Freelancing is a means of making an income without resorting to full scale wage slavery. Yes, a freelancer still has to work... and oftentimes this work is assigned by a client. Despite these drawbacks, there are still many benefits to working for yourself. The first and most obvious is flexibility. As a freelancer, you choose when you work, where you work, for whom you work, how you work, and under what conditions you work. As a freelancer, you are on more equal footing with those paying you. A typical wage slave is nothing but an obedient grunt: the boss says "kiss my ass" and the wage slave replies "sir, yes sir". But the freelancer is a hired gun. You choose which jobs you take and if the client says "kiss my ass" you can kick it instead.
There are lots of possibilities for freelancing... in almost any field: writing, teaching, consulting, yard work, computer programming, graphic design, massage, etc.... There are freelance opportunities for every education, every experience, and every temperment.
For example, I now make a living as both a freelance writer and a freelance English teacher. Since I'm an international nomad, I chose activities that I could do from anywhere in the world. As a writer, all I need is a laptop or internet access and I'm good to go. I can write and submit articles from anywhere in the world. One month I'm in Bangkok, the next month I'm in Chang Mai,.... then I head down to Malaysia to visit a friend... then off to India for a pilgrimage vacation-- all the while I can continue writing, submitting articles, and receiving an income. It's a fantastic way to be a hobopoet (for those who are not independently wealthy- which I am not).
Freelance English teaching requires a little more stability, but not much. English as a foreign language is in huge demand in almost every country in the world. This includes the United States, by the way, where there is a huge immigrant population that wants to learn English. Freelance teaching is a readily available source of income wherever I go in the world. I know I'll never starve because I can always find students. Typically I choose to teach private lessons to small groups, as this is much more lucrative than teaching one-on-one. Also, I've found that teaching only one student is difficult and boring-- the possibilities for interaction and communication are much more interesting with a small group of four or five than with just one person. Finally, by teaching small groups, I am able to charge students less per hour but still make a great hourly income myself. The freelance teaching option is a great option for neo-nomads who want to have an extended stay somewhere (a year or more). It is superior to working a full time job because you can create your own (generous) vacation and holiday schedule and thus have plenty of time for wandering and exploring the country.
For those with technical skills--- such as business experience or computer skills.... the possibilities are even more exciting and more lucrative. The first possibility is to follow the English teaching angle... but specialize in "English for Special Purposes". In other words, be a freelance teacher of Business English or Computer Science English. If your skills/experience are especially good, you could set yourself up as a freelance consultant. Approach small businesses and offer your services. I'm no businessman, so I recommend reading some books on establishing a consulting business, designing a business presentation, etc....
A very simple and low tech approach, if you have artistic abilities, is to sell your artwork. For example, a Thai friend of mine makes jewelry and sells it to tourists. He goes to Khao San Road every night, lays out a blanket, spreads out his jewelry, and does very well. In fact, he's expanded his freelancing into a small business-- now employs four workers and also sells wholesale to larger jewelry stores in Bangkok. When I was teaching in Korea, I met a couple that used to live in a sailboat in the Caribbean. They made jewelry and supported themselves by sailing from port to port, selling their stuff to tourists on the islands.
In fact, you don't even have to make your own stuff. Many travellers go to India and Thailand, buy large quantities of jewelry and artwork, and then support themselves in Seoul or Tokyo by selling it (at considerably inflated prices).
Finally, there is the tried and true art of busking. I met a "homeless" guy in Athens, Georgia who supported himself completely by playing his fiddle on street corners. In fact, he made enough money to buy a plane ticket to Sweden every year-- where he also busked for a living. The Fiddler is a troubadour in the very ancient sense of the word... a wandering traveller who makes his living through street-side musical performances. Such folks can be found in almost every city in the world.
So whether you are a potential "young homeless professional", a wandering teacher, a dharma bum writer, a cyberhobo, an artist, or a troubadour...... freelancing is an excellent way to live a neo-nomadic life (without starving or begging).