I'm writing this article from a tiny 'desk' in a guesthouse in Chiang Mai, northern Thailand. The sunday street market and the didgeridoo street performers were amazing. Friday, my girlfriend and me will go back to Hanoi, Vietnam, and stay there 3 months. Before all that, we were in Cambodia and on a 3 months meditation retreat in Phuket, Thailand.
Sounds great? It is!
Do you want to do the same?
You disagree, because you don't know how? Don't worry. Most people don't think they could ever do something like that.
(Neither could I imagine this a few years ago. Now, I'm working for a small specialized consulting company partly as assistant of the CEO, partly doing everything else that needs to be done).
The truth is, you can learn to be a so-called "Digital Nomad". Of course, there are many ways to travel the world really cheap (have a look at the book "Vagabonding" by Rolf Potts), but the easiest method is to do some kind of computer-related work, be it programming, webdesign or teaching a language over skype.
You can learn everything you need to know on websites like www.lynda.com, www.udemy.com (if you check out Udemy, have a look on following site where you can find a whole variety of courses temporarily discounted or for free: http://jan.dyrda.org/html/udemy_coupons.html).
Since I don't do webdesign or programming, I don't know how you can find clients online, but websites such as www.elance.com might be a start (and many others that you can find if you search google for "elance alternatives"). There are tons of sites where you can offer to teach your mother-language online. A friend of mine does that, earning between $15-20 per hour and living in Thailand. Just search for "teach language online", of look for a facebook group and ask which sites are credible.
If you just type in google: "how to be a digital nomad", you get over 4 million sites - for sure there are some great courses how to become specifically a Digital Nomad. (But as with everything on the internet, beware of scams.)
There are great people out there who have quit their corporate jobs to become Digital Nomads. Two of them are the dutch couple Steven and Diana, be sure to check out their amazing website: http://www.digitalnomadz.nl/
Many communities for online workers exist, where people can exchange expertise about their online businesses (like the invite-only http://www.tropicalmba.com/), or conferences that are organized in beautiful locations that are good for online workers, f.ex. Tribe Wanted Bali (http://tribewantedbali.strikingly.com/).
You can find fellows when looking for facebook groups with your city name followed by "digital nomads", or the same in meetup (www.meetup.com, a tool to find interest-groups about just everything, anywhere).
Here is a nice interview with rather prominent people in the field of Digital Nomadism:
Additionally to finding people in your town via facebook and meetup, the page http://www.startuptravels.com/ seems to offer a great list of digital workers worldwide, whereas https://nomadlist.com/ has an overview on living expenses, wifi connectivity, popularity etc. of all the nomads hubs.
Find below than cheap flights by looking specifically for "error-fares", which are created by mistakes in the booking systems of airlines. A german websites that lists many such insanely cheap flights is www.travel-cheaper.de. Or https://skiplagged.com/, which uses different tricks to get you cheaper flights than normally possible. They are so good, they got sued by United Airlines.
There is also Chris Guillebeau with his 'Travel Hacking Cartel'. The name sais much, check it out here: http://travelhacking.org/
You can get a very cheap landline phone number in any country you wish (usually around $2 / month). If someone calls that number, the calls will be secretly forwarded to your online voicemail, your online voip software (so that you can receive the call on your computer, with a headset connected), or to your local cell phone in whichever country you are. The costs are extremely cheap, and the caller doesn't notice anything, except maybe a not 100% optimum voice connection. A good service that I'm using is www.sonetel.com.
If you want to call people abroad, even cheaper than Sonetel one of the 60 voip providers from here: http://calltariff.com/. You can type in, to which country you wish to call, and Calltariff will show you which voip provider is the cheapest one. Some of them (f.ex. my favorite www.powervoip.com) allow you even to call from your internet browser. To a cell phone in the Netherlands f.ex. for less than $0,01. And all of the listed providers work together with an app for your smartphone, called 'Mobilevoip' (http://www.mobilevoip.com/). You can initiate calls from your phone via local mobile internet, via callback to your local phone number, or via call through if you have a flatrate.
For Thailand, the only way to stay longer than 2, 3 months in the country is by doing a year long language course of around 4h time investment per month. Many people are doing it, and you are officially not allowed to work.
For Vietnam, you can get a 3 months tourist visa, or a 3 months business visa, which can be extended relatively easily (not sure about his, though).
Other places might offer easier ways of staying long term. Philippines and Indonesia might be such places, I'm not sure.
If you plan to do some volunteering, you can visit www.workaway.info and www.idealist.org. The trade is supporting a local project, hostel etc., for 4-5h a day in exchange for housing and accommodation. It's a great way of experiencing a country without getting poor, and at the same time doing something good.
You see, there are many possibilities, many great resources, many beautiful stories, and who knows, maybe many new experiences that you are going to make….
Update: some links on making money online:
. very helpful blogpost with a nice overview on several ways to earn money online
. list of english teaching companies
. blogpost about teaching english online
. earn money as a micro-consultant on different topics
. do virtual tasks for others
. this one is not for earning money, but offering your services and exchanging your time for other services: TimeRepublik