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The Bicycle Years in Portland Part 1



Losing my driver’s license was a blessing in disguise.

The big city life awaited me in Portland Oregon after I lost my driver’s license and decided living in a larger city may help my prospects.

The year was around 2005 in the early spring and I was in my late 20s.

Getting to the City

At first, I wanted to bring my gas-powered scooter on the Greyhound bus, but they didn’t allow it in the luggage compartment. Visions of flying around Portland with a gas scooter that was louder than a lawnmower were probably a bit naive anyway, especially since I would be homeless.

Having only around $250 to my name, rock-bottom credit, no driver’s license, no bank account, and not knowing anyone in Portland, I set my sights on the strange “big city” to get out of Eugene and make a new start.

Maybe it was the Cannabis clouding my judgment, as it was likely the culprit for me being in the tight spot I found myself in anyways, but it was my lot, my mind, and my life to navigate regardless.

After getting a refund for my Greyhound bus pass, I brainstormed selling my precious scooter and instead taking my Huffy mountain bike. I asked a friend to give me a ride after I sold the scooter and soon enough I found myself dropped off in Portland.

Finding a Storage Unit and Settling In

Having already experienced homelessness before, yet in a car, I knew the value of having a storage unit, so I spent some of my small supply of cash on a storage unit in the middle of Portland on the east side of the Willamette River.

I soon realized how strange of a place Portland was when I met a man who had small horns sticking out of his head; he was a nice man who worked at the storage center. Later, I realized he was a satanist fairly high in the command of a satanic organization.

Being dropped off, I said goodbye to my friend who gave me a few bucks for the journey and thus the bicycle years began.

The Huffy mountain bike I had was not a nice version; in fact, it would get flat tires almost every other day. This turned out to be very challenging, as I would find myself pushing the bike more than riding it and always trying to find a place to fix the flat.

One day, I went all the way down to the river to try and see the bubbles from the holes in the rubber tube. Being homeless without friends, family, a job, or a vehicle is tough — it is these little things that become the hardest challenges when homeless.

Going to the bathroom was always a challenge as well, trying to find a place to go would sometimes take hours. I remember waking up one day and finding a woman peeing about 10 feet from my head on the other side of a fence — she didn’t see me at first.

Sometimes I would go to a nice spot hidden from the hustle and bustle, yet in the middle of the city, only to find a large pile of crap there. That was something I wasn’t willing to do, I was determined to stay civilized.

Killingsworth St. Neighborhood

The beginning of my bicycle years began with riding my bike through the black neighborhood unknowingly right after I was dropped off and got my storage unit.

Before I knew it, I was cruising along the sidewalk across from a convenience store with a large group of young adult black men hanging outside of it. Here I was a scrawny white guy with my backpack on scrolling by like I was completely lost, which I was.

One black man (not affiliated with the crowd) came up to me and asked me for a dollar or two. Being gullible and helpful, I decided to give him two dollars. Somehow, through some sort of hustle lingo to get change, I gave him five dollars. He didn’t give me the change back, so I found myself arguing with this guy over three bucks.

This guy was a heroin addict, he told me all about his addiction and that he had to have it; I was lucky to find such a nice heroin addict because I was really out of place and about as green as you could get in the big city.

After trying to make him feel guilty unsuccessfully and trying to counsel him about staying away from such hard drugs, he left to continue scrounging up some money. I kept going, now a little bit more street-wise than before. The next stop was to get a new shirt and try to find a place to sleep (my shirt was bright white).

First Night

I ended up sleeping on a large downslope alongside a busy road in northern Portland overlooking the downtown area. It nearly froze that night and I was afraid to fall asleep and roll down the incline hundreds of feet into who knows what.

Thankfully, I survived the first day and night, which ended up being more difficult than I imagined, although my Cannbis-filled mind wasn’t really anticipating much beyond the next moment.

Being down on my luck from bad choices and circumstances combined with youthful ignorance and a country-boy mentality wasn’t working in my favor for living on the streets of Portland. I did realize how grateful I was to have my Huffy rather than the gas-powered scooter, as that machine would have attracted way too much attention.

I reverted back to my Air force basic training mode, be silent and anonymous, and don’t get attention.

The Abbey Hotel Dump

While I cruised around Portland for the first time in my life on my Huffy, I noticed all the homeless people along the Burnside Bridge. They were basically living right on the sidewalk in their sleeping bags, as many of the homeless services were on the west side of the bridge in the downtown area.

I realize Portland isn’t Mexico City or New York City, but to me, it was a massive place full of innumerable people. Eugene was a large city for me, so this place was massive.

Not knowing what to do and being over my head, I decided to scope out some cheap hotels.

The hotel I found was called the Abby Hotel; it was right in the heart of downtown Portland off Burnside St. What a complete dump this place was; it was awful beyond belief. The dire, dilapidated, depressing, and putrid place was about the worst place I’ve ever spent time in.

I’m guessing most prisons are nicer because people have to clean the bathrooms there. In fact, I later found myself in the Portland prison and can tell you it was much nicer, but that is another story.

To be honest, the big city was intimidating and I was second-guessing my decision. As someone who liked to mull things over, I decided to spend most of my money and stay there for a week — it was very cheap compared to regular hotels, around $200 a week back then.

The good part about the Abbey was being able to bring my bicycle inside and into my room. The elevators, hallways, and rooms all had large ceilings and were spacious in this regard. The rooms were small with only a metal spring bed and an old thin mattress I was weary to lay on until I passed out with exhaustion.

I remember, as awful as it was, getting in my room that first night and smoking a joint. I had about $80 worth in storage and would bring a nugget with me on my daily ventures. This first night though, sitting there alone, hearing the sounds of the big city around me, that joint really helped comfort and calm me down.

Food Card and Flipping a Sign

The show must go on though and once I woke up the next day there was no time to waste. Having only about $7 on my food stamp card and my benefits expiring that month, I couldn’t even rely on having food. The most amazing thing happened though, as I checked my account to find it was filled with around two hundred dollars!

This food money was the first break I had in Portland; I was so grateful that I went and bought a bag of food and gave it to a homeless man down near the Burnside Bridge area. It was early, he was just waking up and I gave him this big bag of goodies, he was very grateful.

It was me and my Huffy in the big city and I didn’t have a clue about what I was going to do. Of course, looking for a job was a good start, but this was before smartphones and I didn’t have internet access. I looked in the newspaper and scoped out some janitorial companies in the yellow pages.

After a couple of days of having no luck and running out of time in the Abby, I was getting desperate. It didn’t help that my Huffy was slow as molasses and always getting flat tires.

One day I was so fed up with the Huffy, that while pushing it down the street I just pushed it as hard as I could in a fit of rage. Right away I realized what a stupid thing I did, after it was wobbling down the sidewalk at full speed, precariously leaning toward the parked cars along the sidewalk!

Thankfully it hit something to stop it before it smashed into some nice vehicle. The stress was getting to me, I had to stop and smell the roses.

Later, I found myself for the first time holding a cardboard sign on the side of a street, explaining how I was a veteran and needed some help. I didn’t get any money and felt ashamed when some young people came by and looked at me like I was a loser.

The Golf Course Job

That wasn’t a very good option, so I reorganized and sought out some more employers to apply to. One of the main jobs I wanted to get was to work at a golf course, so when I saw an add for a cook at a golf course I went to apply, although I was totally inept in the kitchen.

Riding my Huffy about 5 miles across town to the golf course was a task in itself, but when I arrived and saw the kitchen area and the people working there, I realized it wasn’t something I could do as a homeless person.

Frustrated, I didn’t even apply, but I decided to go up to a man working there wearing a cowboy hat near the golf range and ask him if they needed any help. What happened next changed my life.

This nice man with a country accent and a cowboy hat looked at me in the eye and said “well, yes we do need a cart attendant, someone to sign out the carts.” I was more than willing to do this exact thing and I ensured him I could do the job, yes sir!”

On that wonderful day, I got my first golf course job with a handshake, a good word, and a stern look in the eye. I went back in and filled out the application with his assurance I had the job and showed up the next day and the rest of the year on time and ready for work!

The Formal Bicycle Years Had Begun

After knowing I had the job from this old timer and his good heart, I finally was able to experience Portland on my Huffy bicycle with joy in my heart. The bicycle years at this point had officially begun!

The ride back to my dim and dingy studio was like heaven, as I stopped in the bushes and smoked a celebratory joint. No drug test, working outside, and working at a golf course was more than I could have asked for just a day before when holding out a sign and asking for change.

The course I worked at was outside of the city some ways in the northern area, so I was able to enjoy the natural surroundings on my ride home once again feeling like a productive member of society.

Maybe it was just a part-time cart attendant job, but to me, it was as good as being a top writer on Medium and making ten thousand a month!

To Be Continued

For now, this is part one of the bicycle years series. The next installment will include getting another bicycle, which is when I really started enjoying riding a bicycle instead of a car in one of the most bicycle-friendly cities in the U.S.


Originally Published at Medium Dec. 16, 2022


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