You've got me there. I'd be inclined to make an exception for saints, if not bloggers (although I'm not aware if Francis ever broke into an unoccupied house). I also doubt retirement planning was much of an issue in the 12th century. Nor was there a well-founded expectation that the taxpayers would keep you from starving, so the "money-free" life would have involved much higher stakes than it does today.
The people we're talking about here, have much more of a safety net to back them up than the saints of old. They're not risking much more than going on the dole. Holding oneself out as an example to emulate to some of the very same people who will someday be supporting you is a nice bit of Chutzpah, but is it really all that admirable?