Digital Nomads

SOLO 48 | Digital Nomad



One of the benefits of being solo is optionality. You can do more with your life than the standard Monday through Friday 9-to-5 (or these days 8-to-6). This week’s episode explores an intriguing idea: give up your residence and head out on the road to live and work. The rise of the digital nomad lifestyle has been fueled by the rise of remote work, Airbnb, and other technological advances. Peter McGraw is joined by a digital nomad, Jesse Thomas, and a return guest, Lisa Slavid, to give you an initial glimpse into this exciting yet challenging lifestyle.

Listen to Episode #48 here


Digital Nomads

One of the benefits of being solo is optionality. You can do more with your life than the standard. Monday through Friday 9:00 to 5:00 or these days, 8:00 to 6:00. This episode explores an intriguing idea. Give up your residence and head out on the road to live and work. The rise of the digital nomad lifestyle has been fueled by the rise of remote work, Airbnb and other technological advances. I’m joined by an enthusiastic digital nomad, Jesse Thomas, and a return guest, Lisa Slavid, who is new to the digital nomad game. They give you an initial glimpse into this exciting yet challenging lifestyle. We talk tips, tricks and pitfalls, but the thing that I like most about the episode is the use of a theme to help you make decisions about where to go and what to do. Chasing food, weather or other available singles. I hope you enjoy the episode. Let’s get started.

Our guest is Jesse Thomas. He is the CEO and Founder of JESS3, a creative interactive agency specializing in data visualization. Described as, “One of the web’s hottest designers,” by Mashable, his firm has worked with organizations such as Nike, NASA, Facebook, Google, Samsung and the World Bank. He joins us from Puerto Rico by way of Antigua by way of Alaska to discuss his life as a digital nomad. Welcome, Jesse.

Thanks so much for having me.

We are joined by a previous guest and now guest cohost, Lisa Slavid. Lisa’s an expert in strategic planning, positive psychology, strength building, motivation and innovation. She has over 25 years of experience designing, learning workshops, programs and keynote speeches. She works with organizations from corporations, universities and nonprofits. She’s an organizational consultant, an executive coach, a Semester At Sea Trustee and the Creator of the published Peadoodles cartoon series, which you must check out on Instagram. Lisa appeared in Episode 17, which feels like a long time ago, titled Lisa’s Second Mountain, where we discuss her plans to be a digital nomad. She was living in Santa Barbara at the time. She now joins us from Hot Springs, Arkansas. Welcome back, Lisa.

Thanks for having me back.

It’s great to have the two of you on the show. This has been the most difficult one to set up. This is what happens when you try to get to digital nomads into a remote space at the same time. Jesse, you are joining us from Puerto Rico. I’m not interested in how you got to Puerto Rico, but I’m interested in how you became a digital nomad and how’s it going for you?

It’s going great. When I think about where I was years ago, I was intrigued by web design as a business, as an ability to be a freelancer or to have my own little thing so that I could do this exact thing. The cool thing about having your own consultancy is that you can charge the prices you want to charge and you can spend the money the way you want to spend it. Most importantly, you can use your time and your schedule it how you see fit. It’s a great luxury that we don’t think about these 9:00 to 5:00 jobs. You might be an executive or a manager, whatever, if you show up one time late, you could get fired. That’s so crazy. Trying to avoid being fired and still have fun and then adapting that into having as much fun as possible.

You’ve already said three things that are fascinating to me. The first one is you started off in this web design world, is that right? It has blossomed into being a full-on creative agency that you run. In this way, you sound different than the typical digital nomad. What is the typical digital nomad and how are you different?

I started out as a one-man show that created a portfolio for myself. Back in the day, your Flickr name, your AIM instant messenger name, all these names had to be coordinated. The URL happened. It was my portfolio for my own personal work. I had jobs. I worked at AOL, I worked at Ogilvy PR. I was at another PR firm in the DC area. All the while on the side, my projects and stuff, I would put on this website. From there, I created an agency and we do more things and then of course the web design industry has changed. People don’t need websites anymore.

We have adapted to that and content would be the way to think of this new bucket. That includes infographics and all forms of visual content, as well as animations and short films, which is a super-hot thing that more than half of the work we’re doing right now is around short films that are less than a minute long thing. The traditional digital nomad, when I think of the years ago version, the classic digital nomad is like a web developer, perhaps a web designer that is working off of their laptop. That idea with the laptop that you could work remotely with this desktop replacement and then the internet made that possible.

All those things came together and then the mobile web being a part of that as well. As a young person, I think of it as somebody in their twenties perhaps or mentally in their twenties who are living month to month, on a lease that might be month to month. When we think of the term nomad, we might think it’s 1 to 3 months. Sometimes these people are staying in these places for a year. I don’t know. What do you call that? A digital nomad is more of a frame of mind and a commitment to living like that over a long period of time.

What you’ll find is you can sustain that lifestyle of, “I’ll stay here for a year.” You get in a relationship. You’re going to stay for a couple of years versus the month to month stuff is quite tricky to sustain. Financially, not everybody can do that. It’s draining because there is so much travel and then packing up your stuff. You’ve also got to pick the right places. Every once in a while, you’re going to pick the wrong place. You’re going to be stuck in that wrong place for a month or whatever. Finding the right spot and picking the right amount of time to be there is part of it. One thing that a lot about with my traveling is being in the right place at the right time. Whether it’s in Africa for the great migration or you want to be in the New England area when it’s in the summer, you want to be in the United Kingdom in the summer. You don’t want to be there in the winter. Some of the basic stuff like that. I’m always thinking about seasonal travel and the effects of that on where you’re going. You don’t want to be in Chicago in the middle of winter without your snow jacket.

Jesse, can you share with us what else makes a place attractive to you? If appropriate, can you share where you’ve gotten stuck?

Where should Lisa avoid? That’s what she’s asking.

Instagram changed the digital nomad travel world. One of the things that I do a lot of is I’m saving into a folder the name of a place or a city or a country. I’m keeping track of the stuff that I want to recreate on Instagram and then on a list, in a note as well, in particular. I’m also saving things in Google Maps. If I see some great steak or some cool cow or whatever it is on some photo, I’m like, “Let me find that thing.” Let me find it on Google Maps. I try to save it in those different places. Most importantly, I keep a list of all the places that I’m planning to travel to.

Most of the things that are going to end up on that list are food-related. I travel for food. I had a place in Nashville where it was an Airbnb. One of the things about is sometimes people will incorrectly list the property. You’ve got the entire home designation, which is probably the most desirable, and you’ve got shared and we’ve got the private. This guy had his music studio in the apartment. This is a three-bedroom apartment. One of the bedrooms had his music studio. We rent the place we show up and he’s like, “I’m going to come by tomorrow to work on some music. I’ll let myself in. I’ll be in the studio. Don’t worry. I might be in the kitchen.” I’m like, “What?”

Now I know why this was such a screaming deal.

In this case, I had been duped and it was more of a case. That Airbnb is loosey-goosey sometimes on some of those classifications. They want to be on the side of the baluster and not being telling them what to do. Sometimes you get those weird non-entire homes. Sometimes you’ll get a house listing. It’ll say entire home, entire house or whatever and then the owner lives in the basement underneath.

These are fun stories. I don’t want to go too deep in them because you’re basically going to convince people to not be a digital nomad before you convince them.

I got great stories too. Those are some funny random ones. This is the thing. When you’re saving money, you’re cutting corners. You’re used to a hotel lifestyle where everything is a square deal. You get a refund. In Airbnb, you’re going to get the refunds if things aren’t right. There’s a lot of gray area with Airbnb. You can take advantage of that as well though.

I already hear you and Lisa is already trying to hone in on one of these considerations. I want to talk about Lisa’s decision making about where you’re going to live or where you’re living. It sounds like there’s this one issue of a requirement for this job is some flexibility. That is that you can work it on different time zones and that you need connectivity, but you don’t need to be meeting face to face with clients in the same room and so on. This is where the initial nomads came from. Obviously, the rise of Airbnb and the internet makes it easier. Work aside, you have the flexibility to go where you want to go. I had come across this idea of digital nomadship lately. I was in Berlin visiting one of my friends.

He offhandedly told me about some guy who works at Tech Crunch who’s a digital nomad. I was like, “What exactly is the digital nomad?” He’s like, “Someone who’s without an official home, moves around, they need a laptop and a phone,” and so on. I went down the rabbit hole studying this stuff. Frankly, at times, I’m fantasizing about it. One of the themes was Berlin in the summer, Bali in the winter. You’re chasing warmth. One consideration is you were in Alaska in the summer, obviously not in the winter. The other one might be a personal desire. You’re chasing food. We had chatted briefly before this. You chase fruit. Is that right, Jesse? You’re a fruit chaser. When we were warming up here, I asked what you had for breakfast. What did you say?

I had gotten some great mangoes from a farmer. I had them in the fridge. They’re perfect. Cold, large, and amazing.

You chase fruit as part of your choice among places, yes?

Yes. I grew up in the DC area. My family is from New Zealand and I did spend a bit of time there. In the DC area, it’s like any major city, you go to Whole Foods and you can find a dragon fruit or a starfruit or whatever if you’re looking. They have a very small section of exotic fruits or whatever. The problem with starting with the pineapple or the banana, bananas are picked green. A bunch of them are green. Pineapples are still firm and greenish. Nine days can go by from the time that they’re picked to the time that you purchase it at Whole Foods. You don’t know if it’s 90 days or 60 days or 30 days, you have no idea of time. It’s not like meat. They don’t feel the need to put any date on things you got to look at. One of the problems is at your local supermarket, even Whole Foods, the nicest supermarket you can possibly get your hands on, the exotic fruit is still always going to be questionable. Most people that aren’t into food or in the food business or whatever aren’t ever going to dabble in that stuff.

It should be clear to the readers that you are indeed chasing fruit in a variety of ways in your life. Lisa, you’re in Hot Springs, Arkansas, what are you chasing there?

I was chasing basically getting to have a summer with the family with my awesome nephews, and they still think I’m pretty cool. I wanted to get some time with them and time with family. Time in a new location to explore and see similar to what Jesse was saying like, “Could I live here sometime in the future, at least part-time and have a family here?” I’ve lived for years in Santa Barbara and it’s gorgeous, but I don’t want to be chained to that lullaby. I want to get out and run around a little bit more, but I want to draw fruit hunters as a cartoonist and coqui frogs. What strikes me is this as you’re doing this, it sounds like Jesse, you’re articulating so well having a passion for something, a pursuit. You mentioned photography and food and street art, but then fruit. You have passions that make a place come alive for you.

It’s a big world. You have to make some choices about where you’re going to be, even if it’s for a month. You want to try to optimize those elements. Let’s step back. Let’s imagine the person who’s reading who’s contemplating this. The reason I wanted to do a digital nomad episode is because single people have flexibility. They don’t have kids in school and a partner who has a job that they have to do a 9:00 to 5:00 necessarily. They can pick up and move. It’s an ideal lifestyle and I get the sense listening to you, Jesse, this is going to be temporary. It would be hard to spend twenty years as a digital nomad. At some point, it’s going to wear on you, but it can be exciting in the meantime.

You’re going to find the X on the map. You’re going to find the treasure, the rainbow. You’re going to fall in love with somebody or you’re going to break your leg or you’re going to run out of money. What you’re getting to, which is an important part of traveling and the perspective that I’ve gotten that over all these years of traveling is budgeting. One of the key things you got to think about is how much money are you spending in your current position. Let’s call that $2,000, the average person let’s say. You’re thinking in your month you have a car, you don’t have a car. In my case, I didn’t have a car. I was using Uber to get around. I have an understanding of what I’m spending in a month. Budgeting is so important. The tip that I want to give everybody is the Airbnb 30-day savings.

[bctt tweet=”Be flexible because things are going to go sideways. You have to be able to adapt.” via=”no”]

These are Airbnb, monthly rental. It’s a new-ish feature.

That’s what I’m talking about. When you’re searching for an Airbnb for 30 days or more, and there is a specific monthly search category, it takes you the same place. You’re able to access discounts that the lister has chosen to put in there. They’re not always going to be there. They’re constantly changing how you view those discounts. You’ve got to click all the way through click to the price. I’m going to show you the discount. I’m able to find discounts for 90% and everything in between. Let’s call it an average of 50%. You can look at the Maldives right now and you could put in that November to December and you can find places that are 50% or more off. Back to that number, the $2,000 number that the average person is probably working with.

One of the big things about budgeting that you got to think about is room and board, transportation, food, entertainment. Those first two are important. Transportation, when you’re renting a car around the world, I paid as little as $500 on the island of Molokai in Hawaii, cash deal, local car rental place. You can pay as much as $2,000 a month to rent a car in the United Kingdom or someplace. It’s going to be in between that to have a car. If you’re working with $2,000 or less, you’re going to have to figure something out on transportation. For example, go to a place like Paris, go to a place like the Maldives where you’re going to be on an Island. You don’t need a car. You can save half your budget because that’s about what it’s going to cut. You can share that expense, obviously, which is a whole other thing. If you’re focusing on what you’ve got to spend, it has to be in that order. Budgeting is so important.

You are saying to the person who is considering doing this, the first thing you got to think about is what’s your burn rate? Where do you want to go? What’s it going to cost? What’s your monthly nut, so to speak? It seems to me that there’s the other side of that, which is where’s your income coming from? What are you going to be living on? How much of this is going to be savings-based? How much of this is going to be the money that you’re going to be making? How steady is your income? How variant is it? How good is business and so on? It seems to me those two things go hand in hand. Part of the reason I would struggle as a digital nomad is because I’ve gotten used to fancy things. I would have been a great digital nomad at 27 as a grad student, but right now I’m like, “I guess I’ll do this,” in a sense. What’s your job? Can you continue to make good enough money not in your home city? It seems to me what you’re alluding to is some jobs are better than others in terms of making decent money and covering that.

I got nothing but bad news for you on that front. Web design and digital design, designing infographics and animations design, that’s a great business. I got lots of tips around that, but I see a lot of people struggling and I see a lot of poverty in my travels. I don’t know. I see people living cheaply, the people that travel in those hostels and stuff. There’s a lot in between the young hostile traveler and then the middle-aged single digital nomad. One thing you touched on that I wanted to bring back to is stuff. You’re saying you’re living luxuriously. You have all this stuff. You have all these physical things as well.

Putting stuff in storage, which is the first step, that is where the movie begins. There’s an expense to that. The cost of that in a year to have your storage locker, the difference in cost going to be $2,000 a year to be in the city. It can be half that price if you go out into the suburbs and go into the rural areas. That’s one of the tricks I learned is with those storage units, the more out in the rural part, the cheaper they’re going to be because it is square footage. You’re basically renting an apartment with no stuff in it. That is what the business is.

In fact, they will sometimes name the alleyways that you have, your storage lockers, as streets, and they are landlords. A couple of things to think about with that is you need to have your stuff in proper storage because you don’t want to be thinking about your stuff getting damaged. One of the key things about these cheaper storage places is they often are not managing the heat. Let’s say you’re in Alabama where it can get hot or you’re in Chicago and get cold and hot, your stuff can get damaged in the cheaper storage companies. What you want to do is make sure you’re sticking with a chain, a big company, and you want to make sure that the temperature is managing all your stuff. That’s another one of your expenses. The last thing you want is to be digital nomading and you’ve run out of money and you think, “I got to pay the storage bill.” You got to think about how you’re going to pay your storage bill as well.

That was going to be one of my questions is where do you put your stuff? It was like the George Carlin Illusion.

I had four storage units around the country. I had two in the Los Angeles area. I had two in the DC area basically. I had four at once. Over time you consolidate them.

I’ve downsized. The flip side of that question too is what stuff do you take with you?

When you’re traveling solo, one of my first tips for people that I love to bring up is on your laptop, I like to bring with me vintage game controllers that plug into the laptop. I’m playing arcade games, retro games and modern games on the laptop. Your laptop and your different media devices, that’s the first thing you want to get. With the iPad and the iPhone, you have the tablet and the phone. You have the ability to offline download movies. That’s step number one. My tip on that is YouTube has a premium feature that allows you to offline download content. There’s a feature of YouTube called Watch Later where you’re constantly like saving things to your watch later folder or whatever.

Think of it as a playlist. You can set that to be downloaded. All the stuff that you’ve saved can be put there. What they’re doing now is they’re adding things into these playlists that you’re offline downloading like suggested downloads. There’s a lot you can do with this offline downloading. The same goes for Spotify. You want to have the biggest storage you possibly can. That’s tip number one for being a digital nomad is making sure that all of your digital devices have as much storage as possible. You want to fill them all up with entertainment content, not necessarily like your backup of all your photos. You want to make sure you’ve got those movies, renting movies, buying movies and all that stuff. You want to get that library locked down because sometimes you’ll literally be without the internet. You’ve got these devices. That’s one key thing.

Jesse, you are forgetting how advanced you are in the world of digital nomadship. Let’s step back for a second. You need a phone, you need a laptop. It sounds like it would help to have an iPad or some tablet also.

Not necessarily the tablet.

You need those two things. Obviously, you need a passport.

You don’t need much else though. This is the key thing. This should interject on that. There are food things. There you’ve got your bathroom bag, you’ve got your food bag. In your food bag right now, I’ve got things like my manual espresso maker and a bag of sugar and a bag of salt and a pepper grinder. Sometimes in takeout bags, they’ll give you the knife and fork with a napkin or plastic spoons and stuff like that. I’ll have a little collection of that at any given time. High quality, ready ground coffee that I can put it in my espresso maker. That would be one key thing. I always have a sketchbook and pens with me. I bought a Game Boy. I’ve always got some retro game thing going on, books and clothes. The trick is you don’t want to over-pack. When you’re thinking of what to pack, rule number one needs to be don’t pack more than you need. I’m a big fan of under packing on the clothing for like the t-shirts or the tops because you can buy those at that cool bar you go to. You can buy that cool hoodie at the place or whatever.

What happened in this case, I started traveling in November 2020. I traveled to New Zealand where I’m from. All my bags were stolen at the beginning of my trip. I started over buying things on this trip. I’ve gone out of my way to buy things on the road and then replaced the specific things that I was missing. I’ve gone through this mental exercise. I went through it, to begin with like, “What did I need to bring on the trip?” When that was challenged, I had to buy those things remotely and then deal with not having them, including the laptop, by the way. I literally got the laptop. I’ve been doing my work on the phone.

How did you get your bag stolen? This sounds like a nightmare for a digital nomad.

It’s a nightmare, but it’s real life. The real quick story. Outside of my grandmother’s house, my cousin lives in his house out in this lovely little city called Rotorua. It’s a tourist town in New Zealand. I had put my stuff, my bags in the trunk of my parents’ car that I was using. The next morning, I was going to leave and I had planned to leave night the day before, but I ended up staying. My bags stayed in the car and I slept in the extra bed thing. When I woke up the next day, the bags were missing. What had happened is this thief couple who specialize in breaking into unlocked cars. I’d left the doors unlocked, but it was in the trunk. They had stolen this stuff. Months later, they catch them. They still had my suitcase. It still had my baggage tag and my name on it. I did get the suitcase. My cousin has a suitcase. Stuff like that happens. They got everything. I had some cash there, all the devices, but not the phone. I had one pair of shoes and that’s become a joke on this trip. I have traveled the world with one pair of Sperry Boat shoes. One pair of shoes is all you need. No socks.

It makes me think of something and I’m on a budget right now because I’m in a life transition. I do have some nice equipment and so I extra ensure it, which is not that expensive. It’d be a pro tip to anybody thinking about doing this is contact whoever provides your insurance and you can get certain items added on. I have some camera gear that is insured. If anything happens to it, even internationally, it’s like $50 a year and it’s great peace of mind.

What about insurance?

I asked a digital nomad master who has the thing, the mile method. Here’s the question that I posed to him, which I’ve always wondered. I never know if I’ve gotten this right about medical insurance. Here’s the question. There is some international coverage where you pick one country, but you still have worldwide coverage. Of course, it’s questionable how good that coverage is going to be. A lot of the international coverage asks you in advance to pre-select where you’re going. That’s one challenge for medical insurance. You might not know where you’re going and it’s tricky to commit to something. You’re like, “What if I go to Africa? What if I didn’t?”

The question I pose to the mile method is this. I said to him, “What insurance do you use?” He said, “Here’s the thing. I would rather out of pocket in the country and pay the full price than worry about being overcharged on the insurance that isn’t going to cover what I need anyway.” That’s basically his take on it and that’s my take on it. When you’re in Costa Rica, the hospital system, you’re hoping will be affordable. If you need to be on from Tanzania to South Africa or from the big city to the small city of the big city that you’re you would pay that out of pocket versus paying. Think about how much medical insurance is a year.

For you kids at home that have never had to pay your own insurance, think about what this number is going to be. It can be as little as $2,000 or $3,000 a year. It can be like more $4,000 or $5,000 a year. Over a decade of your twenties, you’re basically spending $50,000 on insurance. That’s a lot of money. If you’re in between the middle class and upper class, you understand how money works. You want all of it to spend on that on the thing you’re spending money on that day, you could argue that the reckless approach is pay out of pocket. In the back of your mind, you’re saying, “I would have paid $50,000 over this every decade.” That’s $50,000 you could spend out of pocket. That’s the challenge you have to take on is are you going to third world countries where they’re not going to even respect the insurance you’ve got and you’re going to be playing games and chasing waterfalls on the coverage that’s not going to cover you.

It looks like we’ve covered many of the basics here. Obviously, the budgeting, make sure you have a job that is mobile, that can finance this lifestyle, both the digital stuff, as well as the stuff that you need. It sounds like a little bit of what you’re considering is what are the basic things that you absolutely need to leave a little bit of creature comforts, whether it be entertainment-based or your coffee in these different places. Operating pretty lean sounds like the key to this.

Buy on the fly. That’s the key to that. The idea that when you’re there, you’ve got room in your suitcase to buy that shirt or you’ve got room in your stomach to buy that extra thing at the market because you didn’t preplan and buy everything at the supermarket when you got there. You thought, “Let me see how it goes.” A travel philosophy is less. You don’t need all that stuff because you’re going to have to carry that stuff. You’re going to have to carry somebody else’s bag too. You’re going to be stuck with it. You’ve got to drag it. Your wheels are going to break. Everything’s going to go wrong. You’re going to have to carry the bag. The handles are going to break on top. You got to hold it from the bottom. Everything’s going to go wrong. It’s going to rain.

Lisa and I both, I mentioned at the outset that she’s a trustee for Semester At Sea. Both she and I have participated in Semester At Sea. It has a little bit of both of these elements where you have this luxurious, comfortable space while you’re on this ship going around the world. You’re in India or Brazil or South Africa, Vietnam or any number of places. You’re mixing it up and you might be rather lean for 4 or 5 days out there in the world. One of the things that get preached on the ship, which sounds apt, is this notion of flexibility. Things are going to go sideways. You have to be able to adapt. It’s interesting to watch the students and the staff and the faculty on Semester At Sea at first struggle with that. By the end, they’re like grizzled veterans. They can move adeptly through a culture. After being on the ground for one hour, they can figure things out.

One thing that you reminded me of there is the fear when we travel. The idea that we’re scared that we’re not going to be able to get the things we want when we’re there so we have to bring them in advance. We’re scared that instead of going to the farmer’s market up the street in the third world country, as everybody else does, we’re like, “No, that could be dangerous.” One of the things you learn very quickly and what attracts women to travel is that that’s a myth. I grew up in the DC area. There are neighborhoods in DC that are super dangerous where you literally could be physically attacked or die at 10:00 in the morning thing. It’s not the same in some of these other places.

Depending on where you’re coming from, your idea of fear is going to drive a lot of your decisions. It’s a cool experience to disarm yourself and to allow yourself to be part of a community and to ask questions. One of the cool things about Airbnb is this is like staying with your uncle or something. They will call their relatives and say, “This single person’s here. Go on a date with them.” “This person here has a flat tire. Go help them.” “This person likes fresh fruit. Bring him some fruit,” whatever. They’re pulling their Rolodex out for you. That experience is typically reserved for the concierge experience at a Four Seasons or something. They’ll do that for you there, but they’ll charge you every step of the way.

You don’t always know if that’s the organic experience and you’re lucky if you find it. Airbnb, like couch surfing before it, the whole idea of that community is that you are going to ask for favors. When you’re in the third world traveling on Airbnb, that becomes very important. You might be in a place that’s got political unrest and this person is helping you stay alive or you’re in a place that has very strict rules. When you arrive with immigration, this person’s got to be on the phone with them. This is like an uncle. This is like a relative that can do so much or so little. Whether you’re being a digital nomad or not, embracing this idea of having a local connection that if you got into a problem, you might call them back. “Talk to these guys.” That happens where you put the Airbnb host to somebody who has given you some static about whatever. Without that, it wouldn’t have gone as well as it did back then.

I have a comment and then a follow-up question too. My comment is Jesse, I love how you said like be disarmed, immerse yourself in the culture and the place. That’s part of the beauty of it. We’re not going to another place to have the same fast food we could have at home. I would say though, one of the things I’ve been finding is a digital nomad as a woman as I drove across the country or came to a new place, I’m pretty friendly. I smile the people, but I don’t know the place. As a woman, there is an extra layer of travel, especially solo traveling, to be like, “Is it cool for me to hike alone here?” I try to feel that out. There’s some extra to that.

I had a follow-up question for you that connects to social. I love what you said about Airbnb that they’re like your uncle. I’m lucky enough that I’m an artist. I already painted the woman’s house who I’m subletting this from right now. It’s sweet to bring little gifts or offer something. My follow up question for you too, because you’ve done more of this than I have, is the social aspect. You’re in place for a month. How do you connect? What happens if your friends are halfway across the world and it’s nighttime? Who do you hang out with besides the Airbnb uncle connection?

Traveling as a woman, what you’re saying or what I understand about that, the complexity of that is that as a woman, and also it is depending on how physically strong you are as a guy as well, there’s a scale of how open and disarmed you could ever be. As a guy, you think, “I’m ready. Let’s fight.” Maybe women are never going to be that crazy and be willing to even be that open with it. They’ll always be very reserved about the security. That’s a tricky one. With Airbnb, let’s say that you’ve gone out of your way to find a female host or maybe it’s a person of color host or whatever it is you feel comfortable with.

Maybe it’s an LGBT host or whatever it is, or maybe this is the person that you know or that you’ve connected with on the road that can help you guide you on that safety journey. That’s basically all you can do. In your case, it’s the aunt. The cool aunt that is going to give you that insight, but you’ve also got to pick and choose places that you have that understanding of they’re going to work with how you were trying to travel.

There are two things. Obviously, Tinder and the online dating scene is a mobile thing. It’s an international thing. It’s the same thing with Uber. When you get into a city, it’s like, “Is Uber a thing here or does it have a different name?” Same thing with Tinder. Some cities have Tinder, other countries have different things but it works the same way. Online dating is still a thing. Regular dating is still a thing. You can still use the same tricks. You go out with your Airbnb hosts on a Friday night with a bunch of young single people and go that route or do you do what you’re normally doing with your online dating? The dating, it’s as hard to meet somebody at a new place as it is to meet somebody in another place.

My second thing is Facebook events are great. Before that, you had all these different services that pulled together events in single places. That’s what Facebook events are now. It’s a great single place to find all kinds of events. One of the things I have found great luck with is the VFW, the Veterans of Foreign War. You’re in a rural place, like I was in Alaska or in Hawaii, which I traveled to back the back. I found myself in these rural communities where nothing else was open and they would have like a sausage pancake breakfast on a Saturday and they’d have like a fish fry on a Tuesday and you rock up to these places.

It’s the coolest thing. There’s a bar there. It’s older people. They’re square. You’re in Hawaii, you’re in Alaska, whatever. They do these events on a regular basis. That right there is a classic trick, whether it’s the VFW or the Facebook events in particular to tap into a local community. Also, game nights are fun. I found myself randomly meeting cool people there because those are the kinds of people that are willing to meet people. We played Scrabble. There was a Scrabble night at a Hawaiian game thing that I found on Facebook and it was super fun. Random stuff like that. Normally pre-COVID, you have actual events to go to. Sporting events, music events, lifestyle events, food events, etc. That’s why people travel.

Back to Facebook events, how do you find those places? Facebook event is a good answer to that. When you’re in Google Maps, Google Maps will even show you the RSS feed of the locations of events. It’s hard to test this now because nobody’s doing events, but you can find events. Google and Facebook are doing a great job. Google does a similar thing to Facebook wherein Google, if you search for events in Honolulu, they have a very nice interface of people they’ve collected event listings from different places. Facebook, Google is the answer to that.

Those are great tips. It reminds me of a story about you, Pete, because you can flip it about being welcoming to whoever’s visiting your area and go the extra mile to help them out like this. This isn’t about, “How do we figure out how other people can help us out when we travel?” It’s how do we welcome people I. Pete, I’m remembering a story about you meeting a woman traveling who had like a long layover and it was in LA. She was from Asia. You’re like, “Let me give you a tour.” This is not ringing a bell for you?

No, and not because I don’t think it didn’t happen, but because I probably have done that a number of times in my life where I befriend someone who’s from out of town and say, “What are you interested in? Let me give you some tips.” Jess, your response about Facebook events and the dating apps. I’m a big fan of a Meetup, especially if I’m in a city, not in a rural community. If I’m in a city, I’ll go on Meetup and I’ll look for a writing group. They oftentimes are held either like on a weekend, maybe a morning or a weekday in the evening.

They’re usually at a coffee shop or a cafe or something like that. I love going to those because you walk in there and everybody introduces himself, talks about what they’re meeting so you get a flavor for who’s in the room. Everybody’s friendly, then you write for 1 or 2 hours. You sit in front of your computer and write, and then in the end, people usually stick around and have a conversation and it’s a great way to meet people. I like the fact that there’s this digital thread through all of this. There are machines that you need to do the job. There’s the Airbnb to get your places, there are the dating apps to get your dates, there’s the Facebook’s and Meetups and to get your places and then to get your transportation and so on. It’s such an exciting world.

There’s a highlight though, a tension between the three of us. There’s this idea of being open to new experiences. Saying yes in a world that you might not normally say yes to, being open to chatting with strangers, something you might not do in your own hometown and so on versus safety. Versus I don’t want to get myself into a thing where I’m getting ripped off, where I might get assaulted. Lisa, your question is an interesting one. Our joke when we were young was being a big dumb guy. I get to move through the world fairly comfortably at my height and the way I carry myself and so on. Still, is it daylight? Is it nighttime?

Daylight always has that easier element to it in terms of finding where people being out on the streets and so on. What is the method of transportation? I think of going to Mexico City and what’s the state of the art? What are the best practices so you don’t get kidnapped? You can move through that place in a way that’s safe or you can move through that place that’s unsafe. As you were saying, Jesse, doing a little bit of research to figure out where to go and when to go. My other tip is I like to find a cafe. When I’m traveling, obviously not as a digital nomad, but if I’m traveling, especially if I’m going to be in a place for 1 or 2 weeks, I often try to find a cafe to start my day. It’s interesting. You can become a regular pretty quickly. In three days, you’re a regular. They get to know your name. They know what you’re going to order, they become a resource and also a place of entertainment.

It’s everybody that you’re touching. It’s the Airbnb host. When you walk out the door, you say, “Is it Tuesday?” He might say, “The trains are closed on Tuesdays so make sure you go this way.” This is the Airbnb host. You’re taking that Uber and the Uber guy says, “There’s a protest starting down there. Make sure you’re not there at 5:00. They’re going to have the big alarm bells.” You’re at the cafe and then it’s the waiter. You’re saying, “Later I’m going to go by that protest at 5:00.” They say, “No, don’t go on 5:00. Go at 7:00.” Every step of the way you’re communicating, you’re keeping notes, mental notes and written notes, but that’s it that’s. One of the things about traveling is when you go back to living in your town or wherever it is, you end up coming back to, you take those tricks with you.

You’re more willing to talk to the person there as well because you have those same conversations that help them, if you’re lucky. One of my things though, aside from trying to be a regular at one spot, my strategy is to go to a different place every day of the week, breakfast, lunch, dinner, and in between. My goal is to rack up new places and to go out of my way to go to a new coffee place every single day. If I find a place that I love and there isn’t a better place on the list, it has more reviews, it looked better, I will go back. I do try to go out of my way to go to a new place because that’s how luck works with places.

It’s so hard to judge a book by its cover. You do get better and better at judging books by their cover. You can still do that with the Google Maps photos and stuff. They categorize the photos. They’ve got photos of the menu. They got photos of the food. They’ve got photos of the interior and exterior. You can also read the reviews and understand how people are writing. You can understand who the people are, how they’re writing and what they’re writing and the photos they’re taking and how they’re composing those photos. You can understand the place. You got to take the time to do that though.

I have a question for both of you. Let’s talk about fitness. Lisa, you are moving from Santa Barbara, which might be one of the easiest places in the world to stay fit to Hot Springs, Arkansas, which seems like not an easy place to stay fit. I’m curious about how you’re adapting. Jesse, since you’ve had more experience, what are some tips that you guys have?

That’s what I’ve been trying to navigate. For summertime, it is hot. Part of it is going out early in the morning and then I love hiking, but early in the morning, there’s not a lot of people hiking because people are doing their 8:00 to 5:00. That’s where I have felt a little bit enclosed, especially during COVID. I’m not sure exactly where to go, but it’s been getting up and getting out and doing something physical every day. I’ll put on some music and I’ll dance to doing chores or whatnot to move. What’s cool is that I have enough space here. I have a yoga mat spread out. I don’t have to roll it up. I can stretch every morning. That’s what I do.

I try that. I do somewhere things where I’m going out of my way to go on longer walks or walks in places and hikes and stuff that I’ve never done before. You’ve got that thrilling combination of not just fitness, but you’re doing something. The cool thing about traveling is you find yourself losing weight for two key reasons. One is you’re doing more physical exercise than normal. You’re out seeing things standing up and doing stuff. You’re using your body in unique ways. Your diet is different. Most people, when you’re doing a weekend trip, you’re ordering extra bacon, you’re getting the extra dessert with everything. A lot of American travelers fall into the bucket of what we’ll call the cruise traveler or the all-inclusive traveler.

I remember having a conversation with someone on a cruise ship once trying to talk them out of this lifestyle, trying to talk them into the Airbnb lifestyle. The woman was in a hot tub. She’s like, “I paid $35 or whatever it is for the premium all you can drink glass. I’ve had five drinks already.” They literally are thinking about maximizing their consumption. That’s a short travel thing. When you’re traveling for a long period of time or you’re doing this digital nomad stuff, the Eat, Pray, Love name and brand and story and book and lifestyle, that’s a real thing. People are doing the eco, travel, yoga, vegan thing, and there’s a trail for that. One of the cool things is combining your passion, which might be this eco, vegan, yoga lifestyle and going to the places you’ve always wanted to go and go to Bali or go to Hawaii and find all those places that the yoga teacher’s eating at and be one with that community. That’s the thing. That’s not my thing, but I like being around those types of people. I need to get into that though. That would be good.

I want to do a couple of quick faster hitting answers. Jesse, how do you manage your client’s expectations? You run an agency that produces high-quality output for big corporate clients. These are people working not a 9:00 to 5:00, but an 8:00 to 6:00. These are hard-charging individuals, and yet, if someone follows you on Instagram, they see your pictures of reindeers and they see your pictures and videos of protests in Portland and they see lots of mangoes and so on. How is it that you manage the fact that you’re doing high-quality work, but it looks like you’re goofing off all the time?

When you’re younger, it’s harder to pull that off. If you’re in your twenties and you’re doing luxurious things on your Instagram, that’s a cliché. Depending on where you’re coming from, depending on where your family’s coming from, with money, obviously, that’s going to influence how you travel and how you put yourself out there. It’s a two-sided challenge. On one hand, my clients are looking at my stuff. On the other side, my teammates are looking at my stuff. My competitors are looking at us, everybody’s looking at whatever. You’ve got to be authentic, but you don’t want to seem distracted. What I am doing and what I am I’m lucky that I’m able to do is prove to myself that I can have fun, but then also create a great work product at a price that the clients like to pay. Clients understand that I’m a unique individual so I can get away with that. I’m lucky that I’m in that position, that I have this creative agency that I can be fun with.

Hearing you talk about this, it seems like you play by a different set of rules. That is what would be a bug for most people is a feature for you. Jesse’s this creative individual. He’s a bit of a globe trotter. Let’s see if we can nail him down, but he’s going to deliver versus the person who might be a little less experienced, have less expertise, be still cutting their teeth where they might need to downplay a little bit of that there. Is that fair to say?

That is fair to say, but here’s the educational bit for people that are reading and what they can do with their lives. Whenever I talk to a young designer, a young person that isn’t a designer, or even anybody in this audience is the importance of a team. The reason that I’m able to live like this is because I have an incredible team of people that make the work look great. If you want to have a lifestyle, we’ll call this the manager lifestyle. The words that I chose are important. Manager and executive. Managers and executives have a different thing going on because they’re making more money, they have more control. Their next move is going to be a bigger thing or something.

The point that I’m trying to get across to this broader audience that doesn’t necessarily want to have a creative agency is how is a team going to happen under your management? You are never going to be a millionaire as an employee. Nobody’s ever going to pay you $1 million. Do you want to be a millionaire? You’re going to be lucky to make $100,000. You’re going to be super lucky to make $150,000 in your lifetime as a salary. If you can figure out how to be the manager of your own company, how to own your own company, how to be your own executive, start up your own thing or whatever, you’re going to have a team of people that are going to do work while you’re fishing. While you’re sleeping in, these younger people, whatever the work is, they’re going to be doing it while you’re over here.

That is something that you have to earn. You can imagine setting something like that up and then it fails while you’re on the road. I got all sorts of stories to tell you about that stuff as well. That’s what you’re dealing with. You take the time to set something up that you can manage remotely. You think to yourself, “This could be managed remotely.” You step away and you test that out. Depending on what team you’re managing, you’re always at risk of that thing falling apart. Are you managing a hot dog stand from Bali that’s in New York City? Are you managing a creative agency? These are different things, but the importance of the team and to have this lifestyle, you have to understand, you have to manage a team. You have to own a company that has employees to live like this. A single employee, you can only make so much. It can only do so much. It’s an important thing to figure out that team service that you want to offer that might attract you to do it.

I think you answered the next question, which was sent to me by Kim which is, what’s the best career for digital nomadship? It sounds to me like you’re saying you’re not a single operator, but rather you’re doing more project management-related stuff.

Consulting is something that is very specific and not everybody can do that. Only 15% of people can do consulting. That’s a tricky one. That is true. I don’t have good things to tell you about that.

Lisa, you chose well with your particular skillset.

I looked into that. Being an artist too and there are probably going to be phases. I would say to somebody who’s considering this if you’re considering it between career choices or between jobs, that anything you could do, get a taste of it if you can. Most people are working remotely right now. The luxury of Hot Springs, Arkansas is it’s beautiful. There are cool things to do outside. It’s also unbelievably inexpensive. I’m saving money by traveling right now.

As I was thinking this through, in my last book, I talk about how regular, everyday people should consider a sabbatical. In many ways, the sabbatical is an ideal time to consider digital nomadship. It’s going to force you out of your comfort zones. You might have saved the money to be able to live on so you don’t have to work too much. You can treat it as more of adventure first, work second. You can try out a new life and then you have something to come back to.

Most people might have mom and dad pay half the trip money. A lot of people are doing those things at the early start of their life where mom and dad are still paying for things.

My last thing is how do you avoid burnout? I want you to answer this for Lisa. Lisa is getting started on this. This is all new. She’s figuring this stuff out. How do you avoid that idea of like, “I don’t feel like I have a home. This is starting to wear me down,” and so on.

Always having a backup plan for where would you go if you get injured, where do you go if you’re depressed or you’re running out of energy. That place might be your home or your second home, or some family place. There’s that. Generally, security is what you’re looking for in that backup plan. For me, one of the things I think a lot about is like what would I do if I had one project and my budget was more like $1,000 a month or whatever. For $500 a month, you can be in the Maldives. You can stay in Paris for $500 a month. This $500 a month number, I think a lot about. I’m constantly on Airbnb, checking out what is the lowest price for a month rental that’s a Superhost classification and a place that I might want to be. I’m constantly gleeful when I find a listing where I’m like, “That’s incredible.” For $1,000, you can get this house or $500, you get this apartment for a month in a place. Financial security is another key thing you usually want to always think about like, “Where am I going to go if the money goes a bit low?”

That’s something to think about because your money does fluctuate when you’re living like this. You always want to think about where do I go for financial security or family time or visiting friends? Visiting friends and family is the key thing for this lifestyle. You’re connecting the dots. You’re thinking, “I’m going to go here for the family reunion. I’m going to go to this wedding. I’m going to visit my friend at his house here,” and you’re trying to connect. You’re keeping track of people you can stay with. You’re keeping track of people you want to visit. When you’re on the road, you find yourself keeping in touch with those people you think in the back of your mind, “I might want to visit that person.” For me, it was a friend that I needed to send packages to or whatever. Sometimes you need favors along the road and you want to make sure that you’re staying in touch with your support team, your friends and your people that are going to be able to help you if you’re in a disaster, your good friends.

Lisa, what’s your reaction to that?

I like the idea of the backup plan and checking in with yourself. If you hit a lull or a low spot, “This is where I go. These are my buddies that I stay with for a couple of weeks while I’m swinging through to that.” It also makes me think about like, “This is so complicated, but how cool would it be if it was easy to buy like a five-bedroom house someplace in the middle of the country that’s not very expensive.” You team up with other digital nomads, so people stay behind, they take care of the pets and you always have your room, but then you’re off for a couple of months and then you come through and they’re off. Some kind of a home base like that would be cool. That’s the thing about being a digital nomad is that it doesn’t need to be a location like outside of DC or Boston or Europe or LA. It could be in Montana. It could be in Arkansas. There are lots of cool places.

This is such a digital nomad thing for us to have done given that we’re in three different places and using laptops and the internet to be able to record this. As I said, this is a nice little fantasy for me. We’ll see a post COVID do I take some of this out for a spin, so to speak? I want to say, Lisa, thank you for coming back. As I had said in the previous episode, I’m so thrilled for you climbing your second mountain and it’s good to see you taking these initial steps and clearly thriving, albeit sweaty.

Jesse, it’s great to connect with you further as an expert in this. As someone who’s very clearly passionate about this lifestyle and realistic about its pros and cons, you’ve been a welcome voice in terms of people. Anybody reading this is not going to get a false sense that this is either great or terrible. It has opportunities, but it also has costs. I want to thank you so much for taking the time away from your Instagram pictures and videos, as well as from the management of your award-winning creative agency. With that, I’m going to say thanks to both of you.


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About Jesse Thomas

SOLO 48 | Digital Nomad

Jesse Thomas is the CEO and founder of JESS3, a creative interactive agency specializing in data visualization. Described as “one of the Web’s Hottest Designers” by Mashable, Thomas has been working toward owning his own agency since he was in his late teens. Obsessed with comic books, MTV and video games, Thomas has built a company that produces the wonderment and magic he remains inspired by for awesome clients like Nike, NASA, Facebook, Google, Samsung and The World Bank.

About Lisa Slavid

SOLO 48 | Digital NomadI help people and organizations reach their highest potential. I do this through the frameworks of positive psychology,appreciative inquiry, creativity and innovation. 


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