Writing this from Sevilla, Spain, where my wife and I have been living for about 2 weeks.

We've just completed 2 years of a digital nomad lifestyle, having previously spent between 1 to 11 months each in Madrid, Buenos Aires, Tulum (Mexico), Portland (Oregon) and Edinburgh. Of course those are bases from which we've also visited Mallorca, Granada, Lisbon, Uruguay, Santiago (Chile), Mendoza, Mérida, Dublin and Paris. This is done while working on average 7-8 billable hours, 5-6 days a week, with some gaps in between for "touristy stuff."

All of the advice in the article about settling in to a new place rings true, particularly the internet connectivity situation. We've had difficulties in about half the places we've lived, but have also had the good fortune of incredibly considerate locals who have bent over backwards to assist.

Because we're both working, we decided to keep our house in Los Angeles and rent it out. We started with my friend acting as a property manager, but have since found that as long as we have a handyman, plumber and various other maintenance and repair people, the middleman only causes delays in communication. It's pretty amazing what can be done from the other side of the world.

We'll be in Europe until the end of January (as Americans, the Schengen agreement is a continual thorn in our plans), and haven't yet determined where we'll head next. Financially, the expensive part is hopping from place to place. If you can find somewhere whose tourist visas allow 6 months (UK, Mexico) or where you can pop across the border for a day and get it renewed (Argentina), you can cut down on a lot of expenses (and stress) by planting yourself for longer.

All that said, I highly recommend it. The opportunity to experience other cultures, learn a new language, and gain a different perspective on life is invaluable. Even for the process of winnowing your "stuff" down to what you're willing to carry with you while traveling for months on end.

It also has the side benefit of making you one of the more interesting people at any gathering you attend.

I tried this many moons ago and unless you have some sort of unique, valuable skill that new clients will put up with limited communications it will be really, really hard. I was able to gain clients in the city but after I left and the project finished I was left dry. Most of the nomads I've met already had a long standing, ongoing relation with their job (ie. the server admin that knows and ran the platform at one time, the webapp programmer that was in the office, built the stack, and now just updates it from time to time).

It was me working in some internet cafe somewhere in SE Asia versus the guy that can be down to their office for a face to face in 30 minutes. While there are successes on rentacoder and odesk these are the exception. Mostly you'll be competing against some guy with much lower overhead in a developing country.

After a while I realized that my objectives were orthogonal to the clients. I wanted to travel first and work second. They wanted the work done on demand and didn't care if you were 2 days away from your next port of call.

If you want to be a nomad, be a nomad first. That means taking whatever job you need to raise money. I've done app dev, translation, babysitting, bartending, ushering, and electronic repair. I've met ex-developers from the dotcom bubble who were now working as crew on a yacht.

I've just left the UK and am attempting it... so far so good although far more nervous breakdown moments than I'd anticipated.

Life on the road seems cheaper than life in London, but I don't get as much good work done because I'm not self-disciplined enough.

That'll change when I settle in one place for a month or more (right now I'm spending a few days each in various towns in Spain..)

Quit my job in December and been running my own business from the road since. Been to Dominican Republic, Jordan, did a 2 month road trip around the states and visited a few other places.

The great parts are flexibility, ability to travel, and low costs.

The much more difficult parts tend to be socially-focused rather than business-related.

Around 7 years ago, I went on a vacation to Japan and Korea and I had made more money after I came back from Adsense income. Decided I could do my job from anywhere and moved to Korea and been here since.