Katherine Conaway / Digital Nomad Survival Guide

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Jonathan Okay. I’m happy to sit down remotely here and talk with Katherine Conaway, who is on the entire other side of the world, and so this is just the amazingness of the internet in action here. So, how are you doing, Katherine?

Katherine I’m great.

Jonathan She’s the author of the Digital Nomad Survival Guide, which was recently released and published. And, as we’ve talked about on this show, being a digital nomad requires travel and working, and this guide is really comprehensive. But before we go into that part of the interview, I want to talk a little bit about your background. One of the interesting things I learned in the bio from the book was that you originally we a math major and switched to art history, which you don’t hear very often.

Katherine Yes.

Jonathan So, why don’t you tell us about that?

Katherine Yeah. So, my dad... I guess this is where it starts, is my dad is very much a numbers and math guy. He’s a self-taught architectural designer. So, he was always doing geometry and algebra with me and making me help him with his company accounting. So, by the time I graduated high school, I had done calculus, multivariable calculus. I loved it. I did really well with it. So, when I went into college, I thought, kind of from the pressure to have a good major for a job and also because I loved math, that that’s what I would study. And I ended up going to Williams College, which is a really great liberal arts school that I had never heard of before I started applying to colleges. And when I got there, I was studying math, and it was going pretty well. I was in a linear algebra tutorial my freshman fall, which is like a four-person class with a professor and you’re presenting proofs and theorems.

Jonathan Oh my goodness.

Katherine Yeah. So, within the first two or three semesters of college and my math major, because I was already so advanced, I had no more numbers left. And so, my sophomore fall, I was in abstract algebra, and I’d go to class and I’d be fine, and then I’d go home to write my theorems and just be utterly lost, because there’s no calculation done. It’s just proving the existence of really abstract ideas. But at the same time, I was taking Introduction to Art History, which is a two-semester course. The first semester is architecture and sculpture and the second is painting, and everyone at Williams takes it because the Williams faculty and their graduates are known in the niche market as the art mafia, because essentially, so many graduates from Williams go on to run art museums. And so, there’s this incredibly weird peer pressure at Williams to take art history.

And so, I was this freshman in college and everyone’s like, "Well, are you in art history?" And I was like, "Of course not. I’m from Texas. What are you talking about?" [Laughs] But everybody else was, and so I was like, oh my goodness, I’d better get in art history. So, sophomore fall, I’m taking abstract algebra and crying because I miss numbers, and meanwhile, I’m taking art history with Professor E.J. Johnson, who’s this incredible architecture professor. And he’s an older gentleman and he comes into class with his Irish setter, who just sits at his feet, and he just tells the most beautiful stories about buildings and what they mean and how they told stories to the people that interacted with them, and I was just hooked. And so, when I decided I didn’t want to do the math major, it was like, well, what else am I going to do at a liberal arts college? Why not this incredible major?

Jonathan That’s a cool story. I started out a visual communication design major, which is basically graphic design, and then sophomore year, I switched over to computer science. So, I kind of went the other way, but I loved my intro to art classes.

Katherine It gets so much hate, but it’s actually an incredibly useful thing to learn. Like, you look at visual stuff... Especially now, you look at visual stuff every single day. Like, what is Instagram?

Jonathan Yeah. Exactly. [Laughs] I wish I had paid a little bit more attention. I know just enough, but yeah... So, I jumped over to the computer science side of things. So, drawing a connection from that art history, and now that you are traveling the world, in some way, is that kind of preparation for what happened unintentionally?

Katherine I think so. I never had--I still kind of don’t have--a specific career ambition. And so, in college, in those art history classes, you’re studying primarily Western art, but you do have to take some non-Western courses, which meant I also studied Buddhist art and some other cultures with that. And so, that paired with studying abroad in Italy really made me interested in the stories and the people around the world, and when I was graduating college, I didn’t know what I wanted to do and where I wanted to be in life. So, I just said, "Well, what would be interesting?" And that turned out to be I’ll go teach abroad.

And once I started living abroad, I just kind of really got sucked into it, and even though I moved back to the States for several years and did some other jobs that led me to the work that I do now, I still just...one of my biggest priorities, if not my biggest priority, has been to have interesting experiences, to learn about other people, to hear the stories that other people in other places have to tell. And I think that that is what art history is; it’s just not billed that way.

Jonathan Yeah. So, I’ve read the book, so I did a kind of cheat here, compared to our listeners here. But so, you graduated college, you had a couple jobs. I believe one of them was in New York. And your kind of transition into being a digital nomad was not an intentional thing. You didn’t set out to say, "I’m going to travel the world consistently all the time." How did that kind of play out?

Katherine Yeah. It was definitely not intentional, but I guess I kind of set myself up for it without realizing that it was going to come together. So, I was working in Brooklyn at a design studio and production, which meant organizing these projects we did for our clients that were digital insulations or video shoots or whatever. And at the same time, my mom and stepdad sold our house and bought a boat and were going to go on this crazy boat trip. And I was kind of like, I don’t know what my career is, so I’m going to take a few months away from the city. So, I decided I’m going to leave my job, I’m going to put myself into storage, I’m going to take four to six months away, visit my parents, visit my friends and family, and then I’ll come back and focus on the next step professionally – as one does. [Laughs] I don’t know how I saved the money. Like, I am the most crazy... That is what I will say is the actual secret, is that I, since I was 18, have tracked every dollar I’ve earned and spent in a spreadsheet, and so I am able to do things that don’t make sense in terms of living in New York on no money and saving something. And I don’t put that in a savings account. I travel.

But anyway, so I kind of set this stuff up, and I was leaving my job, and I just told all the creatives and all the producers that I knew, "I’m going to come back to New York in the fall, and if you could hook me up potentially with some freelance gigs, please keep me in mind." And I just started telling everybody, and I think that that’s a really good lesson, because I wasn’t hard-pressed, like, I need a job tomorrow. It was just like, "Hey, we’ve worked together. I like you. You know my skills. Please just remember that I’m a person on the table." And it made it not like a creepy, "hire me" vibe. And one of the creative directors that I knew had moved from the city and started her own little studio working directly with online entrepreneurs and small business owners, and she remembered me mentioning it at some point and reached out pretty much exactly a month or two before I left my job and said, "Hey, I would love a little bit of production help. Could you do four or five hours a week?" It’s like, yeah, that sounds great. And so, by default, it was a remote job, because she was in D.C. and I was traveling. We already knew that.

And so much of production is just remote already, even though you don’t think of it that way, because when you’re managing a creative project with clients, they’re not in the office with you, so you’re already emailing them updates and coordinating that and sending invoices online and receiving payments in various methods. And so, it’s something you don’t think is remote but it actually...if you’re working with a client these days, you’re doing a remote job, in terms of the process and the tools and the video calls to do check-ins when you don’t need to have ten people in person.

Jonathan Yeah.

Katherine So, yeah. So, that came along and it worked really well because I knew her and I liked her and I liked what she was doing and she needed the skills that I had, and it was just enough money to keep booking three to eight weeks at a time. And I just said I’ll do this as long as I can, and I’m coming up on my three-year mark of that. [Laughs]

Jonathan Oh my goodness. So, really, the key theme was that you had enough professional experience before doing this and enough contacts and networking that you weren’t trying to launch a new career and travel the world at the same time.

Katherine Yeah. And I think that a lot of people are like, "Oh, how am I going to just get a job?" And sometimes I think if this whole thing fell apart... And honestly, I was with her up until very recently, like, the past two months, and then she kind of wanted to move away from projects with deliverables, which gets rid of your need for a producer. And so, now I’m working with a client that I originally started with through her. So, I haven’t had to actually go out and cold turkey get a new job or a brand new client.

So, I kind of try to think if I’m giving somebody advice, how would I do this again if I had to go get a new job tomorrow? And it’s very tempting to apply to jobs. Like, a couple of times, I’ve been stressed and I’ve applied to two or three jobs with a cover letter, and it’s always nothing. And before I got my job in New York, I applied to 100 jobs when I was living in Austin and I got nothing. And then somebody on LinkedIn from my college posted a thing about a friend’s company, and I immediately got set up for an interview, and that’s what got me the job that I moved to New York for. And I think that I don’t know if it’s so much about...

I mean, yeah, there are job boards with remote jobs, and I’m sure you can get those jobs, but I think what’s more likely to pay off, especially with all the statistics about, like, 85% of jobs are through your network, is to not say, like, "What job do I want?" but really know the skills that you have and the things that you want to do and the way that you can do those things, and then just start talking to a lot of people about that. And eventually, somebody’s going to say, "Oh my God, you know my friend Sarah really needs help with that. Do you think you could do something?" And then you hop on a call with that person and you talk through what they need, and probably, you can find some kind of agreement to get started And if you’re willing to take part-time freelance gigs, I think you can step into something.

Jonathan That’s really true, and a similar experience has really been my journey. I mentioned in a previous episode that all of my current contracts and opportunities and things that I work on came through my network, and either referrals or repeat clients that I worked with before. But the first year to year and a half starting out as freelancing, it was a big hustle to get that initial group. But now, it has pretty consistently kept me employed. I’ve never been without an opportunity to work on, which I’m very grateful for. But it is. My experience of cold applying to jobs was similar to yours, where even where I look it and I’m like, "Man, I’m perfect for this job!"

Katherine Yeah.

Jonathan And I write an interesting cover letter and you do all the song and dance, and you get a reply back, "Thank you. The position’s been filled."

Katherine If you get a reply.

Jonathan And you’re like, oh, they knew someone locally! Or it was their friend! They just had to post it to meet some requirement or something.

Katherine Well, that’s why I think, like, now I’ve kind of taken to writing blog posts or putting something out there that more than that one person could read, because I don’t know... So far, nothing’s come from it, but maybe it could. And also, I don’t know, I do a lot of stuff, not unpaid work, but, like, if I think something’s interesting, I’ll just each out to somebody and talk to them about it. Or if somebody’s interested in what I’m doing, I’ll have a phone call, but just because...I feel like the more I talk to different people, interesting things can come of that. And it might be ten years from now, but I want to set up those opportunities.

Jonathan Yeah. Yeah, that’s a big aspect of networking. And you said approaching people about, "Hey, this is what I’m looking for," without any type of sales pitch for, "Hey, give me a job."

Katherine Yeah.

Jonathan So, what is it that you’re currently doing, work-wise, and experiencing the types of projects and such that you’re working on?

Katherine So, like I said, I was working with this woman, Sarah Ancalmo, who the company that we were basically the two of us was Public Persona. So, for about two and a half years with her, she was the creative and the founder, and I was the producer/other half, and it was brand strategy with these online entrepreneurs and small business owners. And so, they were already pretty successful, but it was redefining their brand and where they were trying to go and how they wanted to be online and imagery, and then often executing that by doing photo shoots and logos and websites. And so, my job was just kind of keeping track of all the different clients and where they were and who was responsible for what.

And through that, I also started doing more organizing the content or writing the copy for the website or helping on the design work, where Sarah would set up an InDesign file, and then I would make 50 pages of something out of a Word document that the client sent. And so, I got a little bit more involved with writing and design, but always kind of just under what she was doing. And I’d also done some market research at a couple other jobs and internships in the past, and so I pretty much was just like, any time we looked at what we were doing with a client, I would just take on the hats that weren’t the super, super creative high-level thing that Sarah was doing, or really, design skill, and I would just do that.

And then in last summer, 2016, a client came to us, called Bluffworks. The client was Stefan. My friend is Stefan--he is Stefan. And he had this men’s clothing company that did travel clothes that are meant to look good, instead of the dweeby knee zipper-type cargo shorts.

Jonathan Yeah.

Katherine And so, he’d been successful and he’d done a couple kickstarters, and then he was getting ready to launch this new blazer that they’d created that was like, oh, this great blazer. It looks like a real blazer and not some cotton, lumpy thing, but it can actually travel well and you can wash it in a washing machine. So, he came to Sarah to get her art direction for their Kickstarter shoot, and so I worked on that remotely over the summer and the fall, and we launched the Kickstarter and it did really well. And then he was like, okay, so we’ve done this big step of the process, and now we’re ramping up to launch it, which is happening this month, like fully on their online website or shop. And in that interim and moving forward, it’s about finding bloggers who would be interested in that, travel bloggers or business travelers or whoever might want this special blazer or pants, and PR and media. So, my job now part-time is with him, doing that kind of research, setting up our database of those people tracking the progress, and helping organize them getting the products, and also them doing a review or them writing their article or whatever that is, and making sure they have all the information, which is all just something I’m making up with him as we go.

Jonathan Excellent. So, you really have an established routine and client that you’re working with. How has that freed you up to travel, and what are some of the places that you’ve been over the past three years?

Katherine Well, I wish I had an established routine, but I kind of have an established way that I check in with work. But it has allowed me to travel because... I think the way people talk about it now is, like, asynchronous work, which is the things that you can do not at the same time as other people. And actually, even in production, there’s very little that has to be done at the same time. If we can overlap for an hour a day on Slack to talk about client stuff, or schedule one call a week, there’s not a lot of time otherwise that we actually need to be on board. And as much as people sometimes expect an email back immediately, usually, if you set an expectation up front, I’ll get back to you within 24 to 48 hours... And I always really try to do a good job of summarizing everything that I’m reading into really clear-cut emails with numbered items, or a breakdown and a bold question, like, "What do you want now?" It ends up really not being that much of a problem for the people I’m working with or our clients.

And then where I’ve traveled to... The first six months was, like, a crazy itinerary all over the U.S., and some time on my parents’ boat, which was really cool. And I went with them from Chicago to St. Louis and then I went somewhere else, and then I met up with them in Chattanooga, Tennessee, and we went out on the Tombigbee, down to the Gulf, across to the Panama City armpit of Florida area. And then I met up with them again in the Keys. So, that was really cool.

Jonathan Oh, man.

Katherine Yeah. It’s called the Great Loop. It’s this thing that nobody’s heard of, but 100 retirees do every year, and it’s really, really neat, and I wish that I had a boat. But I’m close to that. So, people are like, "How can you go on a boat for three weeks at a time with your parents?" And I’m like, "I don’t know. It’s fine. We just... I don’t know. It’s great."

Jonathan That’s awesome.

Katherine Yeah. It’s actually been really cool to get to know my parents as mutually adult people. And that was still when I was very much in the early stages of figuring out how much work I had, how much money I have, what this really was going to be. And once I realized that I might have enough to really travel and not just visit people, that’s when I started going abroad. And so, I went to Dubai, also, to visit friends, and then I went through Iceland on the way back. And that was my first complete by myself, booked an Airbnb, didn’t know a single person in the country five-day trip in Iceland, which was amazing. And I got so lucky. I got to see the Northern Lights, and they had canceled every other night for weeks. I mean, it was such a great trip. And then I was like, okay, cool, I can do this for sure. So, I got back to the States, spent a couple months planning trips. I decided to apply to Julliard, so I did that, had an audition there, and didn’t get anything, and it was wonderful.

And then I was like, all right, I want to go Asia. I have heard some things. So, then I decided to do yoga teacher training in India, and I got my mom to go with me. So, we traveled. We did the four-week teacher training in India, and then we traveled in India and Thailand together, and then I did two more months alone in Southeast Asia.

Jonathan Oh my goodness.

Katherine Yeah, which was great, because it’s a really affordable place, and there’s tons of people traveling through it, so it’s, like, for better or worse, a really well-beaten path. And I think for a solo female traveler, it was somewhere that I could go and afford, for 20 to 40 dollars a night, I could get a private, clean hotel room where I felt safe with my computer and my life. And that was really important to me, to be able to say, like, "Oh, I can afford an $80 flight and I can afford a $20-a-night room and do this trip not at a backpacker level and feel confident about working and being by myself." But that’s when I decided to do Remote Year, because I realized that I didn’t want to have to plan all of that and I didn’t want to have to be alone all the time. And so, I went home for a few months in preparation for Remote Year, and then on January 30th of 2016, I flew to South America to start Remote Year, and so with that, the program did 12 countries in South America, Europe, and Southeast Asia, and then I did a couple extra side trips.

Jonathan So, with Remote Year, that’s like one of these programs that is really all-inclusive in terms of traveling, and you’re with a group of people that’s consistent. And do they handle all the logistics for you, so you can just kind of focus on being where you’re at and working? What’s that experience like?

Katherine Yeah. And one caveat I will say is I was in the second group of Remote Year, so that’s great. I was very interested in being in that beta group, because I suspected that it would really become popular and it would be very different in the future. So, when I started, which our group started in February 1st of 2016, I think they had ten total employees. We’re the second group. That’s 75 of us after the first 70 people that were in the first group. And it was very much like, by the seat of their pants. And like, oh, we’ll scout out a place, and then we show up and we’re like, "This place sucks." So, South America was a little bit of a rough ride, but over the course of the year, they’ve really grown as a company. In October, they got a Series A investment of $12 million, and I think two of the investors were a founder of Airbnb and a founder of WeWork, so people who really understand a lot of what Remote Year’s trying to do.

Jonathan Yeah.

Katherine And now they have over 100 employees, and they’re launching one program a month this year. So, my experience versus a future experience is very different in some ways, but the offer is Remote Year the company, you as a participant apply, and you get accepted and you join, and you’re going to be one of 50 to 75 people in this group. And that group will be together for the year. Each individual person will pay Remote Year 27,000 U.S. dollars over the course of that year through deposit of monthly fees. And Remote Year will be providing to you as their service and product the accommodation each month, the workspace membership this month, and that might be an existing workspace or one that they create or whatever. The accommodation could be a hotel, but usually, it’s increasingly now a private or shared apartment, shared only with other people in your group -- not strangers.

Jonathan Okay.

Katherine You always get your own room. You might share a bathroom, but it’s always like a one- to three-bedroom apartment typically with other remotes in a building.

Jonathan Okay.

Katherine And then, so accommodation, co-working, the travel between each country, and just staff support and events and setting up activities. So, some people here that number and they’re like, "That’s so expensive. I can do it cheaper." And I’m always like, you absolutely can go as cheap as your standards allow. However, what is the value of your time? Because I’ve been out of Remote Year now, again, for a month and a half, and I can tell you that today, I was throwing multiple fits, because I was in a cafe and the WiFi wasn’t working very well, and I was trying to research Airbnbs for Berlin, and yesterday, in the past week, I’ve been finding Airbnbs for Paris, and I’m stressing out about how much should it cost, what neighborhood should I go in, how much per night is reasonable in this country that I don’t know very well, and where am I going to work? What cafes? It’s exhausting. And I think that there’s this horrible decision fatigue that comes in when you’re trying to live this lifestyle, especially if you, as a digital nomad, plan on moving frequently. And if it saved me ten hours a week from having to research and plan every flight, every bus, every housing and activities, they set up activities and a co-working space, if that was just ten hours a week of my life, that’s very close to paying for the fees.

Jonathan Yes. Absolutely.

Katherine And I think people don’t value their time enough.

Jonathan They don’t. Or they don’t realize the value that is added to the experience of not having to worry about that, of all of the complexities... It’s complex enough running your own business and keeping your projects on track, but then to spend all your extracurricular time planning, and the logistics of that... There was a period in my career where I traveled a lot, but it was just domestically in the U.S., and even just booking my own flights and hotel and car and figuring out the public transportation system, it adds up.

Katherine Yeah. Nobody likes that.

Jonathan And decision fatigue is key. That’s what you’ve said. I absolutely resonate with that.

Katherine Yeah. And that’s not to say I think Remote Year’s perfect, or that it’s for everyone, and there are maybe other programs that are better for people, or maybe Remote Year’s not right. I think for me, it was good, because I had done it on my own, so I was able to appreciate what they were offering, and the fact that, yeah, not every housing is going to be my personal preference, but they’re trying to meet the needs of 50-plus people in this country, but they’re trying to do a good job. They’re trying to make their customers happy so they don’t have angry participants, which we’ve been through, it’s not fun for anyone. And they’re trying to have longevity, and they’re trying to optimize that many people in a city. So, they are trying to do a good job, and I think there are downsides with being in that group, and you’re definitely in a bubble, and it’s not necessarily the same...it’s definitely not the same experience you do doing it by yourself. But I don’t think that makes one better or worse, and I think I’m very glad that I had my own time before it, Remote Year, and now my own time continuing after it to compare and appreciate the different things that they have to offer.

Jonathan Yeah. So, talking about your book, I’m seeing a lot of the knowledge that we’re talking about here showing up in your book, and your book goes even a lot deeper. Just listening off some of the topics that you cover are finances, location scouting, housing, travel and transportation, jobs and working, technology, packing, and possessions, lifestyle, local culture, social and relationships. I mean, that is comprehensive to the experience, and I think that’s, reading through your book, that was one of the things that stuck out to me, was really how practical and how comprehensive it was. I made a note here as I went through it, and this is just my quote that I came up with, but to be successful, you have to be an expert decision-maker. And then you mentioned decision fatigue, and this book, I think, really addresses that head-on.

Katherine Yeah. Well, thank you, because those are exactly the words I want people to think. And I have to give so much credit to Peter Knudsen, which is how you’d pronounce it, you’d never believe it.

Jonathan Okay.

Katherine He’s from Minnesota, and it’s a Scandinavian name, so it’s Knudsen. He taught me that. [Laughs] But the book was his idea. So, we met on Remote Year, and everyone in my group... In future groups, a lot more people have connections to each other or to other remotes, because word of mouth is more of a thing. But in our group, it was 100% strangers, which was really interesting. So, Peter and I met in Montevideo, Uruguay, in February of 2016, and got to know each other a bit over the course of side trips and working and the random social interactions of Remote Year. And then he left the program, I think...I guess when we came to Asia. He didn’t want to be on it for Southeast Asia, so I guess he did the first seven or eight months with the group and then decided to travel on his own.

So, the ninth month, group was in KL. I was in Kuala Lumpur with the group, and he was in Bali, which is where I am now. And he sent me a message on Slack and said, like, "Hey, I have this project I want to talk to you about." "Okay, sure." So, we hop on a Slack call, and Peter is crazy smart. He does product consulting for video games. I don’t know what he does, but game theory and whatever.

Jonathan Okay.

Katherine So, in quitting Remote Year and doing this research, he joined all these Facebook groups. He was part of different digital nomad circles, and he was like, "You know, I keep seeing the same questions. I know there’s a ton of blog posts. I know there’s a ton of this information out there, but I’m still seeing a lot of people have the same questions. I’m still seeing a need not being met, and I want to write this book that’s not inspirational, not a laptop by the beach, but truly, how do you do this? If you said I’m a normal person with a normal job but I want to be a digital nomad now, how would you actually do that? I don’t think there’s an answer. So, he tells me this on the phone and I’m like, oh, genius idea, Peter. And I’m kind of, like, jealous and that. And then he says, "Well, you’re a writer, so I wanted to see what you thought of it and if you would help me write it." And I was like, "Hoo, okay." And really, that was great, because I’ve always wanted to be a writer and thought of myself as a writer, but I’ve had very limited official career title writing experience, outside of some random contract work.

But when I came on Remote Year, I was like, okay, here’s a great opportunity. I’m not going to blog as much about my personal experience, and I’m going to blog about...or write on Medium essays about the Remote Year experience, because I think there’s an audience for that, and it’s going to force me to write about something, but it’s going to focus me enough that I can wrangle myself. And it was really great because it was proof to me that if I put something out in the world, somebody else was going to see it and be like, "Oh, Katherine’s a writer. She writes about this already. She should write a book with me."

And so, yeah, we sat down and we had a kickoff call, and I wrote a really long case study on medium about exactly how we did this book, but I wanted to use my process from working with clients and the creative branding process that we did to make sure that this book had a very clear direction and the way that we were going to write it was really defined up front, which, I think, helped us, because we did it in three and a half months. The writing of it was in three months, basically.

Jonathan Wow.

Katherine So, I mean, that’s a very fast turnaround, considering we were both working and traveling and having social lives. And I think that that’s because up-front, we defined this is the voice we’re going to have, this is the content we’re going to have, this is which of us is going to do what thing first, this is the process we want to go from now to publish, and we didn’t have every detail planned, but I think we both brought a lot of our work experience and approach to the book. And even though it was a side project that we weren’t getting paid to do, we approached it the same way we would of a client job, most of the time.

Jonathan So, the actual production and writing and construction of this book was remote. So, you were kind of dog-fooding this concept.

Katherine Oh, we only saw each other twice while writing the book. We had an hour-long chat on an island in Thailand because he happened to be in town visiting, and we were like, "Hey, how’s it going? Let’s talk about it. Cool." And then we saw each other again in Ho Chi Minh City in Vietnam during the last couple weeks of Remote Year, because a bunch of people came back in town to celebrate together, and we met up with our illustrator, Lauren Hom, who’s this incredible letterer, who was also on our program. And so, the three of us met in a coffee shop to talk about getting ready to publish, and she showed us the final cover, and we were so excited. But the actual work of the book was done completely remotely through Slack, Slack calls, and Google Docs, basically.

Jonathan Wow. That is awesome. So, one of the questions I have is how do you balance your work and the cultural immersion that you’re dealing with in each place that you visit?

Katherine I mean, I think everybody does it differently, and I think you have to do it differently in every place you go, if you’re really going to diverse destinations. I’m in Bali right now, and first of all, I’m really not doing anything besides working and recovering from Remote Year and life, so admittedly, I’m not getting a lot of culture at the moment. But most of the time... When I’m in a bigger city, when I’m somewhere that has more infrastructure and a longer history or a better-documented history with an art history major and everything else, I go to museums, I make time to go to performances. And I mean, I don’t do a lot of research. I’ll just go to whatever. Like, I look up museums and I go to the top three or four that I see. And I look up theater or musical or dance and I just go to whatever they have, and I just assume that I’m going to spend somewhere between 10 and 30 dollars a ticket several times a month, and that’s just part of my budget for this, because if I’m not doing that, what’s the point of being there? And then cooking classes and eating a range of food, from street food to nicer restaurants, I think is important.

And then with Remote Year, that was great, because they would have networking events, and so I’d be able to meet people, or they would organize something where we could go to certain local businesses and maybe charities or other organizations, nonprofits, and talk to them about what they were doing or help in some way or donate money or whatever it was. Yeah, sometimes if you’re in somewhere that’s maybe less city, more rural, you’re not going to museums, but maybe you can... There are increasingly really interesting things. Like, in Southeast Asia, there’s this thing called Backstreet Academy, which is a way that you can sign up for a half-day class or activity and learn...

Like, I went and... I went to this woman’s...my age, probably, like, late twenties at the time woman, how wove scarves, and I just went to her house and her loom, and a high school kid came and picked me up in tuk-tuks. He was going to be my translator, because he was studying English in high school. So, he picked me up in a tuk-tuk that morning, and we went out to this random neighborhood, and this woman’s, like, concrete floor...no, dirt floor, metal-covered area where she and her mom had their looms, and I sat there and we just wove a scarf together. And she did at first and got it started, and then I sat down and she showed me how to do it, and I was bad and she laughed and I laughed. And at the end of it, I mean, I had paid a 15% deposit online, and then I paid here $20 in person, and the kid got a few dollars. So, it was under $30 for the whole thing, and it was, like, four hours. I got a scarf. I got to meet her and see her home, which was not very nice, but I think it’s important to know that if I was a twenty-something Laotian woman, that would be my life. And then when I’d go to the markets and I saw the scarves, and it’s like, they’re trying to get you to buy it for, like, eight dollars. You’re like, "No, two!" You’re like, oh my God, that was so much work. That is actually by hand. And then I don’t want to be a terrible tourist all the time, which is great.

Jonathan Yeah, but I think that definitely qualifies as a cultural immersion experience, for sure.

Katherine Yeah. So, I think you’ve got to look for those things. And increasingly with apps and stuff, there’s so many more ways of finding that. But there was a woman in our group was 65 in my Remote Year group, Carol, and she wasn’t working anymore, and so she would just walk around and talk to people. And every month we were like, "Carol, what are you doing this month?" She’d be like, "Oh, I’m volunteering in this person’s kitchen," or, "Oh, I’m helping at this elementary school," or, "I met this woman because I looked through the window and she was struggling to take care of children, and now I’m helping her babysit four days a week."

Jonathan Oh my goodness.

Katherine And because you’re in foreign countries, there’s just a lot less attention and regulation paid to things, and she’s 65 and doesn’t care, she would just talk to be people and be like, "Hey, can I help you? Hey, can I do this with you?" And they’re like, "Okay." And she just has... I don’t even know what she did that year. She has the most incredible stories, and I know a hundredth of what she’s done.

Jonathan Wow. So, she really looked at the program as an opportunity for a yearlong of travel, and she just immersed herself in the local culture completely.

Katherine Oh, yeah. Like, Carol would come to some of our events, and she would get up four a.m. and go to bed at ten p.m., so she was up all day. So, we have WhatsApp groups, and we’d wake up at whatever time, and Carol’s like, "Well, I’ve been out. I went here, here, and here. I recommend these restaurants and that museum." And that’s the other thing about Remote Year. You have all these friends that do these things, and so whatever you want, you’re just like, "Somebody tell me food," and then you get 20 suggestions. And now you have to figure it out yourself.

Jonathan That’s an opportunity for decision fatigue again.

Katherine Yeah, but it takes the research weight off, which was great.

Jonathan Yeah. Personal recommendations. That goes a long way.

Katherine Yeah.

Jonathan So, talking about someone that is totally green to working and traveling and that type of thing, what would be a great first destination for them?

Katherine So, Chiang Mai is one of those places that everyone talks about with digital nomads, and I wanted to go but I didn’t want to go right away, but it ended up happening because there was a digital nomad conference, the third one, in Chiang Mai, like the weekend after my Remote Year ended, and we were in Vietnam. So, a couple guys in my group were like, "Oh, let’s go do this." It’s like, all right, sure. I went to the conference and I was like, I’m just going to stay this month in Chiang Mai and check it out and see what the fuss is all about, because I’ve really only done the digital nomad thing by myself and with Remote Year. I haven’t participated in other communities. And Chiang Mai, I’d been before as a tourist. Going as a digital nomad, I consciously decided to stay in the super digital nomad-centric area, which is Nimman. And there’s a couple workspaces and a bunch of cafes with WiFi, and everybody you see there is either a backpacker, a digital nomad, or an Asian tourist from Korea or Japan doing these...professional or not, I don’t know, but crazy photo shoots. Like, every cafe and restaurant. It’s like they create them to be sets, and then people just come through all day, and they’re either working on a laptop, or they’re just doing photo shoots. And you’re like, am I here? Is this okay? It’s fantastic. But I think the reason people like Chiang Mai is because it’s somewhere that there’s definitely cultural stuff you can do. Like, Thai food is great. There are some other things. You can go up to the temples, go for some hikes. You can see some elephants. But it’s a really affordable place to go, and if you went, you could just work on your project. So, if you want to do a startup or something, or you’re just freelancing and you have to be on weird hours, it’s set up for that to be easy and affordable. So, I guess that’s somewhere you could go, and you’d meet a ton of people. It wasn’t my scene, but I think it was kind of like, if you came from Silicon Valley or you wanted to be part of that, but couldn’t quite do that, Chiang Mai is very much... It’s a little bit of a bro culture. They’re very nice. It’s a little bit of a bro culture and very dev-focused or drop shipping focused. So, if you’re interested in those things, then definitely a great place to start.

Jonathan So, what personality type did you typically see embracing this on the Remote Year and just as you’ve traveled around? Is it a very outgoing type person? Is it more of an introvert? Is there a mix?

Katherine Yeah, it’s definitely a mix, and I think Remote Year and any program is going to be even more of a mix, or maybe cater to a different group, because they are facilitating so much. So, a lot of people in the group hadn’t traveled as often or weren’t working remotely or whatever, and they saw this as a starting off point for doing that more. Or it was like, I want to do this for a year, and I’m not sure how to do it with my job, and I’m not sure how to do it logistically. So, this is a way that I can have some of that experience without the full responsibility of figuring it out. So, I definitely saw a huge range of people in our program. I don’t know what future program profiles will look like. I don’t know. I mean, in some ways, you’d think, yeah, people are really outgoing, and you can definitely socialize and do a lot of things. But in other ways, I’m clearly not shy, in many respect, and I’ve been a teacher and I’m totally comfortable performing and presenting and whatever. But I’m very shy and uncomfortable going to a party if I don’t know people or showing up somewhere, and I’m much more inclined to read a book or go to a museum and not talk to somebody or whatever. So, I would say I do the digital nomad thing when I’m by myself very independently, which is part of the reason it can be lonely, and I have to force myself to be friendly or be uncomfortable and go network or go socialize. But I don’t think it’s one or the other.

Jonathan So, the Remote Year is a year long. Are there shorter options out there? Are there month, two month-style programs that you’ve heard of?

Katherine Yeah. I think Remote Year is even doing something now where they’re doing, like, four-month programs. Because our itinerary was, like, four in South America, four months in Europe, and four in Southeast Asia. So, I think they’re now offering those chunks. But I do know there are many other programs. I think we list at least ten in the book, but I personally haven’t done them, so I can’t really speak to the experience, but I’m sure they’re great and there are a lot of options, and there’s options for ones where you join a group and travel, either month-to-month or several months. But there’s also a lot of things where it’s like a co-working space or a co-living space, and you’re not necessarily traveling with the group, but it’s like, I want to go to Bali and live in this co-living space, which means that I’ll be around people who are similar and who are living there and have similar goals and circumstances, not just backpackers and travelers, but digital nomads who want to be here for the month living together and socializing.

Jonathan So, looking forward, what are your plans going forward? Are you going to keep traveling? Is there a time when you feel it’s going to be done and you’re going to move onto something else?

Katherine My current plans involve flying from Bali to Zurich on March 31st, and I’ve booked an Airbnb in Paris for the month of May. So, that’s the only thing I know. So, like I said, when I started doing this, I just decided to keep going as long as I could afford to financially, and I’m still pretty much there. I am getting tired, obviously, because I’m a human. But I would like to see if there’s a way that I can set it up so that it’s not as exhausting, and maybe I try to find somewhere that I could do maybe two months at a time. But the thing is that, with my career and my income and everything right now, I can’t afford to go get myself an apartment somewhere and travel and do both, so it’s a choice. And given that choice, I’m still picking travel over living somewhere. But I’m sure that I do want to live somewhere one day, and currently, my storage unit’s outside New York and I love New York and that’s probably where I would go back. And so, it’s kind of like, at whatever point that there’s a job or a reason for me to move back to New York and I can afford to do so, that’s when I will live somewhere. Or something else will come along.

Jonathan Yep. Excellent. So, when people want to connect with you online, where should they find you?

Katherine Oh my gosh. I’m all over the place.

Jonathan Just use the Google.

Katherine It depends on what you want. Obviously, I have LinkedIn, which is there as a resume, I guess. I wrote on Medium several times a month. I try to make that... It’s hopefully less "Dear Diary", more information and interesting thought pieces, usually about travel, but sometimes about other things. So, Medium is a place that I use a lot. I post on Instagram pretty regularly, which all of these things are just my name, Katherine Conaway. I have a website that I...it’s nice, but I don’t know that works for any real purpose except to be there. Yeah, and you can send an email: hello@katherineconaway.com.

Jonathan Excellent. And we’ll put all these links in the show notes, too. So, thank you so much for joining us and sharing with us. We’ll make sure to have links to the book, which I highly recommend. Even if you don’t have an interest to go out and travel tomorrow, I found it a very interesting read. There was a ton of information in there. I’ll give you one little tidbit. They even cover how taxes can play into traveling yearlong, and depending on where your income falls, it may offset the cost of traveling significantly. So, that’s definitely something to check out.

Katherine That’s part of the reason I’m still traveling. [Laughs]

Jonathan [Laughs] So, there’s proof in the pudding right there. So, it’s definitely a benefit. But there was a huge number of things that I wouldn’t even have known to even search for, and it was a really well-written resource. So, I highly recommend it. We’ll put a link in the show notes, and thank you so much for your time.

So, that interview was a ton of fun, and one of the things I’ve really enjoyed with the Remote Works podcast is just meeting a wide variety of people, literally across the globe. And again, it was interesting listening to her entrance into being a digital nomad and how it was a very unintentional journey. She didn’t set out to travel the world for three plus years. It really just kind of happened, as she found enough work to keep sustaining her travel. And so, it was really interesting to hear how that played out.

Ari Yeah, definitely. I’d say everything she’s done at this has been on the road. Writing the book was on the road. The whole crowd she got, she learned from all these different people. Lots of very different kinds of people on the road with her.

Jonathan So, that was an interesting interview and I hope that you, our listeners, really enjoyed it. We certainly did. And the next section of the show is called "What’s the Buzz?", where we feature tips and books and other content that would be of interest. Ari, do you want to kick us off?

Ari Sure. So, there’s a relatively newer website out there called SpareDesk.co. That’s all one word, no hyphens. They actually have apps for, I believe, the iPhone and Android both, and it’s all about different co-working spaces, signing into there, and making available spare desks in their location. So, if you’re a digital nomad and you’re traveling around, you come into a city, you can just open up the app? It uses the location on your phone or on your computer. It says, okay, you’re in this city. Here’s the co-working spaces that we have listed, that may have or that actually shows which ones have available desks. Now, the list is still quite small. It’s a newer product still. But hopefully, our large audience can help grow this list by signing up, or getting their co-working spaces to sign up and increasing the number of co-working spaces available in different cities all around the globe? Great resources for our digital nomad especially, or just anybody who’s just looking to do a little bit of traveling at any time and needs to work where they are.

Jonathan Excellent. That’s really cool. So, mine this week is ISOtunes PRO, which is basically an in-ear Bluetooth headphone that I’ve been using the past couple of days, and they’re really lightweight, they wrap around the ear, and I wear glasses, and so sometimes, wearing headphones can be uncomfortable, and these have been super comfortable wearing with glasses and otherwise. And the thing that’s interesting, too, I’m looking forward to, is they have the ability to completely block out sound. They’re not noise canceling, but you can basically outfit them with more or less an earplug and wear them while you’re on a construction site or mowing the lawn, which will be my plan this summer, when the grass starts growing again and the snow goes away. And I think they also have a battery life of about ten hours, which is enough that you can use them all day long, and they have adjustable foam tips for the in-ear piece, so you can...they have a large, medium, and small, and then just kind of your standard in-ear setup. So, definitely recommend it. We’ll put links in the show notes.

Thank you for listening to the Remote Works podcast. This podcast is only half of the conversation. The other half is from you, our listeners. We appreciate your questions and feedback. Leave us a voicemail at remote.works/voicemail and we may incorporate it into a future episode.

Ari Subscribe to this podcast on iTunes, Google Play, Stitcher, or others. Please take a moment to leave us a review when you subscribe. Be sure to include your real name and mention your website or social media link, and we may incorporate the review in a future episode. The show notes, with links to resources, along with a full text transcript of this episode, is available at remote.works/9 for Episode 9.

Jonathan If you’d like to sponsor an episode or recommend a guest or topic for the show, visit us at remote.works. Finally, until next time, go be awesome! Thank you for listening. This is the Remote Works podcast. This podcast is a production of Cultivate Now, all rights reserved.

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