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How to be homeless
It made me 
"I neither anticipated nor regretted being homeless, and it taught me some lessons."
How I did it: I've been homeless on 3 occasions, and none were planned. On one occasion, it was due to poor planning and being convinced to go along with someone else's plan to get a new start. On the second occasion, it was due to having too much to drink, getting into an altercation with another tennant, and then getting evicted. On the third occasion, it was due to scapegoating due to my Asperger's Syndrome and bigotry against my HBS syndrome.
The first time on the streets taught me some valuable lessons. I was able to be alone, face myself, and think about things I had never thought about before. The 2nd time was quite liberating. I had to put up with hateful and bigoted landlords who were also thieves. Yet it was fear and a sense of lack which kept me there, and being homeless forced me to consider other options and a new place to live. The 3rd time was not so good in that it damaged my reputation.
Lessons & tips: 1. Try not to be homeless in your home town or a place where you'd consider settling down. People may not let you live it down.
2. Unless you can get into a homeless shelter, the best strategy is probably to avoid the attention of both sides of the law. You do not want to attract overzealous or brutal cops, nor do you want to attract criminals.
3. Believe it or not, adult bookstores can be a resource. If it is really cold at night and you have no place to go, they may be used for getting warm.
4. Be careful with fire. You may need to heat food or build a fire to keep warm. Just do not asphyxiate yourself, draw the attention of the wrong people, nor let the fire spread.
5. Be careful if you must shoplift for food, unless of course you want to be arrested/rescued.
6. Never let anyone see vulnerability or weakness while homeless, and avoid trusting others. Criminals prey on weakness.
7. If you cannot find a shelter that will take you in, sleeping outside may be an option. Try to find a place out of the way or hidden. I slept between a building and a wall where I was not seen by the police nor by undesirable persons. I had about 6 blankets and slept on a couple and covered with the rest. When everything got wet, I found an unlocked shed to hide/sleep in and was very careful not to get caught.
8. Do things to entertain your mind. Just walking around and exploring the area can be fun - just be careful. There are free publications available that you can pick up and read. There is the public library and book stores which do not mind browsing. If you have money to spend on entertainment, you might want to invest in a pocket-sized game, playing cards, and/or a small musical instrument. There are places like the public library where you can use the Internet for free, and that can be helpful in improving your situation.
9. Collecting scrap metal such as aluminum cans and garbage is a source of income. So is asking others for money or finding it on the ground. You may be able to play an instrument or sing for tips, assuming you have such abilities. Day labor places can be resources, unless of course you are receiving disability income and don't want to lose benefits.
10. If you can choose the town where you are homeless, choose one where there are plenty of places which give away food.
Resources: What got me off the streets the first time was an organization called Traveler's Aid, a United Way Agency. WalMart was good for getting supplies such as poster board and markers for making pan-handling signs. Dollar Stores are good places for getting cheap food items. The Salvation Army, various homeless shelters (some run in part by the United Way), and various soup kitchens are good for helping you get food.
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