First things first. Thank you for the title, "I Can Make A Mess Like Nobody's Business".
Since leaving the comforts of an established and regular living arrangement (AKA an apartment) in July, I've slept in a lot of different places. In Minnesota I never found myself sleeping outside. Homeless life is easy when you are as mega popular as I am. I found it hard to be able to sleep in my car then. Friends would ask me where I was sleeping, and when I said in my car or I don't know, they would say something like, "my couch". I have one friend and former co-worker who would give me her apartment keys and have me sleep on her couch while she was working an overnight shift.
So on September 11th when I left Minnesota and the comforts of friends i had to figure things out for myself. My friends reached much farther than I suspected and I found myself on a couch a few other places throughout my journeys. In Rapid City, Salt Lake City, and Seattle I found myself with familiar people and on a couch for at least a few of the nights.
In Rapid City most nights I spent curled up in the back seat of my car. I'd park in the Wal-Mart parking lot, move everything from the back seat to the front and put towels in the back windows of my car, and there I would slumber.
Salt Lake City (and the surrounding area) was pretty much the same deal. It was still warm out and so at Wal-Mart or a residential street I would find myself to end each day.
In Seattle I realized that I'd spent far too much money on gas from driving around those last two cities. I found a quiet Buddhist neighborhood and there my car stayed pretty much the whole time I was there. I would move it from place to place everyday, but it never moved more than a block from where it was the day before.
By this time, my knees were beginning to feel the affects of being curled up in a small space every night. So at the behest of my knees and an old friend wanting me to live the sort of homeless life he felt was the only way to be homeless, I went on search for a place to "camp" in Olympia, WA. I found one such place between a row of bushes and a Baptist church.
The thing with sleeping outside in a city is that it's not very safe and actually pretty illegal in most cities, so you have to hide. Let me explain something that most people don't think of about the safety issue. In Portland, I met a young man named Nick. Nick is from Vermont, and hasn't ever really had the best home life. His mom, kicked him out of the house when he was 16 years old, and for most of the last 4 years Nick has hitch hiked around the country. A few days before I met him, a friend and I started seeing a lot of homeless people with big open sores and just looking really beat up. When I met Nick, both of his eyes were black and his right hand was broken.
This is Nick's story. He woke up to three teenage boys beating him up and robbing him late at night in a park. He fought them off and was able to get back most of his things, but not without some pretty nasty injuries.
The moral of the story is that it's not usually the other homeless people that I have to hide from when it comes to sleeping outside, it's often kids who are probably intoxicated with too much time on their hands. So the trick is to sleep in darker parks where you're not likely to be found.
Year round homeless shelters are making more space for people trying to escape the cold and more and more churches are opening their doors as "Winter Shelters". On top of these extra shelters, when the cold gets dangerous, Emergency Shelters are opened. I stayed in one such shelter a few days before Thanksgiving. It was a Red Cross run shelter inside of a church in East Portland. The night I was there, they housed just over 150 people and maybe about 25 dogs and I think 2 cats.
On the way down the coast from Portland to San Francisco, I spent one night camped in my tent on the shore of the Pacific Ocean. This brought with it a few fears. One: I had to camp in a place where no one would see me, the last thing I wanted was to get woken up in the middle of the night and either kicked off the beach or arrested. Two: I had to be higher than the tide.
And so life goes on just has it has the past three months. In the winter, if the first shelter I go to is full, they will call around until they find a place for me to sleep safely. In the colder months there's always somewhere to go, to stay warm, dry and comfortable.