Travel While Working Remotely As a Digital Nomad

By Jared Shein

Christa wasn’t totally happy. Despite having the type of job she wanted in the city of her dreams, things were just not clicking.

Living in New York City and working in Public Relations was exactly what she thought she wanted, but after a few years of commuting between her small apartment and dark office building, she realized that her dreams were much bigger.

Christa wanted to see the world, and the ten vacation days she had per year at her job were not going to cut it. She decided to take matters into her own hands and booked a one-way flight to Thailand.

Having very little in savings, Christa’s plan to make her dreams of world travel a reality was to make money by teaching English abroad.

However, when she completed her TEFL (teaching English as a foreign language) course in October, she found that most schools were not able to hire her right away. She’d either have to wait until the next semester or look for a different kind of job.

She broadened her search, did her best to network in an unfamiliar country, and eventually found a job. She’d be working in the marketing department for a new English-language startup website, based in Bangkok. While Christa never found out if she’d love being an English teacher, she did learn to love her new office job– much that she ended up staying in Thailand for two years.

Life as a Digital Nomad

While the beginning of Christa’s story does involve a stationary office job, it was that first leap she took by moving abroad that set her up for her life as a digital nomad. She said that, had she not lived in Thailand, she wouldn’t have met so many people who inspired her to think about life and career from a different perspective. In fact, she may not have even learned what a digital nomad was!

But after two years abroad, working remotely was an obvious next step. For the last four years, she worked remotely for a US-based tech startup and has been traveling the world while maintaining her career in digital marketing.

Digital nomads are people with remote jobs who take advantage of their flexibility and travel the world while working. This lifestyle has become quite popular of late as it is getting easier and easier to work exclusively online and to explore and work in new countries.

While digital nomadism has grown in popularity of late, many people are still looking to ditch the daily grind and make money on the road. Forbes weighs in on the trend noting that, “In the recent MBO Partners State of Independence Research Brief, 4.8 million Americans described themselves as digital nomads.

Among traditional U.S. workers, 27% said they “might” become digital nomads in the next 2-3 years, and 11% said they planned to.”

But action is much harder than speech. There are many obstacles that stand in the way of becoming a full-time digital nomad.

Remote jobs are competitive and not available for all job types. It’s also difficult to plan logistically for life on the road. The social world is also very different on the road, and navigating the space can be difficult for some. It is doable though.

Here are some tips on how to join those 4.8 million digital nomads.

Find a Remote Job

The most important step to becoming a digital nomad is finding some sort of remote working arrangement. This can entail trying to negotiate a temporary or permanent arrangement with your current boss, or getting a new job entirely.

There are many great resources for remote job hunting, the best being remote job boards. Many of the top recruiting websites like indeed and ZipRecruiter have remote filters (or you can just search remote jobs in the search bar), and there are also plenty of websites entirely dedicated to remote jobs. Sites like hubstaff talent, pangian, remote.com, and weworkremotely are great for browsing and applying for remote jobs.

Teaching English abroad is also a very popular way to get your travel dreams started, and it is becoming an ever-popular occupation, especially for young people. Organizations like Language corps, Teachaway, and Go overseas are but a few good options.

Join the Digital Nomad Community

One of the scariest parts of going on the road is the social aspect. It’s tough to plan on spending a lot of time in a new place where you know no one.

A great way to get going socially while living abroad, or planning to is to join a digital nomad community. Again, there are 4.8 million other digital nomads, all of who also need friends, and these online communities are a great way to find them.

Websites like nomadlist, digital nomad community, and meetup.com can be great for finding other like-minded people in your area. There are also websites like outsite, and roam that set up co-working and co-living spaces for digital nomads, so you can meet people at home and at work.

Digital nomad conferences are also a great way to get into the community and to gather tips and information about entrepreneurship and remote work.

These conferences take place all over the world, from Nomad City in Canaria, Spain, to the location shifting Nomad Summit (their 2020 conference is in Chiang Mai, Thailand). More conference options can be found here.

You can also direct message Christa on Instagram for some more recommendations.

Keep Your Dream A Secret

“Never ever mention the fact that you want to travel as a motivation for getting a remote job,” advises Christa, “If you are applying for a remote job you should not treat it any differently then applying for any job. What you do outside of work isn’t your employer’s business.”

Do Research

I think this is the most important piece of advice, as everything in this article was found by doing lots and lots of online research. There is plenty of advice and plenty more good ideas for digital nomads, and prospective digital nomads alike on the good old world wide web. So hunker down, and spend some time with that trusty google search bar.

Remote Year

All of this research and planning can be quite difficult and time-consuming though, and although the planning and preparation for a digital nomad life is an exciting part of the journey for some people, others may not feel they have the time, energy or skills set to plan and prepare well enough, or might just want a little more of a push to get going.

There are plenty of options for people who feel this way, one of which is remoteyear.com. Remote Year can be the nudge you need to get going on a digital nomad lifestyle.

The company takes care of all of the remote work logistics like housing, flights, group activities, workspaces and a social network all for a little over the cost of rent.

Remote Year also has many different trip options from a 12 month around the world track, a 6 month Europe, Africa, and Latin America program, and 4-month programs in the Asia Pacific region, Latin America, and Europe and Africa.

“I remember looking at it and thinking ‘I could do this for much cheaper on my own,'” says Sean Stone, remote year alum and CEO and founder of Stone’s Goods. “However, once I actually signed up and started living the RY life I realized that there was no way I could have done even half of what I do on RY on my own. The sheer logistics that they sort out for you is unbelievable. You land in a new city every month and within 3 hours you’re fully functional.”

Don’t Give Up!

Despite your combination of enthusiasm, and knowledge (partially garnered from these tips) finding and adjusting to a remote life can still be difficult. Whether we like it or not, rejection is a huge part of any job search, and after getting a remote job, adjusting to a new country can be hard.

Despite this, Christa assures that you should keep at it, “There are so many opportunities out there, you just really have to look for them,” says Christa, “Ultimately, I think you will find one if you look.”

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