Interesting thread. I come to this as someone who has given up a corporate job/sports car/expense account lifestyle to go live in a small island in the middle of nowhere as a dive instructor (thatch hut, occasional snake in my bathroom, etc). Not as radically different as living on a bicycle but a drastic enough change that I can offer some points to consider that may apply here.
For starters, if this is REALLY what you want to do, go for it.
However, a few things to keep in mind:
- Touring and traveling may be fun for a certain amount of time, but for a lot of people, there is a need to do something useful and be productive. Even when I took a year off work to travel, by the end of it, I was itching to go back to work - not to earn money but just to feel that I was doing something constructive
- What happens if you get burnt out with not having a home, medical insurance, friends, etc? Traveling is great but too much of it, as with anything, can stop being fun. I am perfectly happy going off by myself for extended periods of time (have spent weeks at a stretch in the Himalayas without seeing another person), but it is always comforting to come back to friends after a while. You may think that you can do without it... but you dont really know until you have tried it. So try to have an exit path which lets you come back to a more "routine" lifestyle if you so desire.
- Money. I have taken a 80% paycut to do what I like, so I am the last person to argue in favor of chasing money. But you need a certain level in order to enjoy what you are doing (whatever that level is). Be sure that you can find a way to ensure that level of money.
I would suggest that perhaps a year-long sabbatical from one's regular life to try this would be a good way to go. And yes, I do agree - if anyone decides to do this, please keep a journal on CGOAB or Facebook or somewhere, so we can read about this.
V.