Three paths to being a digital nomad
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.
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.
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.
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 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.