Here are some uncomfortable questions you will face in your life and travels as a digital nomad. And some potential answers.

Where are you from?

“I am originally from London, but I’ve been living in Buenos Aires for the last three years and now I’m transitioning to Shanghai.”

This question and answer was typical of the introductions that took place among a group of nomadic workers I met at a retreat on a beautiful Croatian island. Among the many conversations we had, one of the most interesting and humourous ones was about the most annoying or difficult questions that nomads face from family, friends, and even absolute strangers!

As I spent the last few days working and meeting people on the island, I reflected on all the questions or assumptions thrown at digital nomads (and ones I’ve personally experienced).

What do you do?

This one is a natural (and very popular) question but it can be complex to answer. But my favourite answer to this is: “I am a serial gig worker, working on different projects, across different places.” Chances are you will have to explain what gig work is, but this always leads to an entertaining conversation! My favourite answer from another nomadic friend is: “I travel, and work when I have the time.”

When will you settle down?

This question is guaranteed to set a nomad’s teeth on edge. However, it is based on the assumption that there is one way to live and that while we may indulge in our little adventures, in the end everyone must finally settle down into a “responsible”, stable life in one place with a respectable long-term job. Different people deal with this question differently. The way I’ve dealt with this question is to try and explain my paradigm of living and working and instead of getting defensive, to try and get the questioner curious and engaged.

How will you hold down a long term relationship?

This one is a valid one and in truth, many nomads find themselves starting and ending relationships when they move. Long distance relationships, though doable, are notoriously hard to sustain. But as one nomad succinctly put it: “I’m in a long term relationship with myself!” The digital nomad journey is often about self-discovery, learning and growth, and people on this path, while still needing relationships, also derive a sense of deep meaning and fulfilment in their own evolution and many transformations.

Read other posts from the Digital Nomad series

How will you make money?

Granted the nomadic way is not the easiest way to a McMansion and the Audi R8, but as many nomads, and especially Millennial nomads, will attest, one of the reasons they choose this lifestyle is because they already subscribe to a different value system and different set of priorities. Making a lot of money may or may not be a part of that.

Also, nomadism is sometimes seen as a synonym for vagabonding, or a refusal to take responsibility. Apart from the fact that many nomads have built successful companies or are self-sustaining, the deeper subtext of this question may also point to the idea of making money as an end in itself, whereas many nomads see money as a freedom provider and something that allows them to live on their own terms.

While you will encounter some of these questions regularly, it helps to remember that it requires a paradigm shift over time for many people to see things in a different light. If you find that family or people you care about are struggling to understand or accept your decisions, then gifting them a copy of Tim Ferriss’ The Four Hour workweek or Chris Guillebeau’s The Art of Non-Conformity may be a good start.

In the end though, a lot of this will come down to your own ability to stay true to yourself and be confident in your choices. The ability to be comfortable with a lack of understanding of your chosen lifestyle is something that emerges slowly, with time and awareness. And one day, you wake up and realise that you are living a life that you is truly and authentically yours, and that’s all that really matters.

“Confidence is knowing who you are and not changing it a bit because of someone’s version of reality is not your reality.”
― Shannon L Alder

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