Last October, I gave up my expensive San Francisco apartment, gave away the few big things I did own, and flew to Amsterdam (through Iceland) with all my worldly possessions in two suitcases and a backpack. Since then, I’ve been to 12 countries and many more cities working from my 13” MacBook Pro. Being a digital nomad has always been my dream, but I was not nearly prepared for the reality of it. Learn what travel bloggers will not tell you about what it’s really like to be a digital nomad.

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Introduction (00:00)

Many of you know me as Natasha the Robot. I do iOS development, I run the This Week in Swift newsletter, I run the Swift job board, and I organize the try! Swift conference: we had one in Tokyo earlier this year, and we are doing one in New York in September. Today I am going to talk about my other alter identity, maybe my human identity, that passes the Turing test.

This is a picture from when I quit my job at Capital One. I was working in the San Francisco office and it was the best job I ever had, with amazing people. I :heart: my life in San Francisco at that point. But I have always wanted to be a digital nomad, and serendipitously, another company that does remote work offered me a job and I thought, “I have to do this. This is my chance to do it.”

At this point, I went to the UK. My friend there, Kate Houston, has a cute pink car, and she drove me around and showed me the Cadbury chocolate factory. After that I went to the NSSpain conference in Spain, because my other friend convinced me to go, and I went to the Grace Hopper conference, and another conference after that. Within a period of two months, when most of the time I was traveling, I had to wrap up my life in San Francisco.

I needed a home address, so I had to “move” to Seattle and live with a friend - technically, for tax reasons, but I didn’t spend time there, because I was traveling everywhere. I think you can also have an address abroad, but I do not - I travel all the time. I had a very stable, nice life, and I decided, “I am going to give it all up.”

This is the view from my apartment in San Francisco: really nice sunsets. This quote comes to mind. For me, the experience of travel is not only what I am seeing, but what I choose to leave behind, even for a short time, and the perspective I gain from doing that. Believe it or not, I do not know if I am addicted to doing this, but I love messing up my life and completely changing everything. Even learning to code was a complete career change; being a digital nomad is, to me, the same level of challenge.

My apartment was small. I always had the mindset of a digital nomad, I never accumulated things because even when I had a stable life in San Francisco for five years, I wanted to be able to leave tomorrow if I wanted to. This is all my possessions: two suitcases.

Since last October, I have traveled to 13 countries; apparently, I went around the world twice, and I am on my way to do the third trip around the world now. Currently I have spent 105 days on planes. This presentation was written in all these places: an Airbnb that I was staying in, coffee shops, on my ferry ride, in a pizza shop, in a van to the airport, in a hotel room, and on a plane- not necessarily in that order. That’s pretty much my life, working wherever I can, and always on the go, moving everywhere.

When you think of the term “digital nomad,” maybe you think it’s like a postcard, this dream where you are on a pretty beach. It’s the dream that you have of the life. When I look at travel bloggers, they seem to say, “look where I am now, it is pretty” and you think, “I’m in my annoying house, it is ugly and it is raining today” - I hate those people!

My first stop was Amsterdam, but on my way there, I stopped in Iceland - which looks like that dream, highly recommended. I had this hectic schedule before I moved where I was running around, I was trying to figure out how to break my lease and I had to throw stuff out (Craigslist!). The next step was Amsterdam, and what happened was something described in The Art of Travel: this book is not about how to travel, it’s analyzing art and how travel is portrayed, and it’s very philosophical.

“A momentous but until then overlooked fact was making itself apparent: I had inadvertently brought myself with me to the island”: this guy gets the postcard, the dream that we see (the beach postcard). It’s a beach vacation, he’s excited. But when you get there, you realize that you are there also. In real life experiences are usually different than what you see on that postcard. You cannot escape from yourself.

In normal life - where you have your routines you go to work, you have your workout classes, you have your favorite restaurants - it’s easy to not pay attention to yourself. It’s easy to get back into your routine and ignore what you’re thinking. But when you’re somewhere else, and all those normal things that you use for comfort are gone, then it is all yourself - which might not be pretty.

Amsterdam is one of my favorite cities. I was preparing for this journey, and I did not think about it much besides I wanted to do it and an opportunity came up. There, things did not go as planned. I realized I changed my lifestyle, I changed my jobs; all my friends are in San Francisco. I was also running my blog. I was doing This Week in Swift. I had started planning try! Swift in Tokyo (I had only been to Japan for two weeks before I planned try! Swift), which was challenging, (e.g., I didn’t speak the language and I had to organize a conference!). It turned out well, but at that point, that was a scary thing.

By the end of my stay in Amsterdam, which was about a month, I realized, “I cannot do this all, this is too much change. I have to give something up.” So I decided to give up my job.

This is a good quote, if you are into the zen meditation: “What is happening to you is nothing less than death and rebirth. What is dying is the entire way in which you understood ‘who you are’ and ‘how it all is.’ What is being reborn is the child of the Spirit for whom all things are new.”

I came from a stable, normal job in San Francisco with my favorite restaurants and my friends to “my life is completely different; everything is new.” It’s like a process of rebirth. But I’ve done this before, and I think we have all gone through stages where you have radical changes (e.g., when I moved away from home and I went to college and lived on campus; and after college, I moved to D.C. to work. Things didn’t work out, and I had to deal with that. Then San Francisco, one of the most radical: I came to visit for a weekend, and I quit my job, moved here, worked hard, ended up learning to code and switching careers). A completely different experience than what I came from.

I :heart: taking risks and resetting my life every once in a while. At that point, I was building my side business. I did not have to pay San Francisco rent, my side business made enough money to enable my lifestyle. The last challenge was learning to code.

When I was learning to code, I was shown this diagram, and it has always stayed with me (see video). There is this comfort zone (i.e., routine, you are good at your job): I hate being at that state. I need to be challenged, and this is where your stretch zone is. Even when I had the job, I had a side project that kept me challenged if my job was easy for me.

But if you stretch yourself too much, you will be in the panic zone. There’s this thin line between stretching yourself and panic. When you are in the panic zone, it is paralyzing. There is so much fear, you cannot do anything. You do not want to be in the panic zone, but the way I did my digital nomad thing, I put myself straight into the panic zone. There are many things that I did not know, and that I was surprised by, that I had to deal with.

I will talk about some of that: loneliness, sensory overload, language and cultural barriers, and productivity. Hopefully you will see similar ways of dealing with them to what I did. If you do want to do this type of thing, you have to know yourself really well because the things that apply to me, might be very different for you.

Loneliness (16:20)

I am an independent person. I have traveled on my own before. I spend weekends by myself. I go to restaurants by myself. But when I went to Amsterdam, I was shocked: I have nobody in the world. It was the worst loneliness feeling. I was surprised that that happened.

When I was living in San Francisco, I thought I was alone because I didn’t go out that much. But I went to work every day, and I loved my coworkers, and I hung out with them all day long. By the time I came home, I needed alone time, and I was fine being alone. But I didn’t realize how much social interaction I actually had every day. Then, suddenly, I had no more friends. I did talk to a few people in Amsterdam, but it was small talk, it still has this loneliness feeling. And that helps put you in the panic zone.

This is how I dealt with it: Skype! I didn’t use Skype when living in one place… I talked to my family over the phone. It felt like I was not alone anymore. Even though they are on the screen, it feels almost the same as spending time with them. It made me feel so much better. Whenever I do feel lonely, I will reach out to some of my good friends and ask them to Skype and catch up. It’s always an amazing experience.

We also have this great iOS community of people who live all around the world. I started being more aggressive about reaching out to people wherever I was going. When I came to Amsterdam, I probably waited one or two weeks before reaching out to people; by the time I was going to New Zealand - which was my next destination - I was already proactive:

• I asked someone on Twitter, who I knew from Australia, and they told me about a conference that was happening when I would be there. Immediately, when I landed in New Zealand, I was already part of the community. They were really nice and they drove me to the conference. It was around Christmas time: I am not a big holiday person, but one of them, Carl, invited me to his family’s Christmas, which was overwhelming that people do that.

• Matt organized an iOS meetup where we had Japanese pancakes, and afterward I made them go and take silly Japanese photos.

• In Warsaw, someone gave me a private tour of the city.

Reaching out to the community has been invaluable.

I also go to many conferences. Even though I might spend a month in one place, I might see the same person at a conference the next month. In the long term, it builds relationships (e.g., Boris, I have been to seven countries with him; Kate, we have been to five countries together). It’s really good to know the locals.

Shawn invited me for tacos at his house, and he made me a little bow, if you like arts and crafts, it’s really cool. I was organizing my own conference in Japan, and people came from all over the world that I could hang out with. I have adapted from, “I am going to go there,” to, “I know that part of my self care as a nomad is going to be meeting people,” and making sure that I do that.

At the Berlin Wall, there is this concept that you cannot be happy alone. My friends made me watch the movie The Lobster (really creepy: it’s set in this dystopian society where people have to be coupled or they get turned into animals). I think there’s a level of happiness that can be only experienced in a group, and an example of that is WWC. We are all excited about what is coming out and we have a higher level of consciousness because it is an energy in the room where everyone is projecting. And that level, as you have all experienced, is amazing and surreal.

In terms of everyday happiness, I get overwhelmed with the beauty of places like Amsterdam or Budapest. There are all these places where sometimes I walk around and I am overwhelmed, want to cry, because it’s so beautiful. When you’re with another person, you’re not guaranteed happiness; especially if you are traveling with a more negative person. It depends on the mindset. If you’re both in the right mindset, and you’re both happy and mystified by the experience, happiness gets even bigger, it multiplies. But if the other person’s not happy, it is a risk.

I find it hard to travel with other people now. And that’s because of this: “It seemed an advantage to be traveling alone. Our responses to the world are crucially molded by the company we keep, for we temper our curiosity to fit in with expectations of others.”

And that’s the problem. When I travel with other people, I have to make compromises. That’s the reality, you look at the postcard and it is perfect, but in reality if you travel with other people, it could be perfect (and sometimes it is), but I have also had experiences where I would rather be alone.

There is a balance. Traveling alone is amazing, but you do need people. I love the iOS community because it’s easy to go somewhere, go to a meet up, meet some people, talk to them, and they will bring me places, but I’m not tethered to them. I can go on and move somewhere else and meet other people, and then I will see them again. I’m not stuck with anyone who doesn’t like what I do.

Sensory Overload (29:32)

Here’s another quote from Vagabonding: “Transition into travel can be compared to childhood. Everything you see is new and emotionally affecting. Basic tasks like eating and sleeping take on a heightened significance, and entertainment can be found in the simplest curiosities and novelties.”

When I talk to people about being a digital nomad, they usually say: So you go on an adventure every day? But that to me would be too much. Instead, I go on many mini-adventures:

• Being in a foreign place and going grocery shopping is an adventure. Going to a workout class is an adventure. Eating out in a restaurant, definitely an adventure, because everything is different. Simple things, that people take for granted when living in one place, become really intensified when you’re traveling. You don’t even have to go skydiving or whatever. Just living in a new place is really intense.

• I like to eat. Food is most of my adventures. If you’ve seen the movie Jiro Dreams of Sushi, the sushi is definitely an experience. In Amsterdam, they have stroopwafels. In Zurich, there is this Japanese-style bakery.

• Once a week maybe I will do a bigger adventure, but most of my life is working, going out to eat, going out to exercise.

All of this is amazing but, at the same time, it is a complete sensory overload. It is mentally exhausting. You have to figure out: What is the grocery store? Where do I go? Where do I eat? How do I pay in this country? What if they don’t speak my language?.

Here are the things I do for myself to make sure that I get break time. The main thing is to have Airbnbs. I need a safe space where I can hide. Airbnbs are nice and have good WiFi. I usually work from there if I need a creative environment.

The other thing I do is run away and isolate myself (e.g., for this month and a half, I went to northern Washington, a small town called Port Townsend, and I didn’t talk to anyone for a month. I just went, ate healthy, exercised, and enjoyed the view. Sometimes it’s good enough to get away for a weekend - before my conference in Tokyo, and for my birthday I went to the onsen, which is an outdoors hot tub thing).

Finally, Gear headphones - I cannot recommend these noise cancelling headphones enough. They’re really expensive but amazing.

It comes to a balance: in some parts of my travel, I need the stimulus, meeting people, lights and excitement; other times I need to run away, have quiet, no stimulus, refresh and repeat the cycle.

Language and Cultural Barriers (39:36)

In most countries, there is no Amazon; I can’t get things delivered to my Airbnb. In Japan, I was only five minutes early to my yoga class, and they wouldn’t let me in. Grocery shopping, it is a stupid thing that would never happen when you know your environment… but, in Amsterdam, I did not know what the grocery shop was until I talked to locals! Also, they do not bag your groceries, and they did not accept American credit cards.

It is a intense experience; all these normal things are in the panic zone. The key is asking locals, and this goes back to that community (e.g., Sam from New Zealand sent me a long email outlining tips for a retreat I wanted to go to. Himi from Japan helped me research where to get my nails done. Minui in South Korea, he took us out to lunch and showed us around. In Amsterdam, I had a friend show me how to do public transportation). Reaching out to locals is key.

You have to cry and laugh about it, that is my coping mechanism. If you can’t do that, do not be a nomad.

Productivity (43:39)

Many people ask me, How do you get work done on the road?

In the office, the requirement is you have to show up for eight hours a day, but most of the time, you’re not working straight for eight hours a day (you might go to meetings, or go to the bathroom and grab some coffee, or answer your phone). When I had a remote job, that messed with my head and I thought: “Am I working enough? What is eight hours when you are not in the office?”.

That was one of the reasons I had to quit, because I could not figure out how to get myself out of that mindset even though they were not pressuring me. I was pressuring myself: Am I doing enough? Is this eight hours? Do I have to count my hours? This is weird. In creative work, I work best when I do not have set hours.

I work a lot, and I work on the weekends; but some days I will wake up and say, “I’m not going to be productive” (usually a result of working too much the last few days). I’ll go on an adventure that day, come back, and I’ll be refreshed and I will work again. In an office, you have to show up anyway, and then you’re depressed because you cannot contribute and other people are contributing, but you need a break.

The other trick is planning the projects I work on (such as planning try! Swift) required other people. I make sure that things I work with have accountability to other people. That way I cannot drop the ball, because people rely on me.

Travel is also an amazing motivation: “If I finish all my work today, I get to do something fun.” My work is efficient, taking care of the constraints versus before, in an office, “I am here from nine to five either way.” Being more efficient, you do not have to work as much, and you can do a mix of things.

Finally, I make sure to fly on Saturdays during the day. When I get there, if I have time, I try to unpack. Maybe Sunday I will go grocery shopping. Basically things you would normally do on the weekend, and maybe exercise, walk around the town, see what is around there. On Monday, I have food, I am unpacked, I am settled in a place, I am ready to work. Setting those habits is important.

Exercise, I mentioned that a few times. It’s very important; you do not want to get sick in a foreign country. Being healthy helps productivity.

Motivation is what keeps you started. Habit (e.g., exercise, waking up early, working) is what keeps you going and keeps you grounded. Routines can be taken on on the road and help make your life efficient. This is my favorite productivity hat.

I am very sun conscious, I need sunlight, or I get tired quickly. In November in Amsterdam, the Sun started to leave at four or five, and by six it felt like midnight to my body and I couldn’t work. I went to New Zealand. Apparently, there is a whole other part of the world where it is summer hours, and the Sun shines all day long. I’m doing a similar thing this year again, because I know that I will be productive if there is sunlight.

Summary (49:50)

Today I’ve talked about a few transformation functions or protocols. How to deal with different situations - to go from panic zone to stretching. There’s a nice zone where you’re learning and doing a lot. For each of you, those inputs and outputs could be different, but we all have those panic zone modes, and we need to have tools for dealing with them to be our most productive.

“You must live before you can die, but you must die before you can live.” That’s what being a digital nomad is, basically death and rebirth over and over and over again. Every time I go on a plane, I have to say goodbye to the people I met, I have to say goodbye to countries I love, to my routines that I have built over the month. I relearn my limits. Things that I thought were impossible I can now do. It has changed my assumptions about the world. I go to a new place and I have to do it all over again.

Q & A (50:27)

Q: I think you touched on this a bit, but with all the sensory overload, you were talking about all the beautiful places you see, all the time you spend traveling and going out, how do you keep your passion for software development going and not focus solely on the travel and the experiences that come along? Natasha: Most of the day I am working from nine to five, and going to conferences to make sure I learn new stuff. Before, I could learn it from coworkers, but I also went to meetups. I do hang out with people in the community, I get to learn from them. I am usually building something. Most of my days are boring. I eat, I sleep, I exercise, and I work. I guess in that regard, it has not changed. It is one of the things I am passionate about.

Q: So, are you done? What is your plan this year? Natasha: No, I’m not done (laughs); it is very addicting. I love it. This year I’m in New York for two months, until September. Then, I’m going to Italy for about two months. Then Singapore, Australia, probably New Zealand, back to Japan… and then other things happen.

Q: Do you have a round the world ticket? Natasha: Many times conferences cover my travel, or I have points on my credit cards. I’m covering my next two flights with credit card points. I don’t like to do a world ticket, because I do not know where I will go and I like the flexibility.