Three paths to being a digital nomad

Photo: Philip Brewer

I wanted to be a digital nomad before anybody--before the term existed; before the technology existed; before most people even imagined that it would someday be possible to earn a living without ever being in the same place as your coworkers, bosses, customers, or clients.  Other people may have become digital nomads before I did, but nobody wanted to be one before I did.  

Three obstacles define the three paths to being a digital nomad.  

First, there was the technological barrier--one that has been largely overcome by the earliest digital nomads.

The Road-Warriors

People whose regular job required constant travel--salesmen, executives, managers and technical folks with far-flung teams--were nomads before they were digital nomads.  It was on their behalf that the technology was gradually beaten into submission.   I knew a lot of these folks--people who paid top-dollar for a computer (just) small enough that it would fit into a suitcase and (barely) light enough to be carried by one person.  An excellent article in a recent Economist, quotes Paul Saffo as saying that "nomads" is the wrong term for those early strivers:

Since these machines, large and small, were portable, people assumed that they also made their owners mobile. Not so. The proper metaphor for somebody who carries portable but unwieldy and cumbersome infrastructure is that of an astronaut rather than a nomad.

Exactly so.

The technological barrier is down, now.  The equipment is small, cheap, and highly functional.  (Although there are still challenges even with modern high-tech gear.  For some nitty-gritty details on actually getting things done while on the road, see High-Tech and Homeless.)  I never wanted to be a road-warrior, though.  Having to show up every day at one specific workspace was bad enough--I most definitely didn't want to put myself in the position of having to show up at dozens of different specific workspaces.  It was one of the paths that has eventually led to a kind of digital nomad, but not the path for me.  

Long before the technology really supported the road-warrier, it became good enough (and cheap enough) that it was practical to create a fully functional workspace that wasn't at the office.  The technological barrier, although not yet down, had become low enough that it could be easily stepped over.  But close behind was a series of management and personal barriers.

The Telecommuters

People whose regular job can be done on a computer were digital before they were nomads.  For almost twenty years now, the technology has been good enough that pretty much any digital job could be done at home, or really, anywhere--as long as "anywhere" was one specific place where the equipment could be set up and a data connection established.

Bosses never liked telecommuting--if they couldn't walk over and see you working, they were pretty sure that you probably weren't.  And, since the sort of jobs that could be done entirely on a computer over a data link tended to also be the sort where managers--even managers with a good bit of technical savvy--had no idea how much work was actually involved in any particular task, there wasn't really any other way to tell if someone was working hard or hardly working.

The result of all that was that most managers would only let certain employees telecommute--the ones they trusted to work hard without supervision, and certain other key technical people who might leave the company if their whim to telecommute wasn't indulged.

Once the equipment got cheap--especially after it got cheap enough that employees could afford to buy their own--employers were quite prepared for employees to have workspaces at home.  But that was just so that the employees could work more, not so they could quit coming into the office.

Still, telecommuting has grown.  Lots of people do it now.  Especially since fuel got so expensive, there has been a surge in people working at home one or two days a week.  Obviously that saves time and fuel, while still giving the boss the chance to observe them working on the other days.  

With the technical barriers down, though, the mere telecommuter can now be a digital nomad.  The boss may imagine you sitting in a home office, working on desktop machine not much different from the one in your cubicle, but there's nothing to keep you from taking your laptop to the library or the coffee shop or the public park--anywhere you can get a network connection.  In fact, if there's no danger of being urgently called into the office, there's nothing to keep you from taking your laptop literally anywhere--even halfway around the world.

Telecommuting is a second path to being a digital nomad.  I did a little telecommuting, but it wasn't for me.  To thrive as a telecommuter you need to be both self-motivating and self-limiting.  Too little of the former, and you're not productive.  Too little of the latter and your home office turns into a home sweatshop.  (It's very easy to find yourself working from 6 AM until 10 PM, checking email at all hours, feeling pressure to be always-accessible since people can't just catch you in the hallway at the office.)  With just a little experience at it, I found that I suffered from both those deficiencies, so I avoided telecommuting after that.

The hard work of crossing the managerial barrier is largely done--telecommuting is a fact and most companies have policies allowing limited forms already.  You can't really look to others to cross the personal barriers for you--you have to do that yourself.  If you find your way past those, there's really only one remaining barrier--money--that keeps people off the ultimate path for the digital nomad.

The Freelancers

The technology is cheap and easy.  If you don't have a regular job, you don't need to get anyone's permission to telecommute.  As a freelancer, you can work wherever, whenever, and however you want.  The limiting factor is earning enough money to support yourself.

You can freelance at just about anything.  Software is big, as is writing (fiction, non-fiction, screenplays, poetry, blogs...), and the arts (graphic design, photography, music, sculpture, painting, drawing, architecture...).  Especially big are the specific tasks that came of age at the same time as the technology of the digital nomad--freelance web design, for example.  There are freelance researchers, freelance editors, freelance accountants, freelance technical support.  Of course, you're really only a digital nomad if a large fraction of your freelance work can be done digitally--there's not much call for digital massage therapy or digital hairstyling--but the range of things that can be done on-line keeps growing.

If you're of an entrepreneurial bent (or know someone who is), you can go the route of the "virtual corporation"--put together (or join) a small team of people who come together to create a new product, outsource anything that they don't have the expertise to do themselves, and once they're done, go their separate ways.  (This sort of thing is very scalable.  See Tim Ferriss's The 4-Hour Workweek for some examples of what amounts to one-person versions of this sort of business.  There's also some info in my review of the book from last year.)

You can make money at any of these things.  Some people can make a lot of money doing freelance work.  But for most people, freelance work is going to pay less than they can get working a regular job.  To make it pay even a large fraction as much will likely require working a whole second parallel job (marketing your freelance service) plus a third parallel job (managing the business--invoicing, collecting, accounting, etc).

This is why I talk so much about frugality.  Maybe you can earn a lot of money and maybe you can't--but anybody can get by on less money.  And, if you can get by on what you can earn freelancing as a digital nomad, you can be as free as anyone has been since hunter-gatherers took up agriculture.

It's what I've always wanted to do.

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Guest's picture

I love the conclusion - with a little frugality, you can live your dreams. (That's the conclusion I came to, anyway.)

Nice article.

Myscha Theriault's picture

I'm currently in cyber-nomad land myself. It brings its conveniences and struggles, but sure beats having to solve some of the issues we are now solving while showing up at an office every day.

Guest's picture

I loved your article! I became a freelancer and I also live the dream with much less money. After getting my MA degree and working full-time for just 2 years, I discovered that working at an office and doing the 9 to 5 thing wasn't for me. I slowly started getting clients and working during my spare time. In the beginning I was making enough extra cash to perhaps pay my Internet connection -- even so, it was a great feeling to know that with a little hard work I could enjoy more of my time the way I wanted to. It took me about five years to be able to live off my freelancing. Like you said, you have to learn to live with less money, and being frugal is the key to this. But working in my PJs if I want to, from my deck, or just being able to tell my client that I'm taking days off, instead of asking for that time, is priceless.

Philip Brewer's picture

There's nothing better than living the life you want.

By the way, the Economist article that I link to above is part of a whole special section on digital nomads--eight or nine articles, all worth reading.  Look in the side bar under "In this special report."

Guest's picture

I'm looking forward to be a freelancer too. Just like you, I found 9-6 schedule too restricting and limits my freedom. As of now, I have that sched while on the sideline doing freelance too. If ever my freelance work get more clients and hopefully if it even equals my working salary, ill go full-time.

I submit to the author's view that anybody can survive on less money. Maybe we need to shut ourselves to the world's materialistic point of view to free ourselves to have more money to buy more stuffs.

Fix My Personal Finance

Guest's picture

Many more people in the U.S. would likely follow this path if we had a health care system that guaranteed coverage at a reasonable price. My husband and I both freelanced as journalists at the national level for many years, and even embraced frugality happily. But the hit from health insurance was too great. One of us needed a job that provided benefits.

Guest's picture

Wow! So, Gina, you can live the life you want, but you want someone else to pay for the health care?

You probably want dental care, day care, housing assistance, perhaps a gasoline or transportation credit.

I live the life I want without public assistance.

Philip Brewer's picture

@ Gina:

I wrote a post on exactly that topic:

Philip Brewer's picture


It sounded to me like Gina wanted affordable health insurance.

I really don't see that as wanting "other people" to pay for your health care.  People don't usually talk about car insurance as wanting "other people" to pay for your car accidents or homeowners insurance as wanting "other people" to pay for damage to your house.

Guest's picture


I understand Gina wishes for affordable health care - hey, so do I. But - as my daughter's kindergarten teacher told her - 'you get what you get and don't make a fuss.

It is what it is. I have pretty good ideas how the system could be reformed and work better, but no one's listening to lil' ol' me.

I pay a heavy premium for health insurance for me and my wife. I'm self-employed and, trust me, writing that ck quarterly is a killer. But I'm not going without and I guess I have to deprive myself of some other things, things I'd rather have. But, that's life.

When people talk about affordable health care, most of the time that means 'subsidized' health care. Someone else will carry part of the burden. I'm burdened enough thank you.

People talk of the uninsured in this country, and I agree it's a problem. But... of the 40 or so million uninsured, 22 million voluntarily opt out. They can, but choose not to pay the premium. They include many of the 30 and under crowd, but others who are willing to risk it and use the money for other things. Last time I checked, it was still a semi-free country and you can do this.

Another chunk of the uninsured are the underpaid, illiterate, destined to remain slaves, illegal workers. Since they put the number of illegals at anywhere from 10 to 20 million this is no small effect.

Then there is always the hope, the change of socialism! Whoops, meant to say Obamacare!

Philip Brewer's picture

I think there it's useful to look at subsized care in two different categories.

First, there's subsidizing care for poor people.  This, we already do, we just do it badly--poor people show up in the emergency room and get urgent care, paid for by the hospital, which then over-charges its regular patients to try to make up the difference.

Second, there's subsidizing care for sick people.  This we also already do, if you think of insurance as the people who don't make claims as "subsidizing" the people who do.  (I'm not sure that's a useful way of looking at it, but insurance is what we're talking about.)

Whether we ought to subsidize care for poor and sick people isn't really an issue--we already do.  What the debate over affordable health insurance is about (as far as I'm concerned) is making health insurance follow the "insurance" model--provide coverage that protects people from bankruptcy simply because they become seriously ill.  Insurance like that is available, it just isn't available to anyone who's ever been seriously ill (unless they have a good job with a large employer).

That can be fixed pretty easily in several different ways.  And, I think, it can be done without driving up health care costs (through programs of the sort that you've advocated, such as high-deductable plans).  But I think the status quo is unacceptable.  My wife and I have affordable health insurance.  (It costs about two-thirds of what we pay for rent, or about the same as what we pay for groceries.)  But we're both healthy.  If we had ever been sick--or if we were to become sick in the future--we'd be screwed.  Our care would be paid for, but our insurance would become unaffordable or unavailable altogether.

Sometimes "take what you get and don't make a fuss" is a perfectly good strategy.  Other times, though, making a fuss is what's called for.  I think it's called for when people are being treated unfairly.  And, when people are being financially ruined simply because they get sick, I think that's unfair.

Guest's picture

My next door neighbor is a freelance fruit and vegetable picker from Mexico. He has no health insurance and simply goes to the
ER for all his medical needs. They even fixed his teeth and delivered his girlfriends baby. He has never paid for any of this. Unfortunately the hospital is closing down because it went bankrupt. No problem, he has just moved into another town and the hospital is only a few blocks away. Freelancing is the way to go.

Guest's picture

Great post and a lot for nomads to think about. As you've probably learned over the years, while everyone thinks romantically of the idea of being a digital nomad, sometimes its just a pain in the butt.

Cesar Torres just posted a story on some of the challenges of working remotely and the growing trend of coworking, working alone...together. Cesar is co-founder of Austin-based Conjunctured. Take a look at it if you get a chance.

Bruce Eric

Philip Brewer's picture

Yes, that's a great blog; I've been following it since it started.

Guest's picture

These are all good approaches, and I have done them all at one time or another. I would add another catch-all category of webpreneur, or something like that related to actually owning website properties that create income.

This can be selling your own products or services, affiliate products, or using advertising schemes to monetize the sites.

The idea once again is to be location independent using technology to build one or multiple virtual businesses.

Guest's picture

Great post! Great blog!

I'd like to suggest yet another path to become a digital nomad, and that’s to find a business that 1) already has products, 2) an online presence, and 3)a proven business model. These kinds of businesses are out there. And I’m not talking about the penny-ante multi-level stuff. Real businesses. My husband and I found one and just plug and play anywhere in the world. The key is simply doing your due diligence to determine if the business is right for you.

My husband and I are devoted LUXURY digital nomads. Being frugal was simply something that we weren’t interested in. We are currently on an open-ended world life tour and are focused on living our lives NOW, not later.

Thanks for your inspiration!

Don and Karla