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This is what it’s really like to be a digital nomad


What is a digital nomad, exactly? Typically, it’s someone whose job can be done online and therefore, does not need to go into an office to work, meaning they can work from anywhere in the world (internet connection pending). It’s hardly surprising that it’s a very attractive job prospect for travel addicts, but when the job sounds as dreamy as this, we had to wonder, what’s it’s really like to be a digital nomad?

We sat down with Andrew Webb, a digital nomad originally from America, and asked him all the questions you’ve always wanted to know about a remote work lifestyle. From the good to the bad, and everything you need to know before taking the leap – this is what it’s really like to be a digital nomad.

What is your job?

I work as a full-time software engineer for a company based in San Francisco. We employ about 10 remote engineers (and ~20 in-office) from various places around the world: New York, Texas, Utah, Canada, Bulgaria, Lithuania, Australia – we don’t let location or time zone prevent us from hiring the best talent. Then, three times each year, everybody coordinates two-week visits to the HQ to have some social time together.

How did you decide to live the digital nomad life?

About five years ago, I was working remote from Boston for a different San Francisco based company. I grew up near Boston, and honestly don’t like it too much – I wanted something different. One day, while shoveling my car out of chest-height snow, I was thinking “why do I live here?” Then it hit me “Wait, really, why do I live here? I can work from anywhere with an internet connection.”

Years before, I had read books about the digital nomad idea (it was brand new at the time), and I started to realize that I was in the exact situation I dreamed about when I was younger. I told my landlord I wouldn’t be renewing my lease, and started making concrete plans to leave Boston. I was mad at myself for having not realized the potential of the situation sooner.


Image source:Andrew Webb

How long have you been a digital nomad for?

When I initially left Boston, I traveled for about two years, with various visits back home and to San Francisco for work, of course. I aimed to live in a new city each month, and two years in, I decided to go to Austin, Texas and it instantly stole my heart. I decided to sign a lease and stay in Austin. After two years of uprooting my life on the first of each month, the idea of a year-long commitment scared me, but I went through with it, and ended up staying a second year too. After two years in Austin, I ran into some issues moving apartments that left me without a place to live, so I ended up deciding to work from Japan for a couple months before coming back to figure things out. While I was there, I realized that I missed the excitement of moving around so much, so I decided to get back into the lifestyle. Excluding the stint in Austin, I’ve been a digital nomad for about 2.5yrs, but I’ve been working full-time remote for 6yrs now.


How did you prepare for a life on the road?

Well, there are some logistical choices you have to make before you’re ready to go anywhere:

Are you going to be somebody who keeps a storage unit of things back home, or are you ready to get rid of everything and keep only a few boxes of personal possessions in a family-member’s basement? For me, I kept a medium-sized storage unit with quite a lot of stuff. I regret that now. When I eventually opened it and started going through it, two things happened. First, I said “Why did I think I should save this?” way more times than expected. Second, it acted as a time capsule, reminding me of when I was miserable and living in Boston – did I really want to bring that negative emotional attachment with me to my new life in Austin? It reminded me of how different my life and my identity were from just two years prior. Now in Austin, I have a tiny storage unit (I have no family there to keep things with, plus it’s dirt cheap), with mostly clothes and my motorcycle that I didn’t have time to sell before I left.

Another decision you’ll have to make is how fast you want to travel. Keep in mind this isn’t a vacation – I’d argue that if you’re working at the same time, you should be spending at least two weeks in each place. I know people that travel faster than that, but for me, I aim for one or two months in each place. Many digital nomads will spend more than six months in places, doing visa runs to extend trips. It’s up to you how intimately you want to get to know a place before moving on.

One of the most important decisions to make is what type of accommodation you’re going to live in. Personally, I tend to switch between entire Airbnb apartments and co-living spaces when I’m feeling lonely, but there are a lot of choices: you can save a ton of money living in hostels, but it’s a little weird to stay long-term in one, and do you really want to put on sandals every day to shower? Entire Airbnbs are great, but can be a bit lonely. Co-living is an attractive option for meeting people in similar situations with work, but they’re usually more expensive. Private room Airbnb’s can be awkward if you often have meetings at night and worry about disturbing roommates. Hotels, I wouldn’t ever consider due to poor internet and lack of real-life amenities like a kitchen or washer/dryer.

The more tangible choices include: choosing luggage (I live out of a carry-on and a small backpack that holds only my laptop and camera), choosing what goes in that luggage, and selecting the first places you’re going to go. Those are the fun choices you can make once you’ve already decided how you’re going to make the transition.


Image source:Contiki

What does a normal day-in-the-life look like for you?

This is possibly the most important thing to consider before becoming a digital nomad. Without a job, you can’t have this life. My previous job actually had a silly rule against working from anywhere besides where you were supposed to be living (for me, Boston), so I worked American time zones no matter where I was, and never sat near a window during video chats where they could see that it wasn’t daylight outside. Blank white walls were my best friend, and I even traveled with a day-light white lightbulb that I had to employ sometimes to give a false impression it was daytime.

Now, at my new job, they don’t care at all where I am, and encourage me to work whatever time zone feels comfortable for me when I’m abroad. Some days I work my local hours and handle meetings via written communication earlier in the day, other days I spend the daytime exploring my new city and align my work hours with my team at evening or overnight. It’s all about being overly-communicative and at least somewhat flexible. I’m super fortunate to work for a company that is as serious about remote working as I am.

For those that don’t have a remote job right now, but in theory their work could be done completely remote, you can start by having a discussion about simply working from home on a frequent basis. Even if you can work from home once a week, this allows you to take three-day weekends to places. From there, you can talk to your company about the major benefits of allowing remote work, such as:

How far ahead do you plan where you’ll be?

This is embarrassing. I plan incredibly far ahead; I’m booked up all the way through the end of 2019 right now. It’s ridiculous that I do this, I don’t even like planning, but I really like online shopping, and since I can’t use Amazon to feed my addiction when living out of a suitcase, I satisfy my craving by booking accommodation. Unfortunately, travelling to places for a month or two at a time, I can only indulge this vice a handful of times a year before I’ve completely filled up a calendar year.

There are some benefits to living the digital nomad life. For example, month-long holiday rentals are very hard to find on short notice, especially during tourist seasons. If a place is even rented out for a single day during the month and the host would actually gladly cancel, it won’t show up during my search. Of course, I could split up the month among a few different rentals, but most will have huge monthly discounts for stays of over 28 days.

On the flip side, I can’t change my plans last minute because I book so far in advance. Yesterday, my friends asked me about going to London for New Year’s Eve, but I’m spending time there in the fall and if I go back that soon, I’m dangerously close to the maximum time I can visit per-year without becoming tax-liable.


Image source:Contiki

How many new places have you travelled to since you started being a digital nomad?

Counting only places I have stayed for at least three weeks, about 35 cities, across 20 countries. Of course, there are a lot of side trips I’ve taken – I try to take a weekend in each place I stay to explore a nearby place. With some places, like Madrid (where I am now), I was sure I’d enjoy it, so I just booked an apartment for the month. But some places I’m unsure about, so I try to visit when I’m staying somewhere nearby. For example, last weekend I went to Marrakech, and while it’s not a city I am dying to spend a month in, I found out that I do definitely want to go back to Morocco for a longer visit to explore the country’s other cities.

What are the best things about being a digital nomad?

The feeling of complete freedom. Nothing is keeping me anywhere – If Seoul is getting a bit too hot in summer, I can head to Melbourne. If I’m really missing my friends in London, I’ll just book a flight and go see them. There’s no limitations with having to request time off at work, because I’ll be working no matter where I am, so I can go anywhere at the drop of a hat. There are also some smaller freedoms that you don’t realize until you’re remote: waking up whenever you want, going to the gym at less crowded times, having no commute, not putting pants on for three days straight.

The other best thing is getting to know cities like a local, not only through the eyes of a tourist. When you’re just visiting as a tourist, each morning you’re digging through a suitcase trying to figure out which clothes are still clean and rushing around to all the major sightseeing spots. But when you’re spending a month or two in each place, you start to establish patterns that make you feel more at home – you’re not constantly stressed about trying to fit everything into your short visit. You’ll do laundry, you’ll cook at home, and most importantly, you’ll start to get recognized by your local bartenders,


Image source:Contiki

What are the worst things about being a digital nomad?

There’s a few actually. It’s definitely not the fantasy lifestyle everyone imagines! One of the worst things is the decision paralysis that comes with complete freedom: like, should I spend July in Prague, Sydney or Hawaii? Wait, what about friends back home who have summers off of work – they’ll meet me somewhere in Europe, but they want to visit 10 cities in 10 days. Maybe I should visit home, my friends have new babies that I still haven’t met. Perhaps I should focus on my Spanish and go to Peru. When everywhere is an option, it’s really hard to choose a single place to be without incurring huge FOMO. (Spoiler alert: I chose Hawaii for this summer)

Another struggle with the lifestyle is the constant guilt of not being around those you love. My mother would love to have me around all the time – and I don’t think she ever imagined I’d have the ability to literally be by her side 24/7 and I’d choose not to be. Imagine this with somebody you’re dating – there’s no real reason you’re away from them for months at a time besides you just choosing to be. It’s a really hard decision to make, and it’s easy to feel guilty for making it.

I guess another issue with being a digital nomad is that everyone you meet is either confused by your lifestyle, envious of it, or thinks you’re going through some personal crisis and avoiding responsibilities for a while. Nobody thinks it’s normal, and that gets very tiring. So many times, I just wish I could answer people’s small talk questions about my job with “I’m an accountant” and end the conversation. I always dread answering those questions when first meeting people.

Making new friends is also incredibly hard. No locals want to become friends with someone who’s only around for the next month. It’s much easier to meet other travelers though, even though it gives you less of a “local” experience.

The last ‘worst’ thing is that it gets very tiring living life in another language. When you’re changing locations every month, it doesn’t make sense to invest time in studying a language only to never use it again after four weeks. I always learn enough to talk to a cashier or order a meal, but that’s it. For anything more complicated I always have to Google translate before and mentally rehearse before saying it out loud.

What misconceptions do people have about it?

There’s a huge clickbait culture online about digital nomads. It propagates this misconception that we’ve “hacked life” or that we’re somehow living a counterculture lifestyle. We’re not, we’re just the newest form of hipsters.

You can find a million blog posts with titles like “I quit my job to travel the world and don’t regret it for one second” or “I sold my belongings, bought a van, and now I’m never sad.” All these posts propagate the fake positivity that comes with Instagram culture. Everybody is afraid that being honest and saying that something wasn’t “the absolutely best cup of coffee ever! #almondmilk” will make you lose followers. That is only exaggerated by the loneliness you experience as a digital nomad – you can’t risk losing followers and weakening your only connection back to the real world. Social media becomes much more important to digital nomads and we end up in these types of articles glamorizing our lives.

In actuality, my real life is nothing like all these articles pretend that this lifestyle is. Most of the nomads I know live basically the same no matter where they are: Spend the majority of the day working, eat rushed meals between meetings, and spend maybe a couple hours a day seeing the city we’re in, waiting for weekends to really explore. It’s how most people live, remote or not. We just have more exotic social media posts and it gives a false impression that every part of our lives is different, but just remember that you’re only seeing the highlights.

A woman embracing the digital nomad lifestyle walks on train tracks in a desert.

Image source:Contiki

What traits/skills/personality do you think people need to be an efficient digital nomad?

The most important trait you’ll need is discipline. You need to be able to separate work from travel, and that can be really hard sometimes. You’ll want to go out and meet new people, or wander around the streets to explore, but you also have to attend a work meeting that’s at an inconvenient time. Of course, this isn’t like your normal “work from home” day that a lot of people might take advantage of a little and work a little less. That’s a special thing for non-remote workers. If you worked every single day from home, it wouldn’t be special anymore, and people would notice if you weren’t outputting the same amount of work.

You need to be able to stay cool under pressure. This is required when traveling in general, but once you’re traveling 24/7, things go wrong a lot more often. Trains are late. You miss flights. You’ll be unable to find food late night (I often starved in Switzerland). You’ll get sick and have nobody else to help. These things happen, and there’s nothing you can do, so you’ll need to be able to handle them yourself.

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