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Digital Nomad Lifestyle: What It’s Really Like, from a Millennial Living It

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In “Generational Remote Work Statistics: How Millennials, Gen-Xers, and Baby Boomers Telework,” a Virtual Vocations report on the work preferences and job search tendencies of professionals across a variety of age groups, 87% of Millennials and 84% of Baby Boomers said they are interested in the digital nomad lifestyle or learning more about it.

Eric Schad, Virtual Vocations contributor, shares his experience of living a digital nomad lifestyle and details what it’s really like to continuously work remotely and travel outside the U.S.

Digital Nomad Lifestyle: What It’s Really Like, from a Millennial Living It

Perusing social media, it’s become all too normal to see images of an open laptop set among palm trees, with crystal-clear waters in the background of some far-off destination. A caption reading “My office for the day!” piques your interest. Now that is living, you think as you sip your $5 cup of Starbucks and get ready to brave harsh winter weather. The thought of the digital nomad lifestyle fades from your mind, only to reappear again and again during your daily Instagram browsing.

Maybe I could really do this—but where, and how, do I even begin?

There’s no straightforward path to begin your global tour as a digital nomad. But, before you give up your traditional job with full benefits, a steady paycheck, and paid vacation, you have to weigh the pros and the cons, the upsides and the downsides, and the awesome and the overrated.

The digital nomad lifestyle may be the perfect life for some, but don’t be fooled by the rose-colored, social media glasses—there’s no way to understand what it’s truly like until you’re there.

So, just in case you were wondering, here’s what it’s really like to live the digital nomad lifestyle.

Full-Time vs. Freelance Remote Job Prospects

The state of remote work

The good news from the front lines is that remote job prospects are at an all-time high. Around 43 percent of Americans work a portion of their week away from the office, while 63 percent of companies have remote employees. There are plenty of telecommute and flexible jobs out there, but what situation will fit you best?

Evaluating your current job in relation to telecommuting

If you believe that your current job is easy to accomplish remotely, becoming a digital nomad might be an interesting prospect. You’ll need to pitch the idea to your employer, but if they’re on board, you won’t have to give up your vacation days, health insurance, and retirement plan. This trifecta of benefits looks better and better every day to many digital nomads, so if you can keep it, do so.

The crux of the matter here is being realistic. If you’re working 50 or 60 hours a week at a salaried job, is it really in your best interests to gallivant across the world? Would you really get to see anything? Or would it just complicate your situation? Those are questions that only you can answer.

What if you have to get a new job?

If your current position doesn’t translate to the digital nomad lifestyle, don’t fret. You still have plenty of other options for full-time employment. Many companies have 100 percent remote jobs that might fit your experience or expertise. Applying to as many as possible before you make the jump to nomad can help you gain confidence, improve your cover letter, and allow you to learn the job market demand for your particular skill set.

While there are employee positions available, freelancers and entrepreneurs seem to dominate the digital nomad landscape. Some of them are trust-fund kids; others got lucky in the Bitcoin craze; but many just saved up cash, found something they either loved or were good at, and hit the road. Perhaps most inspiring are the nomads who turn their passions into a career and become writers, programmers, and teachers, among others.

The category of digital nomad you fall into is irrelevant; the lesson is, if you’re going to travel extensively, you may as well find something that rekindles your passion for work—or at least will keep you afloat for as long as possible.

digital nomad lifestyle - Virtual Vocations remote and flexible jobs

“But I Have No Marketable Skills or Experience” (or So You Say)

Overcoming negative thoughts

The idea that you don’t have the skills or experience to become a digital nomad is a common thought. It’s deep in both your subconscious as self-doubt, and in the words of people you love who are just “looking out for you.” Don’t listen to either.

I’m not going to tell you that you’re unequivocally the greatest in a particular field, but I will say that every person has some type of skill that makes them unique or is prized in the marketplace. However, it does take some soul-searching to identify those skills.

If I can do it, so can you

When I graduated from university with a double major in finance and music, I was thinking to combine a passion with something practical. Although I didn’t know it at the time, this intersection of enthusiasm, talent, and pragmatism is the ideal fit for a digital nomad. As I write this article from the foothills of the Southern Alps in New Zealand, I never dreamed that my random background, jack-of-all-trades resume, and sheer desire for something new would take me down this path. But here I am.

I’m a digital nomad telling you it’s possible if you apply yourself. Open up your mind to all the prospects available, and you might be surprised by what remote jobs you find and how much you enjoy them.

I can’t tell you how many writers, yoga teachers, bartenders, coders, IT pros, and other people I’ve met who made the transition to the digital nomad lifestyle. Now that they’ve done it, they wouldn’t have it any other way.

The Upsides of the Digital Nomad Lifestyle

Human connections

Ubiquitous and romanticized Instagram posts aside, the digital nomad lifestyle has an alluring and exciting side you can’t find anywhere else (unless you’re a circus performer or a roadie for Metallica or something to that effect).

You can travel with reckless abandon and explore the far corners of the world, soak up exotic cultures and sample the tastiest (or grossest) foods imaginable, and interact with people across the globe and enjoy the simplest of connections: the fact that we’re all human.

While ancient relics in Europe, giant stupas in India, and 50-cent beers in Southeast Asia all have their appeal, it’s the human factor that makes the ride even more worthwhile. Working solely from home, you’ll never have the opportunity to meet a programmer from Slovakia, a chef from Argentina, a guy on sabbatical from Los Angeles, and a marketing consultant from Japan—all in one room.

That’s the hidden treasure of becoming a digital nomad.

The conversations and experiences that stick with you for a lifetime, while also furthering your potential job prospects and partnerships through networking. And don’t forget about the locals, who are always excited to meet new people from abroad (and who also give you the low-down on the area’s best-kept secrets).

Professional and personal independence

Another upside to becoming a digital nomad is the freedom it brings. When you’re bored with a city or you want some fresh scenery, you can move. And not just for a few days or a week-long vacation—you can stay indefinitely (or until your visa runs out).

Have you always wanted to live in Paris? London? Sydney? Bangkok? Now you can do it all in one year. There’s something to be said about a job that allows that type of exotic flexibility.

Building upon freedom of location is the freedom to create your own position as a consultant, freelancer, or contractor. You can create your own niche. The world is yours for the taking.

The Downsides of the Digital Nomade Lifestyle

As with anything in life, not everything about the digital nomad lifestyle is sunshine and lollipops—even if it appears that way online. Yet, it’s surprisingly difficult to figure out if you’ll love being a digital nomad without actually diving into it. There are many pitfalls and undisclosed aspects that can derail fledgling digital nomads before they really take off. 


The first thing to ask yourself is if you’re a bit of a loner, because you’ll need to be. Unless you can find a work or life partner who’s willing to join you on your journey, you’re headed out on your first flight solo. If you enjoy going to the movies by yourself, taking walks by yourself, or just genuinely enjoy alone time, you’ll probably be alright. However, if you’re someone who waits in your car until your friends show up after arriving early to a restaurant, the digital nomad lifestyle probably isn’t best for your future.

Even if you’re just fine on your own, being a digital nomad can get lonely. Maybe not in the sense feeling alone in the universe, but you might come across these related emotions: the fear of missing out (FOMO) on what’s going on at home, the fear of no one to share experiences with, or a lack of connections with the people you meet. This doesn’t happen to everyone all of the time, but it happens to everyone some of the time.

Financial insecurity

Where does money fall on your values scale? Money isn’t everything, as the old saying goes, but it sure makes life a whole lot easier and gives you the ability to purchase the niceties in life. When you’re a digital nomad, you might have to say goodbye to the comfort of steady paychecks and upscale items. You’ll also have to pay for insurance and plan for retirement on your own, so you may need to start channeling your inner Warren Buffet before you leave.

Succeeding as a digital nomad is all about rolling with the punches and breaking out of your routines. 

If you’re used to pampering yourself with a daily no-whip-low-fat-soy-milk latte and buying the latest gadgets and clothes, the digital nomad lifestyle is not for you. digital nomad lifestyle - Virtual Vocations remote and flexible jobs

The Terrifying Realities of the Internet Situation (and How to Overcome Them)

By far the most difficult aspect of the digital nomad lifestyle is finding reliable Internet. Some places have surprisingly reliable Internet and Wi-Fi for free, while it’s non-existent in other locations. If you’re ever in doubt, look for the golden arches. McDonald’s has saved me the embarrassment of missing a deadline more than a few times.

Globally, the availability of the Internet is always improving. According to the World Bank, nearly half the world’s population now has access to the Internet. That may not seem like much, but it covers most of the places you’ll want to visit. Telecom companies also have plans which allow unlimited data for hot-spotting your computer when the Wi-Fi situation gets tough.

For a backup plan, buy a pocket Wi-Fi that can connect to the Internet via satellite from almost anywhere in the world.

What I Wish I Had Known About the Digital Nomad Lifestyle

While living as a digital nomad can be an invigorating and life-changing experience, it will also test you. Here are two things from my own experience that I wish I knew before adopting the digital nomad lifestyle:

1. If you’re choosing the digital nomad lifestyle to run away from something, it’s probably not going to work

Zipping overseas as a digital nomad because of a break-up or a layoff isn’t going to end well. You must be clear-headed to make good decisions. Otherwise, factors like fear and resentment will drive you to a breaking point.

2. Have faith in yourself

This isn’t to say you should throw your inhibitions to the wind or have unrealistic expectations. But if you are brave enough to entertain the digital nomad lifestyle, chances are you have the self-motivation to succeed as a remote employee or freelancer.

The digital nomad lifestyle is glorious, terrifying, enthralling, and delightful all at once. It gives you professional and personal control and flexibility. It allows you to take the reins.

If you also think the digital nomad lifestyle is for you, hold tightly to those reins; it’s going to be one wild ride.

Are you intrigued by the digital nomad lifestyle or do you currently work and travel abroad? Connect with Virtual Vocations on Facebook, Twitter, and LinkedIn to tell us your thoughts on the digital nomad lifestyle. We’d love to hear from you!

iStock Photo Credit: 1. RoBeDeRo; 2. monkeybusinessimages ; 3. GenerationClash

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