Three questions to ask yourself before becoming a digital nomad

Living as a digital nomad is becoming more and more popular these days. Digital nomads, the location independent globetrotters who boast a never-ending insta-feed of exotic locales complete with friends of every nationality and a never ending supply of cool looking brunch pics, claimed to have found the ultimate lifestyle hack: working remotely and traveling indefinitely. They work when and where they want, for however long they need to, on projects that inspire them. Not limited to a single locale, they roam the world freely while accumulating the social currency of the modern age: experiences.

From the outside, this novel lifestyle looks extremely seductive. Even the most self-assured among you have probably questioned your life choices on seeing this glamorized portrayal of nomad life. You may have even gone so far as to download a free e-book, joined a newsletter, or taken a Udemy course all geared towards teaching you that you, yes even you, can, nay should, join the ranks of the global digital nomad tribe. But is it really that easy? Can anyone do it? Spoiler alert-no, but also yes, well it's complicated- keep reading to find out.

My take

Having lived as a digital nomad for a year and a bit, I am somewhat acquainted with the wonders and disappointments of nomad life. I’ve met many people living this lifestyle, some who are just checking it out and some who consider themselves seasoned nomads. In meeting these folks I have come to understand that this lifestyle really isn’t for everyone.

There are many challenges that most people who try nomading for the first time simply don’t anticipate. This is to be expected since we live at a time when people are encouraged to spend more time researching the ultimate travel backpack than to do a thorough self-inventory. However, the most essential travel must-have is self-awareness and that’s not something that you can order off Amazon.

I have compiled a list of three questions that you will need to ask yourself before entertaining the prospect of becoming a digital nomad.

1. How good are you at managing your time?

Most people are used to having a schedule created for them. From the time we enter kindergarten to the time we retire, our lives are dominated by the oppressive regularity of the 8-hour work day. While many find this way of living overly restrictive because it leaves little room for pursuing meaningful hobbies, relationships, and side businesses, the majority of those same people have not considered what their lives would be like if they could create their own schedule.
The truth is that balancing work and social commitments is a huge undertaking and most people overestimate their ability to do so. Many newly minted digital nomads swing for the fences, working either too much or too little. While the most highly anticipated part of living as a digital nomad is getting to see the world, many workaholic nomads find that once they are actually on the road, they don’t end up doing much beyond staying in their Airbnbs or co-working spaces and grinding it out. Others go broke because they lack the needed self-discipline to say ‘no’ to sightseeing and socializing instead of making money. Before you decide to go nomadic, ask yourself whether you are capable of managing your time effectively. In the end, this skill could make or break you as a digital nomad.

2)How good are you at making new friends?

Looking at the social media profiles of digital nomads, one would surmise that their lives are an endless buffet of meetups and parties. It is easy to forget that the images we see are all carefully curated to convey a sense of freedom, fun, and adventure. Many nomad entrepreneurs present their lives in this manner in order to get you to like and follow them on social media so they can eventually sell you their digital products. While it is true that there are many conferences, parties, and meetups in many digital nomad hubs, this one-sided portrayal of the nomad social scene is not all that it markets itself to be.

As much as nomadism affords you the opportunity to meet people from all around the globe, that’s all it is- meeting. Meeting someone doesn’t mean you cultivate meaningful connections much less lasting ones. Making real friends, finding your tribe, and building a community isn’t quite so straight forward. That’s not to say it can’t be done. I know of people who have been able to meet like-minded folks and start meaningful friendships, businesses, and romantic relationships. However, while this is theoretically possible, it requires effort, intentionality, and thick skin.

There is no blueprint to follow when it comes to making connections abroad. Socializing as a nomad means consistently putting yourself out there and that’s a skill that many people simply haven’t had to practice. Before making the leap out of the safe cocoon of your hometown take a moment to evaluate your social needs and assess the likelihood that those needs will be met when you are constantly traveling.

1. How good are you at having difficult conversations?

Traveling and working abroad is not for the faint of heart. Don’t buy into the glamorized portrayal of nomadism in the media. It is not as simple as buying a ticket. This lifestyle can and will test you physically and mentally in ways that you may not have anticipated. In order to survive and thrive in this new lifestyle, you need to be able to have difficult conversations with others as well as with yourself.

There will be conversations with your family who may not understand why you are doing this or support your decision. There will be conversations with friends who will be sad to part ways with you. There will be endless conversations with locals who will criticize your lack of cultural sensitivity. These are all hard in their own way but they all pale in comparison to the conversation you will need to have with yourself when you are lost in a foreign city and you have no one to call, or celebrating your birthday among strangers who barely know you, or in any other of a myriad situations that digital nomads find themselves in with startling regularity. In these difficult times, you will second guess yourself and doubt your choices. You may even experience the pangs of regret.

This is normal, all digital nomads, and just about every human I have known has and will go through this at one point or another. While people who follow a more traditional path can rely on their families, professional, and social networks for support and encouragement in times of crisis, digital nomads don't have the same luxuries.
In my view, the people who have successfully created a nomad lifestyle have done so because they cultivated a clear vision of what they wanted to get out of this lifestyle. It is this clarity that allowed them to persevere in the face of personal turmoil as well as societal pressure.

Final advice

Living and working as a digital nomad, just like every other path in life, has its highs and lows. Having done it myself, I believe that the majority of people considering this lifestyle have yet to contemplate the answers to the questions I posed in this article. If that's you. I hope this has been helpful.

Final Final words

If you are just looking for an easy path, look elsewhere. If you are running from something, it will find you. If you lack overall direction, being a nomad is unlikely to provide it for you. Nomadism isn’t a silver bullet or a lifestyle hack. It doesn’t solve your problems as much as it creates new ones. You need to ask yourself whether you have what it takes to solve them.

Ultimately, the most difficult and necessary question you need to ask yourself is why you want to do this in the first place? The answer might well prove its weight in gold. As Simon Sinek says, start with why.