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The Realities and Challenges of Being a Digital Nomad

You jet around the world, a road and sky warrior armed with a laptop in search of a power socket and decent WiFi. No ties, no responsibilities; work when you need it and when you’re bored, you move on. Sounds perfect, doesn’t it?

The increased ability to work from almost anywhere for a wide variety of roles has seen the growth of a transient population of so-called ‘digital nomads’. I tend to stay put for longer periods of time than most, but have lived in four cities, am skilled in working on the road, and frequently associate with the most dedicated members of this tribe.

Many articles on the subject of ‘digital nomadery’ focus on how it compares to other styles of work, or on the glamour of such a lifestyle. Being pragmatic on many issues (you could say ‘British’) I thought it was high time to put together an article on some of the more challenging realities of the lifestyle and start discussion on how best to cope with them.

Let’s grab a budget airline flight to anywhere and get started.

Home alone

‘Mi casa’ is not always ‘Su casa’

As you travel the world, grabbing free WiFi in cafes to catch up on emails and plot the next groundbreaking blog post or cat photo sharing app, remember that the establishments you set up office in for the day are also businesses.

Staff deserve decent wages, bills need to paid, insurance covered, and suppliers paid for all that fair trade coffee and gluten free cake. Respect their rights to be a viable business and contribute accordingly. One coffee every four hours is not enough, bringing your own food is not acceptable. Weigh up what you are saving by not paying for a day in a co-working space and contribute accordingly. Depending on the location and how expensive the area is, I suggest a minimum of one item per hour. If the cafe is busy, and you’ve been there a while, then consider making space for others. It’s a popular misconception that a group of people sitting in a cafe for long periods of time are good for business. A regular stream of customers is far better, five customers per hour are generally better than one.

I understand if you can’t afford to rent a desk, or don’t have the need, but there are free places to work in wonderful locations such as libraries, shopping centers, and other community spaces. If you’re not able to contribute to the income of a business, then there are other options.

Isolation and loneliness

The nomadic lifestyle has it’s attractions. The ability to take advantage of high wages and low living costs, to pick and choose the climate you enjoy, to encounter interesting people and places, and unprecedented freedom.

However, you are a minority, and much of human nature and society is built around staying still.

It’s easy to be distracted by new experiences as a nomadic individual, but the truth is you can also spend a lot of time alone. It’s easy to meet new people, but can take a long time for others to accept you as a ‘friend’ instead of an ‘associate’. You may frequently find yourself excluded from events and gatherings reserved for closer friends, and people may find your gregarious ways confronting or intimidating.

This can be worse if you ever return to any of your ‘homes’. Those who remained behind have led their own lives without you, and no matter how much you stay in touch, you have missed out on shared events and experiences. You probably left for a reason, and are happy to have left certain attitudes behind, but it can instill a sense of sadness when you realize how much the world moves on without you.

Some cities have regular and easy to find events for new arrivals, so you will always find something to occupy your time. Other cities are less accessible to outsiders, and it can take a while to find activities that welcome you.

Co-working spaces, Facebook, Meetups and Slack channels can all be good sources to find social interaction.

Preparing for the future

Putting up walls

As the two-thousand-and-teens lumber on, I think it’s safe to say that the dreams some of us had about tearing down national borders are rapidly dying. Even the pinnacle of visa-free travel, the EU, is looking on increasingly shaky ground. If you are a resident of a Western (‘democratic’) nation, you’re likely to find getting visas (and this includes for tourism) easy for a lot of countries. If you want to travel off the beaten track, or you are a citizen of a less fortunate nation (diplomatically speaking), then visas will take you longer and be more complex to acquire. Even when you do get your hands on one, it’s worth checking what you are allowed to do whilst in a country. It’s unlikely you will be checked, but if you want to be cautious, it’s worth bearing in mind.

Nomad vs. the nation

Living in the moment it can be easy to forget about the future. Despite the opportunities that the modern world presents to us, countries have not changed that much, or change slowly. Governments like and expect their populations to follow certain paths that involve paying into systems and infrastructure. Systems like social security and healthcare are designed to cope with the potential that you might need them at an indeterminate time. The nomadic lifestyle doesn’t necessarily match with this, as we rarely stay long enough to pay into them, or if we do, access them.

As I near 40 and have so far called a handful of places ‘home’, I start to wonder about what will happen when I stop working, or am too old to want to anymore. If you have traveled extensively and frequently, where do you call home and who will look after you when you need it?

There are ways to prepare for the unexpected, like setting up investment account(s), or investing in private healthcare. These can become hard to maintain, and may not always be recognized in certain countries, but for now they are the best option. I would love to see an enterprising organization try to create institutions for the nomad in the future, but for now, here are a couple of more flexible global players.

Typically countries will start considering you a ‘resident’ and not a ‘tourist’ after a certain period of time. This varies for countries and nationalities, but bear in mind that some global and traveler plans may no longer be valid after certain periods of time.

Pensions and insurance

Some nations will support you when you are unable to work in the short term and/or long term. Unsurprisingly, they expect you to invest in these schemes, and short term residents may not be able to. You can cover these periods yourself with savings or investments, but I was interested to see if there was anything like an international social security or insurance fund.

Health care

Global healthcare to cover you at ‘home’ and overseas is a well established product, but naturally it’s expensive and inconsistent.

  • Bupa global, AXA PPP International and Aviva International – All the big players offer similar packages, but details are sketchy without entering into a pre-sales conversation.
  • Supplement your own – Depending on your home country and it’s healthcare system, there may be top up fees for global coverage.
  • Company offered – If you live and work remotely for one continuous employer, they may offer you healthcare (possibly through one of the suppliers listed above) as part of an employment package.
  • Medical tourism – A nomad is in a perfect position to take advantage of the growing trend of ‘medical tourism’, i.e. have treatment in cheaper countries than your own. The disclaimer above applies, just because you go elsewhere for treatment doesn’t mean that your current country of residence doesn’t expect you to have local cover.

If you’re interested in reading more on the topic, I recommend this blog post from Anna Wickham.

An important short-term consideration is that of medication. Medical and pharmaceutical regulations vary from country to country and forms of medication you rely on will vary in availability, dosage, and legality.

Job security and payment

There’s an obvious flipside to freedom, and that is insecurity. If you are a long established freelancer/contractor, you likely have a reasonable supply of reliable and consistent clients who keep the money coming in. But there can still be lean times (for example, December and January, or taking a holiday) where keeping on top of costs can be harder.

There are two broad solutions to helping this problem: one is confidence, and one is forward planning.

It can take a long time to gain confidence in yourself and your work to say no to bad clients and know that more will come, and that during lean times, having the confidence to know that it doesn’t mean the end.

Preparing for these lean times is a good skill to acquire. My main advice is to ensure you always have a buffer of money in savings to see you through at least three months before you start freelancing, and try to maintain it when you do have work flowing in. Set aside a portion of money every month to contribute to this fund, as you never know when you might need it. Knowing how to price your skills is an entire article in itself, but relates back to my point about confidence.

Security and privacy

I am far less security conscious than I should be with regards to my personal security and privacy, but I have seen other nomads who are so unconscious of security and privacy, that a breach is a matter of time.

There’s a fine line between security and paranoia, but that line has redefined itself on multiple occasions over the past couple of years and will continue to do so. My tips below are far from comprehensive, but I consider these actions you should take right now (I literally mean stop reading this and do them).

Device passwords

In most cases of laptop/phone/tablet theft, thieves will wipe it and your data is ‘safe’. This isn’t guaranteed, and there may be times when you are a direct target for data theft. Your device is potentially a gateway to all your other information, so it’s protection is tantamount. An increasing amount of devices now have fingerprint readers, but these remain unproven with regards to security. In summary, the password to your devices should be the most secure your memory can cope with, and don’t write it down. If you need advice on what constitutes a secure password, I recommend this article from the Carnegie Mellon school of computing .

A password manager

I feel like I shouldn’t need to mention this topic as so many others have discussed it, but secure passwords are incredibly important and a password manager will help you create and manage them. It’s such an easy tool to use, there’s no excuse not to. I lie slightly, as of course you need to remember your device password, and then the password for the manager (which should also be very secure), but two to remember is a lot better than dozens. For guidance in choosing a password manager, I recommend this PCMag article.

Leaking data

As a nomad or freelancer you will frequently connect to public (and possibly insecure) WiFi networks, receive files from a variety of sources and work with people with questionable security habits, thus exposing you. You can protect yourself from these threats by being aware of their potential existence and exercising caution. If you want to go a step further, then I recommend this post on how to stay safe on public wifi.

Keep calm and keep moving

This article was not meant to dissuade you from the many positives of a nomadic lifestyle, rather provide cautionary advice to make the it better for you and those around you. Flexibility and new experiences can be easy distractions from dealing with the minor irritations that real life throws your way. Enjoy yourself, do awesome work, but take care.

I would love to hear of problems you’ve encountered and how you solved them.

All illustrations by venimo

About the Author Chris Ward

Chris is a tech writer and blogger.