Inspiration: 3 Travelers that I aspire to be like

I have been doing some digging around on the net lately to see if others out there are doing what I aspire to do: travel perpetually. I found a few that are "living the dream" that I am working on every day. None of these blogs seperately do what I intend. My dream encompasses a mixture of all of them

The Blogs:

Overall the combination of these 3 blogs is what I want to do. Todd in the first link teaches English and does some volunteer work. The second is an interview with a couple who have enough income from investments to travel the world and live cheaply. The last guy is truly traveling and seeing the world without a specific income. These all sound great to me.

My intention is to combine the 3 to achieve what I want. I don't mind working just don't want to do it ALL of the time. I would also have some reserve savings and side income that will help support at least some of my travels. Finally I will do some traveling purely for pleasure. A month or two just simply enjoying a beach town sounds good.

The obvious questions is: How do I make this happen both logisitically and financially?

So far I have a basic plan that I believe will build upon itself to reach my ultimate goal of being a semi-nomad. I broke it up into major steps:
  1. Become debt free and build savings. This critical step is to reduce my expenses to minimum. Ideally I would have my house paid for but would entertain renting it out. Either way I have a place to come back too. I would also have a $10,000 reserve that I do not touch. If the plan failed somehow and I had to come back to full time work this would be my safety net.
  2. Transition from working to semi-retirement/traveling. The details here are fuzzy but I am considering teaching English for a couple of years or lining up some project-based work with defined beginning and end. Would travel between contracts (overseas) to transition. At this point I am financially secure enough to not have to work full time if I choose not too.
  3. Freedom: Between side income, my savings, and planned working stints I have the security I need where I can decide where I want to go and what I want to do. I have found places where I can "home base" and travel into and out of. I will discover these as I go. One place that works for this is Bangkok.
As of today this is my game plan. Adjusting my habits and keeping my eye on the prize is the most difficult part. Big goals do not materialize without some sacrifice. I am making progress but certainly not as quickly as I would like. Patience is one of the hardest things to learn.