Wondering if it's frowned upon in buddhism to undertake homelessness without ordination. A focus toward meditation of course. With mind and body able to work for oneself.
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Homelessness is simply freedom from home-boundedness.
Homelessness is too negative a term. Those who wander free of homes do have their concerns, such as deciding in which beautiful place to sleep tonight, but this is minor compared to the distractions of 30-year mortgages, ever-growing utility bills, the complexities of adequate property insurance, too many neighbors, the hope of an adequate retirement many, many years from now...
One path is not better than the other, and haughty frowns of judgement may be thrown in either direction. One thing is certain: Do not choose your path based on who may or may not frown at you!
A time of homelessness (as the home-bound like to call it) has been an essential period in the lives of many great seekers, the Buddha, Lau Tzu and Jesus being only a few obvious examples. The key is to be homeless with awareness, but this is equally true for the home-bound.