The pic above is where I lived this winter.  It is also what inspired me to start an outreach for homeless buddhists.  That water in the background is not normally there, but due to the heavy rains this winter, the forest floor flooded.  Fortunately, I pitched the tent, just before the rainy season, on high ground, so the water did not reach the tent and I stayed dry inside it.  I certainly did have peace and quiet inside the tent, ideal conditions for practice.
The downside however, was that I could not attend evening Teachings, and other group events, for even with a flashlight, it was too difficult to find one's way around in the forest once it was dark, so even the offer of a ride would not help for it would mean a dangerous trek thru a dark forest at night.
And most of the daytime hours for the homeless are spent in lines, for meals, showers, and other services, and so I was unable to attend the few noon group sittings in town, since that would mean missing essential services, hygiene, and meals.  It was from this experience of being homeless after release from prison, and this isolation from a sense of community (sangha), that inspired me to find a way to help others in similar conditions.  All Buddhist traditions I've encountered thus far stress the need for a Teacher, a Spiritual Guide, a Guru, yet homelessness makes it very, very difficult to even attend teachings, let alone find a Teacher.  Thus my decision find a solution this problem for the homeless, to do what HIs Holiness said "turn obstacles into opportunities for positive change."  
“Untilled soil, however fertile it may be, will bear thistles and thorns; and so it is with man's mind.”

 St. Teresa of Avila 

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It's difficult for me even to understand how it is to practice when homeless. Your wish to start a Dharma Outreach for realesed prisoners seems good one. I hope you'll find the energy, support and help to be able to do it.

_/\_

Pake

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