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I recently joined up on a trip with Hacker Paradise to meet up with some other Digital Nomads who are all living their best nomadic life. And while working in Seoul, I sat down with the former CEO of Hacker Paradise, Spencer Jentzsch, to source all of his knowledge about the world of remote work!

We talked about pros & cons of working remotely, the different jobs you can do remotely, and the realities of actually living a digital nomadic lifestyle. And he gives some great tips on how to approach your boss to let you work remotely.

You can watch a video of the interview or read the condensed transcript below. ( And if all else fails grab yourself a copy of my finally fully remote map. )

The below interview has been edited for clarity and brevity.

How did you make the transition from working a more traditional style job to working fully remote?

Spencer: I used to teach Korean at university and then I did project management for a software company in the states. And so when I was doing that software job, I was consulting a bunch and traveled a bunch. Which in my head that’s like a little bit of nomadic. Like during the week I would go and work from a different location.

Then I just got sick of it, I said “I’m going to go return to like roots of living abroad and doing different things.” And that’s when I stumbled upon the whole digital nomad lifestyle. And I took my current job and really tried to make it work nomadic and they said no. So I said, screw you, I’m leaving. And I quit.

And that’s when I came here. My first time being a nomad was actually when I came and joined Hacker Paradise and I was supposed to be a participant and doing some of my own projects. I thought I’ll do this for a cheeky little summer and see how it goes and then go back and get what my mom calls an “adult job”. And then I ended up working for Hacker Paradise and I have been out on the road for three years.

You’ve seen a lot of different types of jobs that people are able to do remotely. Can you talk about the variety and range of jobs you’ve seen people make work?

Spencer: I think a lot of people can do it way more than you generally think. So you’ll see a lot of people on the road that are engineers or graphic designers or entrepreneurs. Those are like really common things you might see. Or like someone who’s writing online or doing some sort of digital marketing or advertising, those are pretty common.

But especially for tech companies, there’s a lot of jobs that have moved to remote. So whether it’s HR or marketing or PR or any of those things, those companies are really advanced in remote policies.

We also have seen while I’ve been out here, lots of jobs that you don’t think would work remote find a way to do it. So we’ve had people with us who are doctors or nurses and do some sort of telemedicine or management.

The other one that I always see that surprises people is real estate. So we’ve had real estate agents that come with us. You think, “how do they show a house to somebody if you’re not there?” Well you realize that that’s not the only thing that you really have to be there for. So they do all of the finding clients, interacting with them, finding houses, and then setting everything up. And then they have an assistant who then will do the showing of the house and then everything else is online.

For a lot of us, we think, “Oh, I can’t do my job remotely because of this or this or that.” Well, there might be an option to just take that piece and leave someone to do it in person or find some other way to do it electronically or remotely. There’s a lot of ways to, to figure out how to do things remotely.

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Do you have any tips for people who want to start working remotely but love their job or company and don’t want to leave? How do they start that conversation with their boss?

Spencer: I generally tell people to make a business case. Think it through, make a presentation. Be really upfront about the pros and the cons because you can’t just like sell this half baked idea. And then things like, I won’t tell them about the parts that are difficult and maybe they’ll just not realize it until later. They’re going to figure it out!

We usually have people start be talking about the perks. Like the perks of working remote is generally your employees are more happy. When there is a higher retention of employees at the company it is really good for staff happiness. They get to network with a lot of different people. They can learn and do new skills while they’re abroad.

Then we have people talk about the cons. The biggest of what’s most difficult generally is time zones and communication. So we tell people, let’s address these up front and then you can talk with your employer about here’s a potential problem. Now let’s talk together about a strategy, about how we can work to avoid this becoming a bigger problem.

So we have people present a case and usually an employer is really impressed that you’ve gone through the whole effort and you’ve thought it through.

For a lot of employers as well, they are worried that you might just go and be on vacation and be pretending to work. So for people who are thinking of doing it for the first time, a lot of times coming with hacker paradise is really comforting to an employer. It’s like this person isn’t just off on the beach doing whatever, they are with a group of other professionals. And from an employer’s perspective, that’s really comforting.

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    As someone who actually runs a fully remote company, from a boss perspective, what are the biggest challenges to having a remote team?

    Spencer: Different, it’s very different. I have employees that I have never met in person. I’ve chatted with them over Skype and email and slack and all the online tools we use to communicate. And usually I try to travel around and see them, but one of them has worked for me for almost a year and I’ve never met her. And that’s really strange for a lot of people.

    It’s really important for us when we’re hiring and we’re interacting with people to try to do lots of activities to get people to connect. We have ways to have the team get to know each other even if they never meet each other in person because you don’t realize this a lot, but just the daily interactions you have with people, build a rapport, which then makes it easier to work together.

    Are there any locations that are harder or easier to work from?

    Spencer: For me because I do a lot of work across a lot of times zones, Asia can be difficult. I feel that I wake up for meetings at eight in the morning and then I’ll have meetings at 11:00 PM. So for me of that’s like me not structuring my day correctly and I’m just working all day. There are more Digital Nomad friendly cities though.

    Right now with my job, that can be really difficult. Before I used to live here and when I didn’t have as many meetings, it was no problem. Besides that, if the Wifi is crap, then like nobody’s happy. So there’s a lot of beautiful tropical islands that I would love to go to ’cause I love the beach. I love being in the water, but if it doesn’t have a solid wifi connection is just a nonstarter for me.

    You’ve been doing this for three years now. Is there something that you’ve seen within this remote work, travel, digital nomad industry that you really don’t like?

    Spencer: I don’t like when people only talk about the lifestyle through rose colored glasses because like anything, there’s great things about it and then there’s things that are difficult. You have this person get an article published in the New York Times will write about like, “how I’m making my life as a digital nomad and I’ve never been happier and I’m making more money than I’ve ever made.”

    And like, I don’t know, maybe that person just has a really lovely position and a really lovely life, but that’s not the case for me. I mean when I came out and started to do this, I took a big pay cut because I valued the lifestyle more than the money. And I think a lot of people do that.

    I think a lot of times people get really lonely on the road and that’s one of the reasons that I really love traveling with Hacker Paradise and why I recommend it. Because then you’re with a group of people that you get to know and it’s like your family and support structure on the road because if you’re traveling on your own, you don’t have that.

    Of course the good things still outweigh the bad, but it’s not like a perfect paradise charmed life, which I think people at home think a lot. And sometimes the narrative that people push through blogs or whatever seems to be Instagram scene, it’d be like just rosy all the time.

    And so that’s like the thing that I think people at home should know is it’s not just all day on beaches and having the perfect life. Things are difficult. If you think having a relationship is hard at home, try having a relationship on the road. It is wild and crazy and not very long lasting.

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    What do you see as being the future of remote work?

    Spencer: More of it for sure. There has been studies that talk about how by the year 2020 about half of the workforce in the US will be remote in some regard. Whether that is you can work from home a couple of days a week or you’re fully remote. So the trend in the workspace is definitely going that way.

    So I think we’ll see a lot more things pop up to address some of the negative things that we’ve talked about with remote work. And I think we’ll see over the years there’s more digital nomad visas that start to pop up. Governments are the slowest thing around. So it might not happen for like 50 years, but like things are starting to happen.

    Things to address loneliness, I think you’re gonna see pop up. We’ll start to see more communities on the road similar to us that provide that social structure. I think that’s going to be even stronger. So lots of these things to try to help the current pain points of remote working in digital nomadism I think is where the industry is going.

    Is there anything else that you want to add about remote work in general or something I didn’t ask you about before?

    Spencer: Hacker Paradise, if you’re interested in Hacker Paradise, come check us out. We’re great.

    The other thing I tell people, that I try to like dispel is, people will talk about, “oh you want to work remote, quit your job and move to Bali and figure it out.”

    And I always tell people no, like slow it down and don’t just quit your job and move abroad and live off your savings! And then hope something like comes together as you go. Like take some time to think about it. You’re making a big career shift potentially. So have a plan. (Like my My 5 Step Process to becoming a Digital Nomad type plan 😉 )

    If you’re like, “I have this plan and I’m going to do this and I am passionate about this,” by all means go for it. But don’t just quit your job and move and live off your savings and hope something comes together because those people in my mind are aren’t sustainable.

    There are people that are like doing it short term for 3-4 months until they run of money and then they go home, burned out. They go home without money and they go home and maybe they had a great time, but it’s just, it’s different than I think the people that you and I see on the road. People that are like remote working professionals who have a career they care about and can do this sustainably.

    And I think a lot of it is just having that plan when you go and say, this is what I want and not just I’m going to go and see what happens. I always tell people that’s like the worst advice that blogs will give.


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