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Remote Work Lifestyle

FAQ: What can you do to get a remote job that allows you to become a digital nomad?

Want to go fully remote on the road (or in the sky, or by the beach)? Here's how to land a remote job that supports the digital nomad life.

7 mins read time
Jeanna Barrett
Jeanna Barrett

Aug 08, 2021

We all know what we see on Instagram isn't exactly real life. It's carefully curated, precisely posed, and expertly filtered to make followers just a little bit envious. Technically real life, just seen through a gauzy curtain of perfection.

But what if it wasn't? What if those sweeping panoramas of sunsets on the beach or cozy snaps curled up by a blazing fire were genuine, authentic glimpses into the lives of people living their work-from-anywhere dreams?

What if we told you they are real, and they could reflect your own WFA life, too?

Look, we get it. Reality can be...jarring. The last couple years have been brutally, painfully real, which is probably why you're dreaming of working from a remote mountainside cabin, and not on the other side of the mountain of laundry on your bed.

You can have an Instagram-ready life as a digital nomad. If 2020 proved anything (aside from the fact that Americans use too much toilet paper), it's that working remote is not only possible, it's productive, and for some companies, it's preferred.

Digital nomadism was on the rise long before 2020, and the momentum isn't slowing.


digital nomad growth


You just have to know the right questions to ask. Here, we've compiled some of the questions you should be asking if you're looking for remote work that will allow you to become a digital nomad and start living the life you've only seen in pictures.


What Are the Best Jobs for Digital Nomads?

The best way to find a digital nomad-friendly job is to find a company that supports the work-from-anywhere lifestyle. Prior to 2020, that often meant digital nomads were free agents, working for themselves. They had plenty of freedom to travel but often lacked the stability of a full-time gig. Now, more companies realize their remote workers can get the job done wherever they are, and offering the ability to work remote is a pretty sweet job perk that allows them to recruit top talent.

So, if you're searching for a remote job that allows you to travel, what industries and roles offer the most flexibility?

  • Telework: If you have a phone with a good signal, you can work as a customer service representative or a sales agent from almost anywhere.
  • Online Jobs: Computer programming, data entry, coding, transcription, and medical billing require little more than a laptop and reliable Wi-Fi.
  • Skilled Jobs: Have a background in a certain field? Finding a job as a graphic designer, copywriter, online tutor, or web developer could be a great fit.

Where Do I Find Remote Job Opportunities?

If you want the flexibility of the digital nomad life with the stability of a traditional full-time job, you want to look for a fully distributed company that invests in remote employee culture. Today, there are many sites that specialize in remote job listings and are a great place to begin your search.

  • FlexJobs: This trusted site is the leader in remote job opportunities. They thoroughly vet every listing, so you know you're applying for verified remote positions.
  • We Work Remotely: The world's largest remote work community (self-described), this site has job listings from top companies around the globe.
  • Working Nomads: Specially designed for digital nomads, when you apply for a job via this site, you know you're applying to a company that truly understands the WFA lifestyle and will support your goals.
  • Upwork: If you aren't finding a more traditional job to launch your digital nomad adventures, you may want to test the freelance waters. Upwork is a great place to find jobs that match your skills and interests and could be a great trial run for full-time WFA living.

Will My Remote Employer Understand My Digital Nomad Lifestyle?

Fully distributed companies usually get it, but not all are on-board with globetrotting employees. Some may want you available during normal office hours in their time zone, and some may worry about your productivity if you're working while traveling. Here are some questions to ask prospective employers to find out if they'll support a digital nomad lifestyle:

  • What hours do I need to be accessible and available for meetings?
  • Can I work outside "normal" business hours as long as my work is done and done well?
  • What are your expectations for employees' workdays? Do you support asynchronous work schedules?
  • How do you communicate with employees when they aren't working from home? Do you have tools or apps you use for communication across locations and time zones?
  • How much autonomy do your employees have? Do you have a "butts in seats" mentality?

What Can I Do to Increase My Chances of Getting a Digital Nomad-Friendly Remote Job?

There are many ways to improve the odds of landing your dream remote job, but the proof will always be in the work you do. If you're consistent with meeting deadlines, show up for virtual meetings prepared and engaged, and ensure the quality of your work is never impacted by your travel schedule, you're in a great position.

If you haven't already, start honing a work-from-anywhere routine that helps you maintain productivity and improve your work/life balance. Ask for endorsements on LinkedIn that reflect your dedication, timeliness, and flexibility. Communicate clearly and often so potential employers know that you won't go off the grid in the midst of a major project.


How Will I Manage Work and Travel If I Haven't Done It Before?

There's a first time for everything, right? It's normal to be nervous when exploring the unknown, but you can set yourself up for success. Our tips on working while traveling are a good start.

You might be thinking you're too inexperienced to become a digital nomad, or too old, but you'd be wrong. Digital nomads defy labels. They come from all generations, all levels of experience, and all backgrounds.


how old are digital nomads



What Characteristics Should I Look for on My Job Hunt?

First, you want to find a company that understands digital nomads and supports the lifestyle with flexible work and the tools and resources to make it possible. Look for companies that use instant messaging tools like Slack and project management tools like Asana to make sure all employees are on the same page, no matter where they're working from.

Also, look for companies that value quality over quantity when it comes to the work you do. Digital nomads work a lot of hours (often at unusual times), but they're no match for their traditional counterparts.


graph comparing how much digital nomads work to traditional jobs



How Do I Get Started on My Digital Nomad Job Hunt?

It sounds cliché, but the best advice is to stop thinking and start doing. Use the sites listed above to search for jobs that fit your skills and experience and start applying. Do some research on working while traveling, the best countries for digital nomads, and how to stay productive while working on the go.

Oh, and remember to snap a few pics wherever your work, and the wind, takes you. After all, real life isn't like Instagram. It's even better.

Want to get more out of remote work?  Listen to our Remotely Cultured podcast, full of tips and tools to live and  work your best from anywhere.  Listen Now

Jeanna Barrett

Jeanna is the Founder & Chief Remote Officer for First Page Strategy, an award-winning, fully distributed marketing agency. Jeanna has a combined 17 years of inbound marketing experience at venture-backed startups, digital agencies and Fortune 500 companies, with an expertise focus on business and tech. She's been named 'Top 40 Under 40' of brand marketers and 'Best in the West' for financial technology marketing. In 2016, Jeanna left the U.S. to lay roots and build her business in Belize, and in 2021 First Page was named #43 in fastest growing private companies of Inc. 5,00 Regionals: California.

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