I won this first client was because my proposal to him was really about like, “Hey, I’ve been in your shoes before. I know what it’s like to be a startup founder. I know that you’re looking for a software engineer who understands your vision, who is incredibly reliable, who can communicate really well with you, is going to be like a team member, and it’s going to help you build this thing.” 

To be honest, he didn’t exactly know the path forward and I think that’s the next level as a freelancer or consultant: you actually want to help people see the path forward. Yes, they’re hiring you to build something but they’re also hiring you to sort of giving them advice and leadership and on how to build that thing. 

So really I was then getting compared. It was like me versus a bunch of development agencies where there weren’t really a lot of them. Like attention being and personalization being put into their proposals. And so that’s how I ultimately won the gig.

The other thing that I did is that I priced myself a really low at first. And I think that’s something you just maybe have to do if you’re starting out, if you have no track record on Upwork or whatever the job site that you’re using. And if you don’t have a huge portfolio, that’s a way that you can sort of like undercut the competition and be more marketable as a starting point.

So, those are the things I would recommend. For me, software development is always typically done – all the tools are kind of done online. I think what we are seeing right now with the covid-19 pandemic is that more and more things are going online. 

I think there’s really no excuse now. I mean, there’s a lot of professions now that are going to be done online and done remotely or at least have the capacity to be down that way. So I think it’ll be more and more a possibility for people.

Debbie:

It’s less excuses for people. “They can’t do this. No, it’s too hard.” Well, you have no choice now. 

The two things that I really want to point out are first: how personalized that message was to that client you had which is really great. I think a lot of times, I mean, I’ve hired people before and when they send you the resume cover letter, it’s like sending mass emails and you know for sure that this is like copy and paste.

And that’s one of the things that I always point out to people when they ask me about this – never do that because people can see that. And they’re not going to interview you if you don’t even put in the time, the few minutes of time to really personalize that.

 And also really understand what that company or what that small business needs and you were able to really do that within those just a few words that you even shared with us which is really amazing. 

And also another thing is a lot of people are probably saying, “Well, I don’t want to undercut myself or my value,” but if you’re beginning, you really have no experience, we’re not going to pay you top dollar. And we’re the ones really guiding you and teaching you as well. 

So think about it as a learning experience and then as you grow and as you learn more, it keeps adding to your resume and then you keep getting higher and higher pay that you don’t need to be at that same level. 

It’s in the beginning, it’s not the whole thing. You’re always going to be making that salary and the payment for yourself higher and higher which is a really good thing to do especially if you don’t have any experience yet. So I love that. I love how you got your first client there, Sam. That’s a really good way of doing it. 

Sam:

The only thing I’ll say, Debbie, that I’ll just add on to that is the other thing I did. These job sites can be kind of overwhelming because there are so many posts and you can easily feel like, “Who am I  to respond to this proposal? How I’m actually going to stand out from all these other people around the world that are competing for the same job?”

So, I’ll also say that it’s really important. Like, as you’re looking at these jobs, as you’re searching, only spend time on the ones where you’re like, “Oh, I totally have the experience,” especially when you’re starting out, focus on the job post where you’re like, “I’ve already done something like this. I’ve already built a product like this. I’ve already used these tools and these frameworks whatever it is.”

Because that’s really important too. When I saw this job, the first one, it was clear like, “Oh, I’ve already built something like that.” And then, I was able to say, “Hey, I’ve already built this. I can build it for you.” 

Debbie:

Yeah, I love that. It’s such a great way of landing that first gig especially if you’re just a newbie and even for people who have been doing this for a little while, they still need some tips and tricks like that because it can get really, like you said, super competitive. And especially now there are more people needing to work online because we have no choice, unfortunately.

Sam:

Yeah. The last thing I’ll say too is that it can be grueling. Like, when friends of mine are in the midst of a job search, I’m like, “Yeah, that probably sucks.” 

Just know that that process can kind of sucks because you feel like you’re in a place of vulnerability, you sometimes feel like you’re asking for something which actually you should think about it the other way but like you have the opportunity to provide value to someone.

But just know that it might be a bit of a process. It might take several weeks or months to land that first client. You just need to get that first one and then you’ll figure it out as you go.

Debbie:

Yeah. It’s just persistence. You just have to keep going. 

Sam:

Yeah.

Debbie:

Let’s fast forward to 50 years from now, Sam, and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for? 

Sam:

Wow, that is a big question. A few things that come to mind. First is that, for me, I’ve kind of stumbled upon, I would say, sort of a radically different lifestyle but it has to do with location independence. 

This idea of a global citizen. This idea of everyone being an entrepreneur or sort of solo creator in some way. And it has to do with people who are out on their own building something meaningful in the world. 

And so what I have found is that it still feels like there’s not a lot of systems and structures that people can plug into to feel supported in that journey. And there’s more and more of that coming but I think about what my life’s work or legacy would be. 

I think part of it is going to be related to building those systems and those structures so that people who want to live in a radically different way can feel that there are other people that are doing the same and can feel uplifted, inspired, motivated, and supported by other people in the similar position. 

So that would be a piece of it and then I think another piece is that my whole life I’ve been really interested in how do you create spaces or use technology to help people connect in a more meaningful deep way. 

And that’s why I was drawn to this apprenticeship in San Diego of working with a community builder who helps people unite and connect more deeply around food. And so I think about, “Okay, my legacy. I want to be known as someone who created spaces where people can connect and there’s a sense of joy and aliveness.”

So we’ll see how those things manifest but I’ve got some ideas and yeah, that’s the loose plan at the moment.

Debbie:

Well, that’s gonna be an exciting 50 years.

Sam:

Yeah. We’ll see where things go. I also think it’s like that question is hard because part of my point is the journey is the destination. And what I’m talking about is following your curiosity and in a way, it’s like I don’t really know. 

I think having a sort of idea of what you want to create long-term can be nice but it’s also letting yourself sort of giving into the journey of it all. And so, as long as I’m continuously curious and doing the things that make me feel most alive, I think that’s the priority.

Debbie:

There’s always constant change too. So you’ll never know where one thing leads you so that’s really exciting most of the time. 

Sam:

Yeah, most of the time. And then sometimes you’re just like, “What am I doing?”

Debbie:

Now, Sam, if our listeners want to know more about you where can they find you? 

Sam:

Yeah, so you can check out the podcast Radically Different at RadicallyDifferentPodcast.com. And feel free to reach out to me via email there. I’m also on Facebook and Instagram, the handle on both of those is @radicallydifferentpodcast. 

And yeah, I love receiving messages. I send a lot of voice messages back so just prepare for that.

Debbie: 

Thank you so much, Sam, for being here with us today. I really appreciate it.

Sam:

Thanks so much, Debbie. It was such a pleasure.

GET THE EXTENDED INTERVIEW WITH SAM WHERE HE SHARES HOW TO QUICKLY BUILD A COMMUNITY IN A NEW CITY BY HOSTING 2ND-DEGREE DINNERS.


Show Credits:

Audio Engineer: Ben Smith


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