Lessons Learned On Becoming a Digital Nomad
I became a digital nomad by accident. Fifteen years ago I worked in Boston for a small marketing agency that helped companies fill their sales pipelines mainly across North America. I was getting itchy feet and didn’t know what to do about it.Â
The growing markets across Asia, especially India and China, were no secret and so I started telling clients that we could also help them with their sales and marketing across that region. To my surprise, several clients said yes and next thing I knew I had to figure out how to deliver across these diverse markets. I never moved back to the US.
A lot of mistakes were made and lessons learned during this journey so I wrote a book about it. Below are a few of those lessons on how to become a digital nomad. These are two excerpts from my book.
In one of the last scenes in the original Ghostbusters movie, Dan Aykroyd’s character meekly approaches a vixen spirit. The spirit asks Aykroyd in a demonic voice if he is a god. Aykroyd looks at Bill Murray’s character, who nods and gives a little fist pump as if to say, “you got this.” Aykroyd replies quietly, “no.” The spirit answers: “Then die!” and zaps the Ghostbusters with lightning. As they recover, a third Ghostbuster played by Ernie Hudson declares, “When someone asks you if you are a god, you say YES!”
This advice is known as The Ghostbusters Principle. It’s another way of saying “fake it till you make it.” It’s a kind of overconfident optimism that suggests you’ll find a way to figure things out in real time or get fried trying. If one wants to become a digital nomad, this is an important skill to develop. Of course, there are limits to our omnipotence, so the trick is to find some type of balance that keeps things from getting out of control. When things do get out of control, which they inevitably will, it’s important to know how to roll with the punches. The Ghostbusters Principle is how I ended up starting my marketing agency out of an Asian brothel.
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Singapore is an island nation that is rated No. 1 in the world by the World Bank for its ease of doing business. From the moment you land in its airport you can tell it is a friendly place. I mean, the airport is home to the world’s largest indoor waterfall and this sets the stage for the rest of the island’s state-of-the-art infrastructure. The skyline looks like the future. A bright, clean, safe future. It’s an oasis for the modern digital nomad.
I thought about these things while sitting in my “hotel” that I had recently learned, rented rooms by the hour. This sort of guesthouse didn’t offer internet access, but I found a nearby unsecured wifi connection that kept me going through the night. This was yet another Skype call with a client from the United States who didn’t seem to understand time zones and the fact that it was 1 a.m. here. She was talking about her cat. Hopefully the noise-cancelling headphones did their job because these walls were thin. I thought about my housing situation—the plastic sheets, the super-cheap rates, the geckos zig-zagging across the walls catching bugs, and the small, dirty window that looked out at the side of a grungy building.
This was not the adventure I had thought I was getting into, and I was quickly learning that many things in the global business world were not what they seemed. But I had made my plastic-covered bed, and I was determined to lie in it.
This project epitomized the new world of globalization. A tech giant outsourced a critical piece of marketing and sales to an agency who outsourced it to me. I then outsourced it to someone else, while running nightly team calls with dozens of “executives” hoping they couldn’t hear my noisy neighbours. There were more people managing this tenuous supply chain than doing any of the work.
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In fragmented situations like these, finding opportunities was not too difficult. In business, any time there is a gap, an uncertainty, there exists opportunities for some enterprising entrepreneur to figure out how to bridge the gap. When nobody knows how to bridge a gap, it is up to those of us willing to face the unknown, take the risk by facing our demons and, at some point, simply saying, “yes.”
The agency in the United States that hired me was a publicly traded company. They already updated their website announcing they had a new APAC office in Singapore. That was me. On a Skype call. Pirating wifi while sitting on a plastic sheet whose history I dared not contemplate. It seemed there were a lot of us applying The Ghostbuster Principle.
I was one small part of this problem because I kept saying yes to anyone wanting to enter these markets. When it comes to getting into the global game, yes, go for it, but be careful what you promise. At this point of my adventure, I had created an illusion of competency and convinced my clients I understood what was going on in these foreign markets. I had positioned myself as the one who could overcome these obstacles and accelerate growth. Now, I had to deliver, and that brings me to the second important lesson for becoming a digital nomad.  Be accountable.
Digital Nomads live and die by how they hold themselves accountable for everything they promise (and overpromise) their clients. Accountability means no excuses, and this is difficult because something always goes wrong. From faulty internet connections to man-made or natural disasters, the buck stops here. How these daily obstacles get overcome is part of the fun so long as you have the right attitude.
It took me a number of years to learn these lessons. This new era of globalization will need people who know how to use the Ghostbuster Principle, who understand the importance of doing their homework and who are consistently accountable. It sounds easy, but it is not.
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We may be heading into the era of digital nomads, but be warned, it’s not all rainbows and airport waterfalls.
5 must-have skills to be a digital nomad
Over the years, hundreds of projects gave me insights into business expansion plans. Some were flimsy, quick-hit approaches, some were well-thought-out frameworks, and others were spend-whatever-it-takes strategies. They all took unexpected twists and turns, but within all the plans there was one consistent variable that kept everyone off-balance: people.
Globalizing business was no longer just about giant cargo ships moving goods from one place to the other, it had gone human. Everyone was trying to figure out who they were suddenly working with across the planet. Who they were selling to? Who they were collaborating with? Who were their new colleagues? And everyone shared the same assumption that things would be business as usual, but usual according to whom?
Over the years I have put together a few tools to help digital business nomads as they go global. I call it The Global Survival Kit. Below are some of the tools to help you along your journey. Many of the origins of these tools came from the people I’ve met and situations I’ve been through. And hopefully it won’t surprise you that it is constantly changing and adapting. Enjoy!
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1. Know yourself
Research continues to come out showing strong leaders have higher-than-average levels of self-awareness.
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No one is perfect, so the need to understand strengths and weaknesses makes for an important first step in improving how you work with people across the globe. Hierarchies and various cultures around the globe make this one especially tricky. How do you show vulnerability in a part of the world where that is looked down on? How do you admit when you are wrong within a surrounding that punishes weakness? You have to first know yourself. Behavioral psychology assessments can be a good place to start.
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2. Cross-cultural data
 These issues are not new. Five hundred years ago, Magellan and his shipmates landed on islands across the south pacific, and local tribes would come on board ships and start taking trinkets and anything that wasn’t bolted down. They were coming from a collectivist culture where the concept of individual ownership did not exist. Their actions were interpreted by the significantly more individualistic Europeans as stealing. Situations escalated quickly, from yelling to pushing to weapons being drawn. People died, including Magellan, who never made it past the Philippines.
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I’d argue that half a millennium later, we have not really progressed that much. Today cultures cross paths daily, with the purpose of building business ties and doing deals. While most interactions tend to work out well, work situations, as we have seen, can quickly spin out of control. From start-ups to world leaders, these issues can cost money and sometimes lives.
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There is hope! There is data. Differences across cultures have been defined and continue to get measured. If you can measure it, you can manage it. At least that’s the idea. While these datasets are far from perfect, they can be a great resource to better understand different working styles and how to adjust to interactions around the world.
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3. Learn to adjust in a moment of panic
 From being unable to order a cup of hot water to negotiating multimillion-dollar global contracts, we all get those screaming on the inside If you know one of these moments is happening, PAUSE.
Pause. Are you screaming on the inside? You aren’t alone. Take a breath. When working through foreign situations, often gut responses can be wrong. So, before anything is said, pause.
Active Listening. This may be the single easiest and yet most important tool to manage people, excel in sales, find a mate, handle networking events, negotiate, etc. And it is absolutely critical when communicating across cultures.
Use cross-cultural data. With big-data flooding in from internet use around the world, expect a lot more research from this field in the coming years. The datasets we use today will look archaic within the decade, but for the time being, they can be of great help to better understand cross-cultural differences.
See things from the other person’s perspective. This is easy to say, but hard to do. There are ways we can practice and improve how to see situations from different angles.
Elaborate. Possibly the easiest but least used approach for any conversation. Before allowing a conversation to end, double check the next steps or the key point made. Simple wrap up statements include: “Before we end, can we quickly summarize the key points and next steps?” or “Can you feed back to me what you heard?” or “What is the specific next step here, and when will we reconnect to look at progress?”
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4. Communication Contracts
 Do not be lulled into a false sense of security because you have crystal clear phone or video connection. Great communication technology is not the same thing as great communication. Great digital nomads clarify ideas, instructions and next steps often. The simplest words can be the hardest, yes, no, trust, respect, openness, etc. In fact, they can mean very different things to different people. Invest time with teammates and clients to lay out communication rules. Establishing guidelines early will reduce misunderstandings.
A strong communications contract should be a part of any digital nomad’s toolbox. Ideally this agreement should be created as a group so everyone understands the purpose and everyone has a say. You may be surprised at where the conversations lead. This is a good thing. Get the surprises out early and get the fundamentals out in the open early.
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5. Share stories with friends
In a majority of workshops I run, the first activity is to hear from the participants about cross-cultural challenges they have faced. The rooms start out quiet. So, I share one of the many stories I’ve picked up or been a part of. It could be a small moment trying to get directions or something much larger.
A funny thing happens. Another person speaks up with a story. Then another, and another. Frequently, these issues, these frustrations have never been shared.
Maybe people are concerned about sounding insensitive or maybe they are embarrassed and don’t want to sound silly. But you can feel the energy in the room rise along with a sense of relief. Finding others who wrestle with these common international issues feels good. It builds connections and often, friendships. We discover that most of us mean well even though we are frequently misunderstood.
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We want to figure this stuff out. We want to understand differences and we want to be understood by those we work with. But often organizations and teams hide these culture clashes or ignore them. The stories get buried, erased, or forgotten. We don’t learn from our past mistakes and we miss opportunities to make new connections. This has perhaps been the most surprising finding from my work. The hesitation or, in many cases, deliberate actions to erase the past. I would love to say that companies have become better at going global since I started my own journey back in the first years of the twenty-first century. I have not seen much evidence for this. The best Digital Nomads are those who know how to share stories that build connections and drive clarity to business situations. So, tell your stories and learn from others! Good luck and enjoy the trip!
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Kyle Hegarty helps organizations grow globally and he has lost count of how many countries he has worked in. His sales training programs help clients increase business across regions and his global communications programs help strengthen teams, build trust, and prepare next-gen leaders for tomorrow’s threats and opportunities.
 His first book, The Accidental Business Nomad: A Survival Guide for Working Across a Shrinking Planet came out this summer
