When it comes to digital nomad careers, the tech industry can be a goldmine. Since the most important equipment in these jobs are typically computer + internet, travel coder jobs may be a natural choice for someone who wants to travel and work remotely.
That said, you don’t often meet people who’ve actually taken the plunge and hit the road. Dave Trabka is a great example of someone who did.
After spending part of his career in finance, Dave stopped to ask himself if this was really what he wanted to do with the rest of his life. He discovered a program called Remote Year, which reoriented a lot of his life and set him down the path he’s on today as a Full Stack Developer at Innovation Department in NYC.
In today’s episode, Dave joins us to talk about how to become a digital nomad and travel and work remotely.
This episode was transcribed with the help of an AI transcription tool. Please forgive any typos. Laurence Bradford 0:08 Laurence Bradford 0:23 Laurence Bradford 0:44 Laurence Bradford 1:06 Laurence Bradford 1:53 Dave Trabka 1:55 Laurence Bradford 1:57 Dave Trabka 2:07 Laurence Bradford 2:43 Dave Trabka 2:48 Laurence Bradford 3:00 Dave Trabka 3:37 Dave Trabka 4:53 Dave Trabka 6:39 Dave Trabka 8:09 Laurence Bradford 10:21 Dave Trabka 10:57 Dave Trabka 12:43 Dave Trabka 13:40 Laurence Bradford 14:37 Dave Trabka 14:49 Laurence Bradford 15:50 Dave Trabka 16:38 Laurence Bradford 17:44 Dave Trabka 18:12 Dave Trabka 19:18 Dave Trabka 20:42 Laurence Bradford 21:13 Laurence Bradford 21:19 Laurence Bradford 22:31 Laurence Bradford 23:37 Dave Trabka 23:43 Laurence Bradford 24:29 Dave Trabka 24:57 Laurence Bradford 25:01 Dave Trabka 25:05 Laurence Bradford 25:09 Dave Trabka 25:23 Dave Trabka 26:11 Laurence Bradford 27:06 Laurence Bradford 27:42 Dave Trabka 28:08 Dave Trabka 29:07 Dave Trabka 30:28 Dave Trabka 31:34 Laurence Bradford 32:13 Dave Trabka 32:42 Dave Trabka 33:32 Laurence Bradford 34:16 Dave Trabka 35:21 Laurence Bradford 35:47 Dave Trabka 36:56 Laurence Bradford 37:10 Dave Trabka 37:24 Dave Trabka 38:30 Dave Trabka 39:50 Laurence Bradford 41:14 Dave Trabka 42:12 Laurence Bradford 42:48 Dave Trabka 42:54 Laurence Bradford 43:10 Dave Trabka 43:12 Laurence Bradford 43:19
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Hey listeners. In today's episode I talk with Dave Trabka. While working in finance, Dave stopped to ask himself if this was really what he wanted to do with the rest of his life. He then discovered a program called remote gear that reoriented his life and set him down the path that he's currently on today as a full stack developer. I reached out to Dave for this podcast because he learned to code and then use his skills to travel abroad, which is something I know a lot of people would love to do. In our conversation, Dave talks about how he worked abroad, what working on the road actually looks like, and the pros and cons of traveling full time. If you'd like to become a digital nomad or simply travel more, this episode is for you. Enjoy.
Hey, Dave, thank you so much for coming on the show.
Yeah, of course. Good to be here. Thanks for having me.
I'm really excited to talk to you today. About your experience and working and traveling and all that. But first, Could you just tell us a bit about what you're doing today? Currently?
Yep. So I am currently a full stack developer for a company called Innovation Department. We, we kind of refer to ourselves as a tech studio. We have we have a few different brands underneath the innovation department, umbrella. I'm primarily working across some of our e commerce businesses. You know, some natural health supplement businesses. I started here just a few months ago actually following kind of a career change into software engineering.
Nice, nice. Um, and where are you based? Just to give the listeners some context?
Sure. Yeah, we are in New York City. I'm in the Soho neighborhood, which is an awesome part of New York to be in. Much better than the the chaos of Time Square that I used to work in. Next door too.
Oh man. Yeah, I go through that everyday Actually, I live in Manhattan as well. I used to live in Brooklyn, but now I live in Manhattan I on the Upper West Side, which I really enjoy. But I do have to cross through all the timeshare craziness. But it can be kind of fun sometimes because it makes you feel like, I don't know, makes you feel kind of like really grateful to live in New York, because so many tourists are there to come visit New York. So it's like, it's very, like, you know, I feel very appreciative. But then if you're really in a rush or something, you're like, Oh, my gosh, I am moving here. Oh, yeah. But you weren't always in tech. Right. So what were you doing before?
Yeah, no, tech was kind of a big career pivot. I studied finance and entrepreneurship. undergrad, started my career in investment banking, here in New York with Bank of America, Merrill Lynch, working in their industrials and m&a groups. So for a few years, I was just kind of grinding in a cubicle, working on m&a deals. And just, you know, not super happy, didn't love the lifestyle eventually ended up moving over to a small private equity firm in Chicago was supposed to be a little bit better of lifestyle, which it certainly was. But at the end of the day, I just didn't feel that kind of that transactional finance that m&a world was really for me. And I came to a stopping point where I just kind of self internalize, and ask the question, you know, is this what I want to do with the rest of my life? And it was a really quick answer that no, it was not. So I decided to explore what other opportunities might be a good fit for me. Both professionally personally, started interviewing with with startups both both on the east coast and the West Coast.
So I pretty firmly made my decision to leave finance I hadn't yet done it started interviewing looking for the next gig. got pretty far in some processes. And around the same time, my friend, Mike, I was sitting at dinner with my friend Josh and and he brought up this program called remote year and he was like, yeah, you basically like you quit your job, and you go on the road for 12 months, and you spend one month in 12 different cities. Like he worked for this company. And at the end of the day, that's not actually what remote year is we? Almost everybody has this twisted perception that you just kind of like quit your job go on to remote here and work for remote here. But we can get into that later. But uh, you know, I looked at him and I'm pretty sure I said, you know, like, you're crazy man. Like, I'm not quitting my job to go travel the world for a year. But the longer the longer I thought about it, it wasn't really Oh, why would I do that? It was more of a Why not? So I ended up weirdly through the grapevine back when I was at Bank of America Merrill Lynch, I worked with another girl who was in my analyst class move to Chicago was there at the same time with me also in private equity. And we, I forget how it even came up. But we were having a random conversation about this remote you thing and I was like, Hey, you know, who wants to do this with me. And oddly enough, her boyfriend had actually gone to the University of Michigan with the co founders of remote year and he put me in touch with I think, employee number three, a guy named Jesse gross, who's a really awesome guy and Jesse and I connected, basically just to for me to ask him a few questions, learn about the program. And he ended up just accepting me on the spot.
So I got accepted to remote year was still interviewing with a few companies on the West Coast that I had strong interest in. And I basically gave myself the ultimatum, if any of those opportunities on the West Coast worked out. I was moving to San Francisco. If they didn't, I was going on remote here and finally when I heard back from When I got the last rejection, I guess, to put it plainly, I committed to remote years. So, in August 2016 I boarded a plane to Kuala Lumpur, Malaysia, decided to set up an LLC and start a consulting business. I was hoping to to consult with small startups that needed advice on things like strategy, finance, operations, help them fundraise things that that I had been on the other side of the table when I was working on m&a deals and and looking at investments from a private equity perspective. So I start this consulting business and my my first client was one of my best friends growing up, he had a real estate tech business. He was starting in New York City basically providing property management tech to mom and pop, multifamily apartment building owners, your walkups in New York, not these high tech luxury buildings that have elevators and you can pay rent online. So I spent the year trying Traveling with remote year, bouncing between city to city every month while helping my friend Mark build built his startup Bixby.
Yeah. Awesome. I really want to jump into a few things that you mentioned. But full stack is actually one of the sponsors of our podcast and I've worked with them a good deal in the past so definitely familiar with their with their boot camp. Yeah. And anyone who's listened to the show, a lot has definitely heard other guests. I think we had to be the founder on a previous season. So yeah, lots of internal apps there. But I would love to talk about remote year a bit. And could you explain more about like the program itself? Like what it's actually like, do you have to travel for a full year? I know listeners would would love to learn more about that.
Yeah, definitely. And and remote year has certainly evolved. Over the years when I joined in August 2016, only one single program had ever finished. I was in program number seven, it was a group called Liberte them. But today remote yours is kind of a much broader platform. They've got some venture backing that's allowed them to pivot in some ways, but stay true to the core and others. So fundamentally remote year was started as a program that you would join with anywhere from call it 50 to 75 other people, you come in with a job that you can take remotely so you don't end up working for remote year. Remote year does not provide you with a job. You either negotiate with your employer to go remote. Maybe you're a freelancer, so you kind of control your own destiny, things like that. And basically, remote year provides infrastructure and logistical planning to allow you to live in Any given country for a month at a time so when I joined like I said in August, I flew to Kuala Lumpur, Malaysia, I spent three months in Southeast Asia. From there we went to Thailand, then Cambodia. Then we popped over to Europe spent a month in Split Croatia, in Prague in Lisbon, and then made our way back to lat am Mexico metazine in Bogota, Colombia, Lima, Peru, and then finished it off in Cordoba, Argentina, and when Osiris So basically, throughout that process, remote year provides you with an apartment, it provides you with access to a co working space, so you can actually, you know, do that remote job.
Today, it also provides you with some programming in the cities, they'll plan some small events, they call them track events where basically you sign up for a track of event. It could be like four events, there might be three different tracks. So you pick whichever one resonates with you. And I think one of the most in interesting parts about remote urine one of the highest value ads is the fact that they actually have city teams in each location you go to so they have two people who are locals to that city or that country who are just resources, they help you plan events, they'll help you, you know, communicate with people. If you don't speak the language. You know, I I have a really fun story about losing my passport in Malaysia. Seven days before I had to officiate my sister's wedding, so they have legal resources that will come help you deal with immigration and the police station to file a passport loss report or whatever it's called.
So they provide you with a lot of resources you might not be able to find traveling on your own. to your question about length of time, how long do you have to travel is it a full year? So we're about your started as 12 month programs, they now also offer a four month program which provides you a little more flexibility. You don't necessarily need to commit for the long haul but you also want Once you finish a program for a month or 12 month, you become what remote year refers to as a citizen. And one of the big benefits of being a citizen is that you can basically drop into any other program, you could join an entire program you could drop in for a month, when I was in Cape Town in March, I just dropped in on another program had access to, you know, 30 other people that, you know, we're all doing the same thing. So it's easy to jump into that community, to make new friends to have people grinding with you, late night in the office, trying to think of what else What didn't I cover?
Oh, no, that that's all awesome and really informative. I so is it a hard requirement that you'd have to have a job or some kind of work to do remote year or could you be unemployed do it?
I'm not big on their admissions team. I don't want to commit to a firm answer. What I would say is yes, it is fairly strict, but If you are pursuing, like to say unemployment is isn't a great like, say you're pursuing a passion project, say you're trying to build a business or you're trying to build a blog, or an e commerce business or a drop shipping business or whatever, I think I think they'd have no problem accepting you. Like, at the end of the day, you got to be able to meet the expense requirements, you got to be able to pay for the program. But if you're grinding, if you're, if you're working on your MBA, or if you're working on a passion project, I don't think they'd have any problem with that. My fallback plan if my consulting business never actually got any clients was to learn to code so you know, I think they would have been okay with that. It's ironic that that came full circle and I ended up deciding to do it after the program. But --
Yeah, that's I was just curious. I was just curious, like, if everyone was kindness, similar jobs, but full time Remote Jobs or even mentioned freelancers Yeah, that makes sense. Like someone could also be, I could totally see especially the four month program like taking a sabbatical from like a really stressful job. Maybe you were like, an exact level at a startup or I don't know some other kind of really demanding finance job and you just want to take a break and maybe you're pursuing other interests, but you're not, you know, working full time or really bringing in a strong income, but maybe you've money saved or something from your previous stressful job, but any event Um, so that's really awesome. Okay, so you did this 12 month program. It sounds like he went to more than 12 countries, though. In 12 months, it sounds like you went to a bunch of and listed them all out.
So the list was actually just 12. I think I took a tally at one point. I think I hit 20 countries, took 60 flights Exactly. And visited five separate continents. And one of the unexpected benefits of this program that I did not appreciate or anticipate is that living in a month Living for a month in a faraway city also gives you a jumping off point to get to so many other places in the world. So, you know, if you're in Thailand, it's very easy to fly to Bangkok to fly to Vietnam. You know, you can just bounce around, we call them side trips. But, you know, when we were in Malaysia, we went over to the island of Borneo, which is actually technically still Malaysia. But, you know, it's easy. It's a two hour flight to get to some of these places that when you're living in New York City, you wouldn't necessarily go out of your way to visit. So it allows you to hit a lot of different countries. Some are just flybys. Unfortunately, it's not necessarily a full month experience. But you know, that's one other benefit.
Nice. So switching gears a little bit, but I'm curious what is your work schedule look like while you were doing remote year? So you mentioned they give you the infrastructure, they give you resources so that you could work remotely co working spaces and whatnot. And you mentioned Like, what you were doing at this time consulting mostly for you know, a single company. Were you working like a normal full time day? game? Just curious what that looked like.
Yeah, it? It's an interesting question and it definitely varies per person. I was super fortunate that all of my work was directly for basically one of my best friends from high school. So my lifestyle was pretty flexible. You know, what, if I reached out to him and let him know I needed Thursday, Friday off to go take one of these side trips, he was super accommodating for that. I would say the other side of the coin, you know, when we were in Southeast Asia, so Kuala Lumpur, for example, is an exactly 12 hour time difference from New York City and there were people that were working East Coast time so they would get into the office at 9pm and they'd be walking home at you know, 3am for a. So So lifestyle can be can be tough. If you have a strict working hours schedule, if you need to be some people got around that a little more creatively by being online for half the day with their employer. They knew sometimes they'd have to have meetings and communicate directly with their team. But their team was willing to accommodate the fact that they were in a totally different time zones.
So maybe you overlap for three or four hours a day. For me, it was very much project based. So as long as you got projects done, and you got them done on time, and they were done well, my, my, my friend Mark didn't didn't mind what I was doing. I would say there is it's kind of like one of these cliches that people talk about working remotely, but they say, you know, you can get done between the hours of like 9am and two or 3pm what you would normally get done from 9am to like 630 or seven back home and I I actually do think that's true. I think there's a lot of wasted time. Back in the States, people browsing the internet standing around the watercooler taking a long lunch. If you're in Barcelona, Spain, you know you don't want to be wasting that time in the office so if nobody's if there's no FaceTime and nobody's watching, if if you know the results are the only thing that matters, you know you'll rush through that launch and you'll rush to not rush in a bad way obviously you need to do your job well and produce high quality work but you know, you don't waste time around the office because you want to get out there and explore the city and do fun things. So you know, I do think the amount of time spent in the office is reduced I wouldn't say the output is is all that reduced.
So the lifestyle is kind of what you make it you just got to get it done. You got to work it out with with the people you answer to. If you're a freelancer, it's very much eat what you kill. So you know, our month in Thailand was was easy to just hang out on the beach and not get a lot of work done. That's really tough for somebody with With a more structured, you know more quote unquote corporate job. It's also tough for a freelancer because they don't have any cash coming in. So it really varies. It depends on you depends on your background.
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Did you decide which countries you got to go to or was there kind of like this set itinerary that they gave you?
My program was a set itinerary at the time. That's the only way remote your did it. They only had they'd have one program launching maybe every couple months. These days they've scaled up quite a bit such that they have some of these itineraries planned out. You know, months in advance, the four months in general, I think they're actually continent specific. So if you knew you wanted to do Southeast Asia, you could purposely target a four month program that that does Southeast Asia. So you definitely have more control now over over what your itinerary is, but you can't, you don't piece together, you know, one month at a time. It is one cohesive group. So my group which started with 73 people all traveled together, which we won't even talk about the nightmare that is,
I just wanted I was also are you with the same like group of people for one whole year or because I'll say I traveled with my best friend once for a couple weeks in Europe. We were We were 19 and I noticed his preschool like she's like a sister to me, but we almost killed each other trip. I mean, maybe now if we did it, you know, being much more older and wiser we wouldn't but oh my god, I swear that it was like yeah, anyway, but..
It's like family, you love them, but you don't have to give them Along with them.
So you're with the same 73 people for 12 months.
Yes. We didn't end with 73. But in theory.
Okay, so I was because I was also going to I was also going to ask if, if like, so Okay, so logistically, so there's 73 of you, they're giving you apartments, how many people are living in apartment? Do you all live in the same complex together? Like?
Yes. So that's another thing that that there so one, it varies between city to it's, it's changed a bit over time. So, you know, when I went through the program, in a couple cities you've had, you'll have a couple sporadic like private apartments. Otherwise, it's largely like two bedrooms, maybe three bedrooms that you're sharing with other people on your program. In some cities, it actually is all in the same building. Like in Buenos Aires, we were all in this beautiful I think it was like a former hotel that they converted to. I don't even know what they use it for on it. day to day basis. But we all had like great private suites, there was a gym on the roof, an area for us all to hang out. So being in the same buildings was really awesome. They're trying to do that a little bit more where they can today.
There are some countries that just aren't aren't set up like that. Where it's a little bit harder to get everybody in the same building. They don't really have like large high rises where that's possible. The Most Extreme living situation not extreme. It was a lot of fun. But in Lisbon, we actually had an apartment with I think, 14 people that I lived in and below it was a half floor. So we had the entire floor below. It was another half floor that had seven people. Everybody had individual rooms in that in these. And then there was like a half floor common space as well. I think it was basically a hostel that we like took over the whole place. So it's super varied, depending on your personality, like they'll try to try to work with you. If you really, really need or want private room. They'll try to work it out. I'm somebody that doesn't mind being around a Lot of people doesn't mind roommates. So, you know, I raised my hand for the 14 or so it depends.
Yeah, I was I was thinking as you're saying that I think it would really vary on on the person. Like, yeah, how much interaction living in a 14 person apartment? I mean, I when you say that I'm like getting like chills I'm like, oh, like one of those you know this reality shows when I put you in like a tough situation intentionally or something but take yourself like glib with these, you can't leave the house with 14 people know. Exactly. But if Do you think it's possible, though, for a person on their own, like not as part of this group to plan a similar trip?
Or did you find because I know like, well, anyone could go to all these countries that you listed, right? Like we could take the list. We could just go there. We could spend each one. But how like, impactful I guess where the resources that you had in each country and this network of people and you mentioned I forget the name, but you said Like the city, the city people or the city, the people actually live there. How much did that impact your trip? Or your time abroad? Yeah.
Yeah. For me personally, it was huge. Like, you can absolutely replicate this trip, you can do it for a lot cheaper. And you know, some people made that decision and decided to leave the program because they could do it cheaper. I personally found a ton of value. So from the from the resources perspective, the program has to program leaders who actually travel with you all year. So we had two awesome individuals Westie and Alexandra, who started with us on day one, they were at the airport day one until day 364 365 or whatever the the Saturday at the end was, who were there for everything from you know, operations, organizing our buses, our shuttles, our apartments, to programming. So those guys are huge like they we called them mom and dad like they very much were and then when you landing a city. You've also got to city people, one who's focused on operations, making sure the apartments are set up when you get there.
Any challenges associated with that you've got a experienced manager whose sole job is to try and find unique opportunities that you might not otherwise be able to take advantage of as an individual. So, like I said, the city team is huge. Like when I lost my passport in Malaysia, I had absolutely no idea what to do. I didn't speak the language. You know, it was it was a public holiday, I had to go to immigration, I had to get exit stamps to prove that I actually entered the country legally if I didn't have somebody there. This all happened on a Sunday. And on Saturday, I was supposed to be in Philadelphia for my sister's wedding to actually officiate it. Without them like I wouldn't have made that wedding from an experienced side. They also provide a lot of really unique experiences. Take March, for example, I was I was in Cape Town, and they organized kind of a speaker lunch. And the speaker was this guy named Christo brand who is actually the main Warden for Nelson Mandela throughout his stay in prison. And when Mandela got out and was in charge of the country, he actually, he became friends with Christo throughout his stay.
But when he got out, he actually employed him on the team that was drafting the new constitution for South Africa. So this guy is just seeing, like, Mandela's entire life, became a great friend of his and we had the opportunity to meet him, to hear him speak, and to get signed copies of his book, like that's something you would never be able to pull off as an individual in when I was in Buenos irace. You know, when you go to ba I don't know if you've ever been there or not, but There's this tiny colorful little street area, it's this little neighborhood called La Boca. And every tourist that goes through ba will see it, you've seen pictures of it, you see an Instagram of it. And I'm drawing a blank on the name of, of this island. I want to say it's Islam ICL, but just across the river there's this extremely poor neighborhood. That's just seeing none of the benefit that la boca did. And the town came together and as a as a campaign to try and bring more awareness to the town.
More assistance to the town they started putting up all these beautiful murals and and painting these buildings, different colors and things like that. And that's that's a part of town that that unless you know somebody unless you know a local, you might not necessarily even want to walk around in like Uber's might question dropping you off there. But because we had a city team that was in touch with people that actually were in leadership positions within In the town, you know, they welcomed us in. And we did like a little street barbecue. And they took us around the town and showed us all of the street art and the murals. You know. So that's just another example of things you really wouldn't be able to pull off on your own.
Yeah, that makes a ton of sense. And sounds like some really amazing experiences and talks and events, you got to go to that, as you said, you would never be able to coordinate on your own. If you did just the time it would take. It would take so much time and effort and planning and you have to work and it's just like, way too much for an individual to do. But looking into the future, like do you see yourself working remotely again? Whether it's for a short period of time or a long period of time? Is that something you want to keep doing?
Yeah, that's, that's my ultimate goal. You know, honestly, that was that was the real driving factor between the switch to software engineering. I do want to be remote. I recognize the fact that I don't necessarily have the experience. It's necessary at this point to really try and do that today. So my goal is to spend probably a couple years one to three years in an office, you know, getting mentored by more senior developers building my skill set further working on some real projects to add to the portfolio and then to try and set out and find something remote and and really go remote full time. Whether or not I would be on the road for a full year at a time.
That's probably not. I mean, traveling for a month at a time is exhausting people. A lot of people looked at remote Yeah, as kind of being a vacation and you know, hopefully your vacations are relaxing these days. I don't even know if people have relaxing one week vacations, but you know, by the end of those 12 months, we were exhausted we I don't want to say we were ready for it to end but we just needed a break. So I think my perfect balance would be Maybe three to six months traveling, and then the same back home the flexibility to get back home for holidays, stuff like that. But yeah, the goal, the goal is definitely to to set out and be able to travel again.
Oh, man, I have like so many other questions. Don't ask about that. But that I think that sounds like a really solid plan like working, you know, 123 years and in office, finding a remote position and then traveling, having the flexibility to travel not necessarily be on the road the whole time I traveled. The last time I did any long term travel. This was like, I don't even know like, five, six years ago at this point. I traveled for three months straight and Southeast Asia. I had spent other time living overseas, but I wasn't like traveling like I was in Thailand, for instance for nine months. And that's like very different from moving around every couple days. And I absolutely loved my trip when I was three months and I did this by myself. So I'm like kind of the opposite. Have you like I think I would kill those people like I love my alone time. Like, I don't mind eating alone I don't mind. I mean it's not great like eating alone like yet eating all your meals alone kind of sucks, but it doesn't really bother me I think that much. And same with living alone like I love to live alone, I love to be in my own room or whatever. Um, anything
Outside of that not to not to jump in. But like remote your isn't. It's not necessarily like summer camp like you don't have to be anywhere when anybody tells you to. So we definitely had people that that were you know, more either required time to themselves to recharge or like popped into a coffee shop instead of working at the CO working space. Like you can definitely escape the group.
Yeah. Oh, yeah. Yeah, I mean, yeah, that's good. It's comparison. Like it's not like summer camp for you. It's like a counselor and you have to be at certain if Yeah, if you're an adult, like you can kind of do your own thing. Go on your own trips, go work on your work on your own projects, or were at a coffee shop or something. But Oh, I love the three month trip, but it was even just three months, it felt really long. And I remember like, yeah, it just feels like a lot of work. And I felt like, I mean, I guess if you're staying in one country for each for a month, that's a decent amount of time. Like I was staying places for a couple days or a week at most at a time. I felt like I was able to get work done. But I wasn't super productive. I wasn't super efficient, like because of all like the I think the overload of just like traveling so much in trains and buses and blah, blah, blah. That I wasn't like super, super efficient. Yeah, I don't know. But I cannot I also know that as you say, like some people you feel like you get more done in less hours because you were wanting to, you know, go go out and travel so maybe it's different for --
But I mean, at the end of the day like FOMO is real too, right. So like you You don't want to be cooped up in the office while while your friends are, you know, hiking a volcano or something. So yeah, no, I, I definitely get it.
Yeah, yeah. So I want to ask you one question like, what advice could you share with others that are listening who want to do something similar whether it's through a program or not, but they want to have the flexibility to travel while working?
Sure. And I'm probably gonna list off a bunch of like contradictory things that I didn't necessarily do any of. I guess, looking back on it today, I'd sit down and think like a little bit more about, about why you want to do it. It was interesting to be with a group of, you know, 70 other people for a whole year because a lot of people came in kind of saying, you know, I didn't really have a reason to do it. It just looked interesting. So I'm here, but the more you spend time with them, and the more even they kind of figure it out themselves, why they did it. You know, everybody kind of had a reason. In some ways I you know, I think my reason was just running away from from this toxic lifestyle. Like when I entered remote here I looked at as, you know, life was great. I don't have any reason for doing this, like I was working in private equity as making tons of money. But then I got on this trip and I realized, yeah, but you are miserable like you are running away from a horrible lifestyle, you know, mentally physically unhealthy lifestyle.
So, you know, are you doing it to run away from something? Are you just somebody that craves flexibility that constantly needs change that you know, is just looking for some more stimulation looking for a challenge. You know, that might guide your reasoning as to whether or not say a program like remote your makes sense going off on your own makes sense or whether or not you'd even be successful. I would say ease into it, which clearly isn't something I did. You know, I just kind of quit and went But there are easy ways to to see whether this lifestyle might work for you like you don't have to commit to a full year. You know, maybe you just request a remote day, from your employer a day here and there and go work from a random coffee shop, like somewhere in Manhattan or something, you know, see how hard it is to interact with your team and get your job done as kind of like a trial run, you know, even request like a week away, or offer to like one of the things I've thought about doing is, you know, you've already got a seven day vacation scheduled somewhere like as to take 10 days and offer to work three of those remotely and just see how it goes. Because at the end of the day, even when you need to go pitch this to your employer, you've got to be able to prove that you'll still be successful from afar.
So, you know, if you have any of these examples of doing some of this work already, from a laptop from a cafe, you know, it can only be to your benefit for actually being able to successfully make that switch. And I'd say like the final one might just be that like, a lot of people will look at your Instagram or your Facebook, and it'll look like this like most beautiful, glorious vacation. You know you're hiking, you're you're eating all this amazing food you're on these beautiful beaches. But that like that is a super filtered Instagram a view of long term travel. Like a lot of things go wrong. Like I lost a passport. We had two guys on the trip get Dengue fever and Thailand. You know, people lost family members. I didn't have the cash to necessarily fly home to attend the funeral. Like, it can be a roller coaster. It really is taxing on you. You know, you could lose a job. We had one poor girl who had a freelance client who just never sent that So she ended up having to drop out of the program because this expected income stream just never came in. So I'd say be ready for the roller coaster. Don't expect it to be sunshine and daisies.
Wow. Thanks for all that advice. And I feel like it just yeah, I feel like it's so contradictory because I feel like sometimes to do something like this or to go travel for a year, whether it's on your own or through a program, you need to kind of just like do it like, like, I feel like you can almost get too stuck in the planning, they will never sure you, but then contradictory. You also want to make sure you have like maybe a financial cushion or something. So if one of these unexpected things happen, like the missing check you referenced or a family member passing away, or getting some kind of illness that you had to financial security where you can, like cover those unexpected expenses. So I think it's a weird balance of like planning but not planning too much. Because I totally agree. Yeah, cuz I Like when you said like, I just kind of quit my job and went for it. In my head. I'm like, Well, you know, like, that's probably what you had to do at that time. Because if you thought too much or strategize you maybe never would have gone the trip and then you wouldn't be where you are today, you know?
Yeah, no, I, I totally agree. It's, it's a, it's one of those things, you could get caught up in analysis, paralysis and just never make the decision. So sometimes it is important to just jump. But, but having a backup plan, having a way out is definitely important as well. I think one of the biggest benefits of traveling long term is that so much does go wrong. You start to build this ability to just remain kind of flexible, and and to not get too stressed out when things go wrong, because you start to put in some into place some of those things that that do give you a way out.
Awesome, Dave. Well, I really enjoyed chatting with you. Thanks again for coming on the show and where can people find you online?
Yeah, I've got a website, davetrabka.com. And all of My handles across social media are pretty much Dave Trabka, @davetrabka, so any of those mediums work. I'm super, super responsive.
Awesome. Well, thank you again for coming on.
Yeah, of course. Thanks for having me.
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This episode was transcribed with the help of an AI transcription tool. Please forgive any typos.
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Dave’s Remote Year Reflections
Listen to the episode to hear Dave’s full story. Here’s the short version!
The first step to any big life decision is mental, and it was no different for Dave. “I came to a stopping point where I just kind of self-internalized and asked the question, is this what I want to do with the rest of my life? And it was a really quick answer that, no, it was not. So I decided to explore what other opportunities might be a good fit for me.”
“After a few months of toiling with the self-learning, I ended up deciding to go to a bootcamp. I really wanted to accelerate things, be in more of a community, and have the support of instructors. I wanted somebody to lay out some of these project ideas and help me build a portfolio. So in February of 2018, I applied and was accepted to Fullstack Academy of Code here in New York.”
Discovering Remote Year: What Is It?
“Fundamentally, Remote Year was started as a program that you would join with anywhere from 50 to 75 other people,” Dave explains. “You come in with a job that you can take remotely—Remote Year does not provide you with a job. You either negotiate with your employer to go remote, maybe you’re a freelancer, so you kind of control your own destiny, things like that.”
Even though it doesn’t come with a built-in job, using a program like this has several advantages. “Remote Year provides infrastructure and logistical planning to allow you to live in any given country for a month at a time, with an apartment, access to a coworking space, events in the different cities, and local connections to help out.”
Once you’ve finished a program (currently they offer 4 or 12 months), you become a “citizen” of Remote Year. Dave explains, “The big benefit of being a citizen is that you can basically drop into any other program. You could join an entire program, or you could drop in for a month. When I was in Cape Town in March, I just dropped in on another program and had access to 30 other people that were all doing the same thing. It makes it easy to jump into that community, make new friends, and have people grinding with you late at night in the office.”
Advice for a Remote Year
First of all, Dave advises, “Ease into it. There are easy ways to see whether this lifestyle might work for you. You don’t have to commit to a full year right away. Maybe you just request a remote day or week from your employer here and there and go work from a random coffee shop. See how hard it is to interact with your team and get your job done as kind of a trial run.”
The other important thing to know? “Be ready for the roller coaster. Don’t expect it to be sunshine and daisies. I lost a passport, we had two guys get dengue fever in Thailand, people lost family members and didn’t have the cash to fly home to attend the funeral. We had one poor girl who had a freelance client who just never sent the check. So she ended up having to drop out of the program, because this expected income stream just never came in.”
You won’t usually see these difficult parts of being a digital nomad on Instagram, but the takeaway is that you should always have a backup plan. If you’re a freelancer, it’s best if you have multiple clients so you’re not reliant on one. If you’re working a remote job, think about what you’d do if a layoff happened. Either way, have a financial buffer to protect you from any emergencies that arise. It’ll take away that potential stress so you can focus on enjoying your time exploring a new country.
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