It's Friday afternoon in front of Voodoo Doughnut, and a long line of tourists bears sweltering 90-degree heat for 45 minutes to spend $20 on a pink box of gluttonous confections topped with Froot Loops or bacon. Swirling around them, the full spectrum of Portland's transients.

Next to a solar trash compactor, a shirtless man is passed out on his side with a sign that reads, "Too honest to steal; too ugly to prostitute." A circus of gutter punks with leathery sunburnt skin and greasy overalls holds signs asking tourists for weed money. Down the sidewalk, a young married couple with dreadlocks and a beagle plays Depression–era folk songs behind an open guitar case.

A man in a black tank top and jeans with buzzed hair and an athletic build rolls up on a bike with a sleeping bag and sweatshirt tied to the back. "Bottom of the Barrel!" he says, calling the band by name. "I just drew you guys last night!"

The man flips open a small book bound in black leather and reveals a pen sketch of the duo that resembles a friendly marriage of Shel Silverstein and Ralph Steadman. The book is filled with sketches of the landscape of downtown Portland, transients and all. He introduces himself as Jake.

"This is 'Project Portland,'" he says. "I'm sleeping on the sidewalks and rooftops, focusing on the transitional period of how people ended up out here."

This, I realize, is a man I need to talk to. Since dropping anchor in Portland a month ago, I've made little progress in narrowing the chasm between myself and those who don't even have a repurposed van to fall back on. My attempts to help the people who call the streets home—giving spare change, doing a little volunteer work—haven't helped me close the gap. In Jake's illustrations, I see the outlines of a bridge—and the shadows of people sleeping on it. I ask if he wants to meet up for pizza.

Jake Koopmann's air of enthusiasm goes beyond the West Coast propensity to be casually stoked about everything. His optimism belies a rough patch in Yuma, Ariz., that he conquered by getting sober and leaving a 15-bed group home in the desert. After getting laid off from Columbia Distributing in Portland in late 2012, he did maintenance work in exchange for rent at a world-renowned glass-blowing company in Eugene.

"I came up here one night to draw the bridges," he says while flipping through the book, landing on a picture of a guy sleeping on Northwest Broadway near the Pearl District. "I drew this guy, and I woke him up to show him. He was totally blown away that someone would stop and take the time to do that. He didn't even care that I woke him up."

A few minutes later, Jake chose to live on the streets. "My girlfriend decided to come up and wanted me to meet her parents," he says. "I didn't wanna do that, so I decided, 'I'm gonna rough it. I'm gonna stay out here and draw until the sun goes down.'"

He's been sleeping on the streets of Portland for the last month, sometimes on rooftops, sometimes outside City Hall. Jake is homeless, but he knows there's a bold distinction between himself and the subjects he draws.

"Homelessness is more of a temporary state. Wherever you lay your head at night, that's your home," he says. "Haplessness is when you lose all hope. You have no self-worth, no drive or motive to do anything. That's when you're lost. You can give a hapless person money or a job, but they'll be back there with that sign the next day because they don't think they deserve to get straight."

We finish our pizza and discuss our generation's eagerness to take on debt to service the lifestyle we've felt entitled to since birth. I tell Jake that I chose to live in a van to avoid the financial whiplash of adjusting to a new city. "Everyone out here is just like me or you," he says. "They're mothers, fathers, brothers and sisters. We're all one step—one accident—away from being right there, too."

As I pedaled back to my van, I considered the haunting sketch Jake drew of the man asleep on Broadway and Jake's simple artist's statement: "He was a human and he deserves to be acknowledged."

Reminded of where I stand on the chasm between the haves and have-nots, I feel momentarily ashamed. Then again, there is no chasm. We share the same streets, sleep under the same sky. We're all in this together.

VANIFEST DESTINY: Pete Cottell lives in a van and writes about it at