How to escape?

We've been thinking lately, thinking a lot about quitting our jobs, selling everything we have and going for the unknown. The unknown world of not having any money and living off the world. After months of thinking and discussing, my biggest thought still is, "HOW THE HELL DID THEY DO IT?!" Pardon my french, but seriously. I've seen the documentaries and read the books, but still sit here wondering 'how can it be done.' 

Then I realize that they probably had the same thought in their own head the entire timed they schemed up their plan to escape. But was it planned, or did they just wake up one morning, walk out their front door and leave it all behind them? 

If I ever did leave my lifelong paradigm of hardworking work weeks and 'luxury' items behind me, it would be the biggest life changing experience of all. Now if only, I could get myself to start the climb over that mountain of much needed life lessons.