Choosing Homelessness

I met a neat guy a couple days ago. He was young, college aged, and full of energy and intelligence. He was a quick thinker and good conversationalist. I met him while I was couch surfing in Florida, staying with an awesome and independent woman and her homeschooled teenage boys. They had met this guy, Addison, while at an Unschooling conference in the Midwest.

Addison had been invited by a friend to the conference and he hitchhiked across a couple states to attend. He mentioned the journey as being “interesting,” which being from the Midwest, I was curious about the details of that hitch hiking experience.

Making friends while traveling.

Making friends while traveling.


Through talking I found out he had left school at age 16, and continued his education himself. He said he had been taking free online courses and mentioned a current textbook he was reading. Like me he was interested in history and he asked me about being a teacher, as he had considered becoming a history teacher.

I could see that during his travels, with a backpack and a guitar, he was experiencing the United States in a way that few people do. Using little to no money, he had hitchhiked and train hopped and met people from all over. Recently he had been sitting on a college campus in Birmingham, Alabama, when a policeman approached him. As Addison told us the story, the cop had disliked Addison’s refusal to show ID (which was legal) and in a show of authority arrested Addison with excessive force. Fortunately for Addison the unnecessary physical arrest was captured on camera and the university stood behind him as he became popular in the news. He’ll likely win a lawsuit, though the stress of the court date and legal battle was dampening his trip.

I liked meeting Addison because he is a traveler like me, refusing to run the rat race and instead choosing valuable memories and experiences. He’s smart, well dressed, and social, yet technically a “transient.” His transientness is what made the cop suspicious about his presence on campus in Birmingham.

While traveling I visited my best friend Melanie in New York, she asked me to help her feed the homeless in downtown Saratoga Springs. It’s a wealthy town known for horse racing, and she had seen the homeless people sitting on the street repeatedly and couldn’t bear to not do something about it. I helped her deliver chili and homemade bread in styrofoam containers, with her 4 children in tow. One man in particular, overweight and picky about what he eats, I found out later has money in a bank account and was kicked out of the shelter for not actually being “in need.” Melanie and I are both interested in the topic and causes and different types of homelessness. Addiction and mental illness are common, but each person has a different story and more or less support depending on their network. Since that night Melanie has continued to feed and support the homeless in Saratoga and began training at a local shelter.

Our eyes can play tricks on us when it comes to the homeless. I met a young male street musician in St. Augustine that played guitar and sang for cash, while his dad owned a private jet and was the CEO of a wealthy company. The boy was just finding himself and going back and forth between home, school, and trying to support himself. He most likely had a safe place to sleep, but you never know unless you ask. When I was a teacher I learned about the surprisingly large number of students that slept at friends houses, floating from one place to another. The topic is interesting to me, but most of all I am interested in the people that have a home but for whatever reason they have chosen to be on the move.

I’m very attuned to transients, backpackers, long distance hikers, or people on any kind of personal quest that blurs the line between normal and homeless. My current quest started with a 12 day kayak trip across the state of Missouri. Everything I needed to survive was in my kayak: food, tent, gear. I went multiple days without showering or washing the few clothing items I had. I sat around campfires and ate ramen noodles and beans from a can. This was not homelessness, it was a chosen adventure on the Missouri River. But it sure was an interesting way to start off my journey into full time traveling, as I often remember those moments of sleeping in the elements, noticing how bad I smelt, and dreaming of French fries and a hot shower. After that long kayak trip I drove across the country in my tiny car listening to Wild in the form of an audiobook. There’s a funny moment when Cheryl Strayed, the author, is walking off the Pacific Crest Trail, hitchhiking to a town to resupply on food and water, and a man stops his vehicle. He was a journalist writing stories on homeless people, and she kept having to yell at him, “I’m not homeless!” He gave her a homeless “gift kit” with snacks, a can of beer, and some hygiene items. Although Cheryl Strayed wasn’t homeless, she snuck off into the ditch and downed that beer and snacks in true hunger and thought about how she actually didn’t own a home. She had saved up money to go on this long distance hike and only had her backpack and survival gear. She certainly blurred the line.

Cheryl Strayed on the Pacific Crest Trail

Cheryl Strayed on the Pacific Crest Trail

It’s already been almost 2 years since I chose to leave the teaching profession, sell or give away all of my belongings, and travel full time. I do workaway jobs in the U.S. while I build an online business based around what I love: art, fitness, and travel. But here I sit in my car, typing this blog on my iPad. I’ve just left one house and will visit two friends as I travel to my next workaway location down in the Florida keys. Next to me in the passenger seat is my suitcase and my cooler full of food. I’m not homeless……though I don’t have a home.

Well, I have a home. Just not a house. I have family and friends and a huge network and I never have to worry about going hungry because I know they wouldn’t allow that to happen. I’d never have to sleep outside in the cold either. If worse ever came to worse, I know I could get help, and I know I could get out of it. I can pick up part time work at any time knowing that I am overqualified for most of the jobs that I would take. I may get frustrated trying to balance work and business building and traveling, but it is my choice. I can stop and be normal at any time. So could Addison. Well…….I think I could, but I’ve made it so far now I’m not sure I can ever be normal again. And I’m meeting more and more fascinating people as I go and having amazing experiences and stories to tell. I have a feeling any attempts at normalcy from now on would feel fake. I can dress the part and go to work every day and watch that money disappear into the abyss of the “cost of living” or I can simply walk away….and taste the adventure of a life that feels so much more alive.

Nearing the end of the Missouri River.

Nearing the end of the Missouri River.

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