How to work and travel as a digital nomad

I would bet money on the fact that you spend some of your workday daydreaming about your next vacation. I used to do it all the time, and if you were to look over my shoulder in the newsroom, you could usually find me clicking around Google Maps at random for travel inspiration. 

I ultimately quit my job to travel, but what I learned after that was unexpected: I was actually able to rebuild my career in a new way, using my same skills, so I could work and travel the world at the same time. Welcome to the world of being a digital nomad. It’s not a hat I ever saw myself wearing in real life..

Here’s the thing: it used to be that if you wanted to travel long term, you had to quit your job. And of course, there are plenty of people who want to travel the world, who are also nervous to step away from their careers. This was me. I was ridiculously attached to my career and deeply believed in my work (I still feel that way about news).

Disclaimer: I do think quitting work to travel is an excellent idea for some people, and I myself did it. But it’s definitely not a one-size-fits-all approach to traveling the world.

So here’s what I’ve discovered: you can actually travel the world, long-term, without quitting your job and rattling future career prospects. The trick is to find remote work in your field. And here’s the good news: more people are working remotely now than ever before, and the growth is pretty impressive. The amount of people working remote at least some of the time has basically quadrupled over the past decade. What does that mean? It means that becoming a digital nomad is much easier than you think, because there are a lot of remote work opportunities.

Let’s dive in.

The three methods

There are three methods to becoming a digital nomad. I’ve made them up, so you could either consider them “imaginary” or “proprietary” (I prefer the latter).

• The first is to stay in your current job and continue to work it remotely 100% of the time (for the period of time that you’re traveling).
• The second is to find a new job in your field, or in an adjacent field.
• The third is to find any remote work online in a new field.

Let’s take a closer look at the pros and cons of each method.

Keeping your current job

You probably already know if this is an option for you. Some offices and roles have the capabilities of working 100% remotely. My job in television news was not like this, but I want to give this option some space here.

If you work for a company, whether full time or part time, you are deeply committed to the work, and you can work the role 100% remotely, this may mean it’s an excellent idea to stay in your role while traveling. You get to do work you love, in a role you already know, while budget traveling the world.

Here are the potential challenges: it can be unrealistic if you need to be around for certain working hours while shifting time zones, or if you need to occasionally go into the office. Plus, not every company is okay with having an employee become 100% remote. 

My advice if you’re considering this? Float the idea of working 100% remote by your bosses, and see how it lands. It may be the case that if you just ask, the answer will be yes. It may also be possible for a set period of time, say two or three months, which would enable you to travel while working during that time. It may mean you have to get used to a new workflow, but that’s kind of the case anyway, if you’d like to work while traveling the world.

Find a new job in your field, or an adjacent field

This option is my favorite because it’s what I did, but it’s also what I was forced to do.

I want to start with one question: do you want to work in your current job until you die? Forgive me for bringing the drama, but I’m really serious. Because if your current job is a role you’re going to move on from at some point in your life, then I think changing roles to travel is totally within your framework for success.

 It’s not at all a negative to “quit,” and there’s a big stigma around “quitting.” But in reality, you’re moving on to a new role, as you would be at some time along the line anyway.

How can you find a remote job in your area of expertise? It’s entirely possible to find remote work in almost all fields, as I broke down in this post. But what if your job isn’t one that you can find remote opportunities in? Hi, that was me again 👋 

That’s when we start looking at adjacent fields. These are careers which utilize your skills and your specialties, which you may have never considered before. The great thing is that while working in these fields, you’ll still have a full resume and be nurturing your career, because the skills are similar.

Here’s my case study: I was working in TV news, a job I couldn’t maintain while traveling. When I started scrambling for remote work, I was able to land my first content writing job online. That’s when I realized my journalism resume was perfectly transferable to content writing roles, as well as other types of writing roles. And when COVID-19 started and I was booted out of the budget hostel I was staying in, I was able to pay rent for several months in Tel Aviv, recently ranked more expensive to live in than Los Angeles.

You may be thinking duh, journalism is pretty similar to content writing. But I have to tell you, hindsight is 2020. I never thought I would do anything but write scripts for TV newscasts. 

So if this is an option you’d like to consider, you have to take a good hard look at your skills, and flip the lens. How can you utilize your skills differently, what other feature of your work can you highlight?

Find any remote work online in a new field

This option is ideal if you’re not particularly attached to your field of work, and you’d mostly like to just finance your travels. Why do I say it’s ideal? Because if you’re willing to take on a wide variety of roles, it’ll be much easier for you to piece together an income to travel as a digital nomad.

Here’s my secret: I don’t particularly love all of my content writing gigs . It’s not necessarily all work I feel passionate about. Some of it I enjoy. And at the end of the day, I have the freedom of working from anywhere in the world.

The more flexible you are, the more jobs you can potentially take on. My advice? Prioritize finding roles in your career or adjacent to it, and if you need to, supplement your work with other gigs or roles.

If you're looking for remote jobs hiring right now, check out this post.

Becoming a “digital nomad” is not a role someone hands to you. You have to make this path for yourself. And you're probably going to have to fight for it.

The great thing about finding new remote work is that you can choose to work freelance, part time, or full time. I currently work as a freelancer, which has fit in perfectly with the “nomad” parts of my digital nomad life.

And here’s my last point: once you land a remote work opportunity, you’re truly free to travel the world, without stressing about the potential future consequences of quitting your job, and while earning income on the road. If that's a dream of yours, I'm here to tell you it can be your reality.

Psst.... interested in becoming a digital nomad? Download my free digital nomad guide. I also have travel guides on India and Israel.