All Your Digital Nomad Questions Answered

So, what is this whole digital nomad business? What is a digital nomad? A modern gypsy? A backpacker with a laptop? Here are all your questions, answered.

Published on
June 27, 2018

It’s been 10 years since Tim Ferriss published his best-selling book, The 4-Hour Workweek: Escape 9-5, Live Anywhere. And though it’s been pointed out that Tsugio Makimoto first predicted this revolution in his 1997 book Digital Nomad, it’s only in recent years that we’ve seen an uptick, a “hockey stick growth” in this trend.

It looks like the shift happened in 2013/4, coinciding with when Basecamp published Remote: Office Not Required. It is interesting to note how this rise in digital nomadism occurred despite pushback from companies like Yahoo and IBM, who dismantled their remote work program in February 2013 and May 2017 respectively.

So, what is this whole digital nomad business? What is a digital nomad? A modern gypsy? A backpacker with a laptop? Here are all your questions, answered.



What is a digital nomad?

Tim Ferriss defines this as “individuals that leverage technology in order to work remotely and live an independent and nomadic lifestyle”. Note: “working remotely” also refers to telecommuting and working from home, which you may already be doing!

Who are they?

From a 2015/16 survey of 606 digital nomads:

  • 60% were male, and 40% female*
  • 32% were between 31-36 years old and 30% between 26-30.
  • 54% were in a relationship

*Nomad List’s sample of 10,000 nomads supports this: almost 60/40, up from 70/30.

How do they make money?

“Digital nomad” is not a profession, it’s a way of life. Household names like Accenture, eBay, S. C. Johnson & Son fully embrace remote working, and in so doing employ remote workers across their Marketing, Sales, Finance, Accounting, R&D, Engineering, Operations, Customer Service, and IT teams. In other words, you can make money as a digital nomad by being a marketer, salesperson, accountant, developer, and most professions under the sun.

Though instead of being a remote employee, you can choose to be self-employed, to consult, to freelance, to own a location-independent business, and there are also a variety of options for this. Some examples are teaching English online, creating and selling information products, online courses in your area of expertise, opening an eCommerce store, etc.



How much money do they make? Does digital nomadism make financial sense?

If you work remotely for a company, you’d typically make the same amount of money if you choose to work from home, or to work while traveling. Some companies like Buffer have a salary multiplier that factors in your cost of living, so you’d make more say if you live in New York than if you live in Cape Town. You can see Bufferoos’ salaries across functions here.

As well, to hire a remote worker does not mean to outsource. “Outsourcing” often has negative connotations - cue Silicon Valley Indian click farm clip - and as the old adage goes, you get what you pay for.

At Outsite’s recent Nomad Stories event, Pieter Levels of Nomad List described 3 types of nomads:

  1. Low-cost nomads who make $500/month from eBooks, blogging
  2. Freelancers who make $2,000/month working remotely for a company as a designer or developer
  3. “Freedom Nomads” who make $150,000-$200,000 per annum at big tech companies and demand to work remotely

Most digital nomads sit on this spectrum, and fall somewhere in or between one of the 3 groups. Places like Bali and Chiang Mai are hotspots for digital nomads in the first category likely due to the low cost of living (and high standard of living) it affords. I’d also add that besides high tech execs, there’s also a significant number of entrepreneurs that fall under category 3. Notably, Pat Flynn, and many of the guests on his podcast Smart Passive Income.


Becoming a Digital Nomad

How do I get started?

One strategy, as per Tim Ferriss’ The 4-Hour Workweek, is to negotiate a remote work arrangement with your current employer. He guides you on how to do so in his book, else another strategy is to moonlight. Start building your source of online income on the side, while keeping your day job. This can be consulting, freelancing, building a startup or ecommerce site. You might prefer to spend your “moon hours” applying for remote jobs, however it might be wise to not start nomading right away. Jason Fried tells of a Basecamp employee who was new to the company, and new to remote work. On top of that s/he took her work on the road to become a digital nomad. Long story short: it didn’t work out. First get used to working remotely - whether from home, coworking spaces, cafes - from the city you live in. Then, you can explore digital nomadism. Pieter Levels urges wannabe nomads to give it a fair shot. “Don’t just try it out for 2 weeks and say it’s not for you”, sublet your apartment for 2-3 months, then decide if you want to keep doing it full-time, part-time, or whenever you want. It doesn’t have to be all or nothing.

Directory of Remote Job Boards

EuropeRemotely is a remote job board for developers based in Europe.

Jobscribe sends a daily email with remote job openings at trending tech startups. They are tailored to designers, programmers, marketers, and writers.

Jobspresso is “the easiest way to find high quality remote careers in tech, marketing, customer support and more”. Their jobs 100% handpicked, manually reviewed and curated.

Outsourcely helps “helping talented individuals from around the world find reliable long-term remote work”. offers a hand curated list to “showcase the best remote job opportunities in the most recruited job categories”. They are aiming to be the premier remote work resource online, and are a sister site of FlexJobs. claims to be “an aggregation of the most recent remote jobs from the most popular sites, as well as our own listings, with the biggest list of +500 companies working remotely”. However there aren’t many listings and it doesn’t seem to be updated often.

Remote OK is “the largest collection of 25,000+ Remote Jobs for Digital Nomads”, of mostly engineer, developer, and designer roles. They also have an interesting page with live data on remote work statistics.

Remotive Jobs is a manually curated remote job board that was voted #1 "Product" in Tech on Product Hunt. SkipTheDrive provides pre-filtered job listings that allow for work-from-home opportunities.

Virtual Vocations provides “credible telecommuting and work from home jobs”.

We Work Remotely is “the best place to find and list jobs that aren’t restricted by commutes or a particular geographic area”. They urge visitors to hire remote in order to find “the most qualified people in the most unexpected places”. (Basecamp launched We Work Remotely in 2013 and sold it in 2017) is a job board focusing on digital and tech remote jobs

Working Nomads curates “the best digital jobs for those looking to start their telecommuting career”

Directory of Remote Company Directories - 121 leading remote companies and virtual teams

Remote Jobs repository on GitHub - crowdsourced list of semi to fully remote-friendly companies in or around tech

Remote OK - top 100 remote companies hiring in the last 90 days - 500+ startups who welcome and celebrate remote work, most of those are actively hiring.

SkipTheDrive - their 32 favourite remote companies

Virtual Vocations - 6,428 researched telecommute-friendly companies - 1,425 companies that hire remotely


Where do they live?

Digital nomads, whether full or part-time, live out of some form of apartment rental most of the time.

  • Many Airbnb listings apply automatic discounts for stays for 1 week or more. If I’m staying for a month I like to message the hosts for an even larger discount. American couple Kaitlyn Reed and Taylor Knight have been living out of Airbnbs for 5 years. Similar sites include HomeAway and VRBO.
  • Coliving spaces can increasingly be found in most cities. Outsite has coworking/coliving spots across California, as well as Hawaii, New York, Costa Rica, and Puerto Rico.
  • Home exchanges or house sitting arrangements are also great options. Sites like Workaway and HelpX even let you work in-exchange for accommodation.

If you’re a nomad seeking some social interaction, or want to test-drive this digital nomad thing, retreats can be a good option. Ex-Hacker Paradise Trip Facilitator Iskender Piyale-Sheard writes, “you’ve probably heard murmurs or gotten ads on Facebook about how to travel around the world for a year with a group of like-minded people. Today, these types of retreats are a dime a dozen. Everyone and their uncle has started some sort of travel+work, yoga+coworking, surfing+coworking retreat, and they can vary significantly in length, quality and price. Here’s a whole list of ones you can check out.

One’s living situation is the key difference between a remote worker and a digital nomad. A remote worker has freedom of location, but chooses to work from home, or at least their home city. They are free to travel and take trips. A digital nomad lives “on the road’ all, or some of the time, bouncing from place to place.

Where do they work?

A Google Image search of “digital nomad’ returns stock photographs of people working from laptops, by the beach. That’s the image of a “digital nomad” that many of us have, however ask any nomad and they’ll be quick to tell you that that simply isn’t practical - the glare, the sand, the lack of sockets. I tried it once - never again.

Airbnbs or hotels, as well as coffee shops, co-working spaces, and public libraries tend to be the go-to, and there’s a great mobile app that facilitates this. Work Hard Anywhere displays the best places to work remotely around the world. They have 7,000+ locations listed by freelancers, entrepreneurs, and remote workers.

Nitty Gritty

What visas are they on?

Most digital nomads, not to mention yoga teachers, retired expats, simply use tourist visas. Say if they are given 30 days, they can likely extend it for another 30, and beyond that, if they want to stay longer, many make “visa runs” to neighbouring countries. That is to exit the country, and be given another 30 days when you re-enter. Needless to say this does not always work. For example, the US keeps track of (and limits) the total number of days you are in their country per year. For Canadians, that is ~6 months. Nomadic Matt has a great post on how to (legally) stay in Europe for more than 90 days. The easiest way, if you’re under 30/35 years of age and a citizen of one of the few particular countries, is to get a working holiday visa. Alternatively, there’s long-term-stay visas, student visas, self-employment visas, or ahem, marriage.

How about travel insurance?

With the rise of digital nomadism comes the rise of services catered to digital nomads. For insurance, there’s World Nomads. The caveat with them and most/all private insurance is that you have to maintain your home, governmental insurance. Thing is you technically cannot do that if you do not live there for most of the year. As well, insurance for perpetual travellers is very expensive. Some opt for no insurance, as health care in Asia and quite a number of countries tend to be very affordable out of pocket.

What about taxes?

That’s a tricky question. According to Pieter Levels, what everybody is doing is illegal and no one’s talking about it. However he himself has a Dutch company where he pays corporate and then individual tax. An Australian Digital Nomad, Chris the Freelancer continues to pay tax as if he were living in Australia. Depending on where you are at, it might make sense to establish a company in a low-tax country.

Are you considering becoming a digital nomad? We are working on Nomad Stash, a curated directory of resources and tools to help you on your journey. Sign up here to be notified when it launches.

If you have a question about digital nomadism that we missed, tweet @nicolejfu

Words: Nicole Fu // Digital Nomad Extraordinaire

Photographs: Outsite

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