Can I Truly Work from Anywhere?

Are you, or would you like to be, a Digital Nomad?

If you’ve spent much time on Instagram, you’ve probably seen the promise of it: work from paradise, live inexpensively, perhaps even pay lower taxes. And when you feel like it, move on to somewhere new. Basically, do work fully on your terms.

Sounds pretty good, right?

We have people in our programs who describe themselves as Digital Nomads, and I’ve worked from over 30 countries myself, so for some time, it’s been something I’ve wanted to learn more about. A few months ago, I was given the opportunity to do exactly that when I was invited to speak at an event organized by Plumia, a think tank with a mission to advance the rights of global citizens and build infrastructure and coalitions for a borderless future. The event would feature a diverse and eclectic mix of academics, founders, and policymakers from around the world, many of whom had personally lived the digital nomad lifestyle for years.

And last week, the conference finally arrived. It was held at a place you might see a digital nomad – a lovely coastal resort in Morocco (Essaouira) – here I am living my own version of the Digital Nomad lifestyle!

In today’s newsletter, I want to share with you five key fundamental questions I’ve had about Digital Nomads, and the answers I’ve now found, because the event really changed my perception of what Digital Nomadism means to the people who live the lifestyle and the places they work from. I suspect you will find it useful, even if you’ve never dreamed of being a digital nomad or employing one, because digital nomads tell us fascinating things about what’s possible when it comes to integrating work with the rest of our lives.

Question 1: Why Do People Become Digital Nomads?

As with almost everything related to human behavior, the answer to this question is complicated and nuanced. Based on my conversations with digital nomads, I’d break it down into four broad categories – Lifestyle, Ideology, Optimization, and Necessity.

Lifestyle is often what comes to mind when we think of digital nomads. The theory here is that you get to integrate work into your life in a way that fulfills you. You want to travel, immerse yourself in culture, meet new people, and try new foods, and you don’t accept that you need to wait until retirement to do so. After all, if you can work from anywhere, why not turn work into a workcation?

Some digital nomads look at this as something more than just enjoyable and enriching, though. They see nomadism as supporting their ideology about the world. It points towards a future world beyond borders – where people have the freedom to live anywhere and work anywhere, and where there are no barriers to doing so. They long for a day when anyone can be a citizen of the world and when people live in communities based on shared values, rather than being restricted by the accident of their birth. They see their own nomadism as part of this broader movement.

The optimizers are typically individuals who view nomadism as a means of preserving more of their time and money. Perhaps they see low-tax locations and look to spend exactly the right amount of time in each location to minimize the tax they pay, either as individuals or for their businesses. They may still enjoy digital nomadism, but really, it’s a means to an end.

And finally, there are the people whose existing circumstances mean a form of nomadism is necessary, or even essential. This could include individuals facing persecution in their current location or those who are in physical danger. So, they have to move where they work from, sometimes multiple times.

Now, of course, people might share several of these motives, but having met and worked with people in all four categories, it’s become pretty clear to me that this is a highly diverse group of people who all have their own reasons for nomadism.

If any of these reasons apply to you, there is some good news. If you want to be a digital nomad, there are numerous locations that are eager to have you. Why? Well, for many of the same reasons that they appreciate tourists. Tourists spend money, and sometimes bring in additional foreign investment. In fact, many of the locations that strongly advocate for digital nomadism are places that lost significant tourism revenue during the COVID pandemic.

Question 2: What Challenges do Digital Nomads Face?

Digital nomadism might feel like pure freedom, but in reality, there’s an awful lot of planning you need to make it work, starting with getting to where you want to be. Different countries have different policies, and those policies may apply differently to people coming from different countries. In fact, your ability to move freely around the world is massively determined by where you were born. A Digital Nomad born in Europe or the US will have a very different experience than one born in Kenya, for example. Then, of course, you have to figure out where to live in your chosen location, where you will get your work done, and how you will make it all work financially.

Then there is the difficulty of getting the support you need. You might get sick, so you have to figure out how to get health insurance that will work as you travel. If you have school-age kids (and yes, some nomads do), there is the challenge of consistently getting a quality education for your child as you move around. You need to determine how and where to file taxes, and possibly establish a pension. You’ll also need the support of some form of community to combat the loneliness that digital nomads often report over time. That can be much harder if you are never in one place for long.

Finally, there is the challenge of getting and keeping work reliably. To remain consistently employable over time, you must ensure that your skills are up to date and that you’ve built and maintained a network of potential employers who are comfortable with the way you work.

This last challenge may become a more significant issue over time. As I discussed in Is Flexible Work Dying – as technology like AI continues to advance, many of the jobs likely to disappear early are the ones that can be defined most precisely. That often corresponds to gig work, and gig work is what many digital nomads rely on today.

Not only that, but we are starting to see that when it comes to firing people, workers who are remote from their employers are more vulnerable to being let go. This shouldn’t be surprising – after all, most managers, if they have to fire someone, will be more tempted to get rid of the person they have rarely or never met. It’s just human nature to favor people with whom you have a closer relationship.

Question 3: What digital skills and capabilities do digital nomads have or lack?

There is one capability that digital nomads possess in greater abundance than most other employees, due to their lifestyle. And the good news is that it’s practically the most important skill an employee or gig worker can have: adaptability. The digital nomads we’ve assessed possess this skill because they are constantly adapting as they move from location to location.

What other supporting durable skills do digital nomads typically acquire well due to their lifestyle? We’ve found that they score strongly in time management, organization, expectation setting, written communication, working independently, and resilience. These are all durable skills that not only serve them well today, but will also serve them well in the future.

But there are also areas where digital nomads can struggle. Perhaps the most important is collaboration, and specifically real-time collaboration. Organizations are valuing this more, as they realize that human collaboration in real time can produce different types of results and can also deepen relationships between colleagues. Other areas where digital nomads typically score lower include real-time communication, relationship management, conflict resolution, and workplace ambiguity.

Of course, everyone is different, but these patterns are not surprising. It’s essential to remember that durable skills are like muscles – work on them, and they will become stronger; fail to work on them, and they will weaken.

As technology continues to advance, the need for top-notch soft skills will only increase. So what should Digital Nomads do to hone theirs? We’d propose a modified strength builder approach. Yes, nomads are likely very adaptable already, but with some additional work in this area, they can improve their adaptability further, showcase it, and make it a differentiator for them.

Then, of course, they need to do some work on the other critical soft skills that organizations value now and will value more in the future. That should be achieved through a combination of experiential learning programs, like the ones we offer, and by seeking opportunities outside their gig work – for example, by volunteering in their local adopted community.

Question 4: What’s needed for sustainable digital nomadism?

I’ve already mentioned that digital nomads can be beneficial to a location by acting as a financial boost. That’s why places as diverse as Carribean Islands, Lisbon, Estsonia, Malaysia and Japan are creating incentives.

However, despite the Instagram view, Digital Nomadism remains challenging. To solve this, we need a partnership between global service providers and local digital nomad hubs with local services. The goal here should be to create a structure that goes beyond making it easy for someone to work from a location, but that also makes it easy to sustain the lifestyle. Here are the main things that need to be addressed.

• Movement between Nomad locations – perhaps through a Global Nomad Visa, which is accepted by Nomad zones worldwide.
• Tax considerations – perhaps through pro-rated taxes collected in each country based on the number of days the person was there.
• Housing – Additional housing for Nomads to help prevent both nomads and locals getting priced out when a location becomes popular.
• Safety Net – Nomads will get sick, and some will lose work for periods. This can be resolved by a global flexible insurance service for digital nomads.
• Retirement – Nomads often opt out of retirement savings because of the complexity of getting retirement savings in and out. This could be resolved by a portable, blockchain-powered retirement fund that offers automatic tax calculation, multi-currency contributions (including cryptocurrencies), and unified payout options across participating countries.
• Community – Nomads often leave the lifestlyle due to lonelinesss. This can be addressed through a combination of a global nomad community, integrated with structured local opportunities for nomads to connect with each other and the community.
• Childhood Education – perhaps through a Digital Nomad Hybrid School that combines online education with in person campus experience in digital nomad locations.
• Adult Learning and Development – focused on ensuring that the digital nomads themselves continuously work on the skills development that will keep their skills sharp

Question 5: How close are we to sustainable digital nomadism?

Possibly closer than you think. Several countries have developed Digital Nomad visas, and are modifying tax regulations to make them more digital nomad-friendly. Japan is building dedicated housing to support digital nomads. Outsite is building a network of coworking and co-living spaces in digital nomad hotspots worldwide. Safety Wing has developed an insurance product for Digital Nomads that covers both health and job insecurity. Fully online schools already exist, so the only remaining step here is to develop local integrated education hubs.

As for Adult Learning and Development – I think the model here is what’s happening in my current home town of Tulsa Oklahoma. As you may be aware, Tulsa is the home of Tulsa Remote, which provides financial incentives to people who relocate there. But in addition to those incentives, Tulsa Remote also provides access to one of the top co-working spaces in the US (called Gradient). But even better, Gradient provides programming designed to help people learn and grow while in Tulsa. My company is offering durable skills programming as part of this.

While Tulsa Remote is designed to encourage longer-term migration into Tulsa, this type of model could easily be used in digital nomad hubs. Once it is, digital nomads will be able to not only live the life they desire in the moment, but also lead a sustainable life as a nomad through retirement, one that allows them to learn and grow as individuals and contribute meaningfully to the places they reside.

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Huge thanks to Plumia, Safety Wing, and my fellow speakers and attendees for a great experience last week, and for giving me a new appreciation of Digital Nomadism, which is WAY more than Instagram influencers flogging their courses online. But a particularly big thank you to every friendly local I met in Marrakesh and Essaouira, who helped me see their country differently, and in doing so helped me see myself differently.

If you can…travel. It’s good for you.