The Rise of the Digital Nomad, Part 2

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The concept of digital nomads—a career path that is completely untethered by traditional office culture—may sound too good to be true. But it can be doable and highly rewarding, if you know what to look for. We spoke to digital nomads Sivan Lev-Eyal, a UI designer based in Israel, and Skyler Seamans, an iOs developer, to get a better idea of the expectations versus the reality of a digital nomadic career. In this article, we'll look at what you need to consider before deciding if this lifestyle is right for you. If you missed Part 1, click here to learn about the perks and what it’s like starting out in this career path.

What to Consider
If a digital nomadic career sounds too good to be true, there are some important practical elements to factor in. Lev-Eyal notes that the lifestyle is not always easy and not for everyone. Finding an employer who embraces and supports remote work can be difficult because the concept is still new to many industries.

“I keep applying to many roles, keep improving my resume and cover letter, but sometimes I get a reply saying the company is only interested in [remote work] candidates located in the USA, even though I don’t apply for roles that specify this restriction.” For job hunters, remote can mean within a certain geographical area still, and it can be frustrating and time-consuming to parcel this information while job hunting.

But remote work is becoming more feasible. Upwork’s future workforce report notes, “Nearly two-thirds (63 percent) of companies today have remote workers, yet a majority lack remote work policies.” With any workplace culture shift, hesitant companies are waiting to see how this new trend works out before investing in it themselves. While this can be frustrating for a hustling remote worker, support resources, like job boards such as, and global community forums, such Pangian, can help digital nomads navigate this non-traditional career path. Online communities and co-working spaces also connect fellow remote workers from across the world and industries, effectively creating a lifeline for digital nomads.

Beyond the Job Hunt
Once a quality, steady remote job is found, there are other important factors to consider, such as how to find healthcare and reliable payment services. These elements are usually handled by HR in a typical company structure, or individually for a freelancer or independent contractor. Digital nomads can fall anywhere in between, depending on the company, which can lead to harsh lessons to learn.

“When I first started, I couldn’t find a good way to get cash in other countries without first having to fork over money just to receive it or lose money in exchanging currencies,” says Katherine Langley, an educational specialist for an e-learning company, who started her digital nomad career teaching English to students in South Korea, while living in Costa Rica. Issues with paying taxes abroad or through other countries and working on a visa or not (and all the paperwork that goes with that) are other hurdles to cross for the newly-minted digital nomad.

Seamans noted the other general downsides of a 100% remote career: “Less social time with colleagues. It’s harder to show work in progress; I can’t just walk to a colleague’s desk with a build on my phone. Tone can be lost when relying heavily on chat; it’s important to get on a video conference for some conversations. And since I travel full time, finding reliable and fast internet can be difficult and expensive.”

All of those being true, the lure of autonomy and rewards of freedom are more enticing. Seamans says, “In terms of other benefits, my current job offers better benefits than my traditional job did previously. [Working] remotely full time is a huge perk to me. I would even take a pay cut to work 100% remote.” 

Making It Work
Contrary to what the term implies, a digital nomad must be rooted in their work ethic and stable in their professional performance so that they can be unrestricted by location. Impeccable organization, self-discipline and professional responsiveness are imperative traits for a successful digital nomad.

“I keep a set schedule and I typically work 9-5 in the local time zone that I’m in. The company I work for, TeamSnap, is a very remote-friendly workplace, so we’re all on an equal communication footing,” says Seamans.

Lev-Eyal adds, “I guess you have to have a free spirit [to work this way] but at the same time, you have to be professional, meet deadlines, be efficient, communicative and give perfect service to your clients.” This applies to regular cubicle life, the view just happens to be better for a digital nomad.

Complete Freedom
Clearly, for Seamans, Langley and Lev-Eyal, the pros of an autonomous work-life outweigh the cons. “I’ve been able to live in Costa Rica and Korea, and collectively I’ve spent [more than] a year in both countries while traveling to Cambodia, Japan and Panama,” says Langley. “The best experience has been to live in other countries, not just visit, and get a true understanding of what life is like. You never feel like you are stuck in one town. You can leave whenever you want.”

Seamans adds, “I’ve spent the last three years traveling North America, from Alaska down to the tip of Baja. The experiences have changed me and the memories will last a lifetime. Many people save and wait for retirement to see the world. I’ve been fortunate enough to explore while I’m young and maintain a career that provides financial stability at the same time.” For those with wanderlust, tech skills, and a sense of adventure, what could be better?