Becoming a Digital Nomad: the Good, the Bad, and the Ugly

My first job out of college was as an English instructor for an education center in Hong Kong. A year later, when it came time for me to leave, my boss proposed that I continue working for her, remotely.

That’s how I stumbled into the digital nomad lifestyle — by writing curriculum for my employer in Hong Kong while backpacking around India and China. I’ve never looked back.

And I’m not alone — digital nomadism is the new normal. As soon as the technology became available, people like me packed their bags and took their work on the road. With an increasing number of communication channels like Skype and Slack and flexible payment options like Gusto and Paypal, the digital nomad movement has only continued to gain steam.

But there’s more than one way to become a digital nomad. If you’re interested in launching a career as an entrepreneur on the road or want to find that remote job of your dreams, here are some tips to get you started.

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Getting started as a digital nomad

Digital nomads typically fall into two camps: either freelancers and entrepreneurs, or remote workers and telecommuters. The main difference is that freelancers and entrepreneurs run their own businesses while remote workers and telecommuters are employees for a company.

The benefits of being a freelancer or entrepreneur are that you can truly make your own hours and choose the work you want to do. The flipside is potentially unsteady income and the constant hustle of finding new clients.

As a remote worker or telecommuter, you have a stable income and the flexibility to travel. On the other hand, you need to contend with the potential for a toxic work environment, unreliable coworkers, and being tied to goals set by the company rather than yourself.

I freelanced from 2011 to 2015 and burned out from the constant strain of maintaining a solid base of paying customers. There was an unpredictability I found profoundly uncomfortable, which is why I sought out full-time remote work. Regardless of which path you choose or if you shift from one to the other, there will always be a trade-off. You just need to know what you’re most comfortable with.

Tips for finding work as a digital nomad

1. Build a portfolio

Have something down on paper, especially when you’re just starting out. If you’re a writer, start a blog. If you’re a developer, showcase your creative coding skills. If you’re a designer, have an eye-catching website. This will give you a starting point for showcasing your skills as you build up your experience. A portfolio also helps you establish authority in your field.

2. Ask for referrals

Once you’ve built up experience, ask for referrals and make sure to get testimonials. Ideally you’ll want to build a set of repeat customers.

3. Leverage your network

Reach out to friends or acquaintances who work in your field and see what shakes out. You never know until you try!

4. Just start

Get out there and start applying, sending cold emails, and even reaching out on social media. Make a list of potential clients or publications that you’d like to work with and go wild.

5. Demonstrate reliability

Deliver on your promises, understand time zones, and present a professional appearance during video interviews. It’s cool to dress in pajama bottoms, as long as you have on a respectable shirt!

You don’t need to be a programmer to be a digital nomad

Scroll through any remote job site like We Work Remotely or Remote OK and you’ll find jobs that typically fall into four categories: software development, design, writing, and customer service. In the past, software developers reigned supreme when it came to remote work and digital nomad opportunities. Luckily for the rest of us, that trend has shifted and now you can work pretty much any profession on the road.

If you’re looking for remote-only companies to help you with your digital nomad dream, take a look at FlexJobs’ comprehensive list.

What I wish I’d known before becoming a digital nomad

A lot of hype surrounds digital nomadism. Michael Thomas said in Quartz that “The promise of the idea was captured in a common slogan: ‘Get paid to travel the world.’” But it’s not as easy as packing your laptop and booking an Airbnb.

1. It’s hard to convince people you’re actually working

If it looks like a vacation and acts like work, then it’s a digital nomad career. Let’s be honest: There’s something to be said for cultivating that Instagram persona, but you might be shooting yourself in the foot. Perception is a beast, and it’s often unfair. You know you’re working 40+ hours a week in a cramped hotel room with little time to sightsee, but it’s hard to receive empathy when it seems like you’re living it up. Be prepared to burst some envious bubbles of what your day-to-day is actually like.

2. Your internet connection

In the words of Kristi Thompson, customer service champion at Help Scout: “I was under a constant low level of stress worrying about my internet connection.” While she was digital nomading across the U.S. and in Argentina, Costa Rica, France, and Austria, she learned to work near or in coworking spaces with stable internet access. I used to strategically book specific hotel rooms in Lhasa, TAR, that I knew had the strongest WiFi signals. When I was in Dharamsala, India, there would be days with 16 hours of no power. If I had a project due, I was sweating bullets waiting for the power to flicker back on with my finger ready to click send. It was valuable to learn to always work ahead.

3. Set boundaries

For a digital nomad who is quite a few time zones away from your manager, it can be easy to overwork. Whether it’s waking up for meetings at 4 a.m. or giving presentations at 11 p.m., it’s hard to know when you’re off the clock. Other professions should take a page from customer service representatives who have set hours for when they’re on call. Be intentional about establishing clear guidelines for when coworkers can schedule you so you don’t end up with 2 a.m. one-on-ones!

4. Know your budget

This is a basic life skill, but especially when you’re dealing with flights, new accommodations, and changing currencies, it’s important to have set finances. If you’re a freelancer on the road, you need to know how many clients are required to fund your traveling lifestyle. If you’re a remote worker, make sure you know how long payments take to deposit in your bank and when funds will be available. It’s also important to note the norms for how different countries accept payments be they cash, check, or card.

The ins and outs of life as a digital nomad

As with everything in life and career, working as a digital nomad is multifaceted. Here's a breakdown of what I consider the good, the bad, and the ugly of pursuing a remote profession on the go.

Take this show on the road!

Digital nomads come in all shapes and sizes. You can travel every week or you can choose a home base and stick around in one country for a longer period of time. When I burned out on the one-to-three-month pattern, I lived in Alanya, Turkey for a year because I could meet their residency requirements. This was a great base that I used to travel to around the region, but I still felt like I had a home.

You also don’t have to be a full-time digital nomad! Right now I split my time between living in Florida and traveling in the winter and summer months to Hong Kong, Washington, D.C., and even Iceland.

Being a digital nomad isn’t for everyone, but the future of work looks to be majority remote. If you can make it work, you’ll never look at the office the same way again.