an ode to Portland
There have been stretches of my life where, on one hand, I seemed to drift aimlessly, and on the other, was quietly being pulled along by the invisible currents of destiny. For years, Portland was like a revolving door, a city I kept falling into and stumbling out of, as though it were a cosmic waypoint along a route I didn’t know I was on. Over and over, as if the city itself were some quiet accomplice of the universe wearing the mask of a stern teacher, luring me back into a game I could never quite solve. I fumbled through it, convinced I had what I needed, only to find the missing pieces scattered just out of reach. And each return offered another shard, another lesson tucked beneath the moss and rain, one I hadn’t even known I was missing.
I first arrived in Portland when i was 24, just one day after a suicide attempt that followed four months on the Pacific Crest Trail.
That journey hadn’t just left me in a daze, it stripped me down entirely. I felt hollow, like everything I thought I was had slowly been unraveled along the trail. Stepping into Portland felt unreal and groggy, like just waking from a dream. Only to realize the dream wasn’t in fact a dream, rather it had always been my life, woven around me since birth, and now, for the first time, I was beginning to see there was no waking up. And just a few days after arriving, as if i didn't feel weird enough, I left for my cousin’s funeral, who had, unlike me, succeded in committing suicide. Leaving me utterly flailing in the deep end, drowning in confusion and deepening the sense that something beyond me was in motion.
I returned at age 26, after an emotionally testing winter ski bumming in Breckenridge, Colorado, i was longing for love so much that i was willing to exchange my life for it. As “chance” would have it, that love happened to live in Portland, where i returned for a short, two-month stint, drunk on the idea that love will solve all your problems. Although it solved some, it also created more, sending us on a humbling escapade through Europe, where we ended up in Chicago with my tail between my legs swearing never again.
Age 27, year 2020. We all remember 2020 don't we? I boarded the plane for Portland just as the pandemic began to unfold, in fact, ole Trumpy poo declared the national emergency speech just as we were taking off.
Perhaps it was an omen, one I failed to recognize at the time. After all, I hadn’t wanted to move to Portland; I was walking my lover’s path, not my own. Naturally, it didn’t take long for it to unravel. Six months later, we were evicted.
With nowhere else to go, we ended up in a tiny, rustic shack in Breckenridge, Colorado.
No running water, no electricity just a wood stove and a roof over our heads. From there, we drifted to Flagstaff, where a gracious friend let us sleep in their woodshop. As winter rolled in, we returned to Wisconsin to wait out the cold, saving enough money to buy a car and, once again, head west, led not by personal desire, but rather by the same force that had guided so many of my moves: love.
By spring of 2021, I was yet again back in Portland, yet again signed a lease in the city i didn't want to be in and yet again within five months, we were evicted. When will i learn?
For the fourth and final time, I found myself back in Portland, once again signing a lease in a city I didn’t even want to be in, and once again, within five months, we were evicted. Over the next year and a half, I bounced around: first living with one of my best childhood friends in St. Johns for six months, helping them renovate and move to a new home in Yacolt, WA; then six months living out of my car, Ravie; then six months in Southeast, staying with someone whose venom still lingers in my memory. Eventually, I landed gracefully in what would become my final year in Portland, grounded, consistent, exactly what I had been yearning for, and yet, it would lead me into the heaviest days I’ve lived on this earth.
And so what, who cares. I asked myself “why i feel the need to share my chronological odyssey with Portland in the first place?” “WHO GIVES A SHIT?”
Maybe it’s just my ego, delusional, per ush, thinking this nomadic, hero’s-journey life is somehow noble. Cinematic. Like I’m the tragic lead in a movie only I’m watching.
Or maybe it’s not ego at all.
Maybe it’s me entertaining the idea that a city can be alive. Not just metaphorically, but actually alive. A breathing, sentient thing. That Portland, beneath her piss-soaked sidewalks and broken windows, isn’t just concrete and chaos, but consciousness, manifested in asphalt and sirens. A frequency. A presence.
It felt like she wasn’t just a backdrop, but a being. And she spoke constantly, but in a language we’ve forgotten how to hear. In the screams of addicts echoing through alleys. In the caws of a murder of mangy crows lined up on the telephone wire and in the smash of your car window at 2 a.m. In her own twisted way, she was always talking.
She cried with the rain.
She bled through the open sores of the unhoused.
And the relationship you can have with her?
It’s real. Just as real as one with any human. Just as raw. Just as complicated.
If that’s true, then Portland wasn’t just a city to me, she was a friend. A harsh one. A mirror. A teacher. One who unapologetically held me accountable for becoming who deep down I knew who I wanted to be. Every flat tire, every gut punch, every spiraling thought loop and broken window wasn’t just some random inconvenience. And it wasn’t punishment, either.
It was initiation.
Not because I was special. But because that’s how transformation happens. Growth isn’t neat. And pain, it’s never just yours. That’s the thing. Pain feels personal, but it’s not. It’s shared. Archetypal. Woven into every human being’s contract.
We all get dragged through the mud, just in different ways. Grief. Doubt . Identity collapse. Existential dread. These aren’t unique to me. They’re universal patterns, ancient currents we’re all dropped into at some point. The monsters we meet look different, but the battle is the same. And for me, those monsters happened to wear the face of a foggy city with graffiti and vegetation bursting through the cracks in the sidewalk.
Looking back now, Portland broke me. But she also put me back together. She trained me, mercilessly. Beat the hell out of me with metaphorical brass knuckles and steel toe boots. But her cruelty had a strange kind of wisdom to it. Like some old mystic crone leaning against the bricks behind a dive bar, smirking, “Ohhh, you thought you knew what was coming did you? You thought you were ready huh??,” before disappearing into the steam of a storm drain.
Sometimes it felt like Ender’s Game, like I was inside a simulation designed to push me past who I was, fast and without explanation. And Portland played every role: the battlefield, the enemy, the mother, the mirror.
Maybe cities, like people, carry frequencies. Maybe Portland is one of those places that gets broadcast to the world as chaos, burning dumpsters, riot footage, broken glass and human shit on the sidewalks. But maybe it’s not just dysfunction. Maybe she’s vibrating ahead of her time. Maybe the chaos is the wake-up call. Maybe she’s trying to stir something ancient in us, something sacred we’ve forgotten.
Like she’s saying: Wake up, you idiots. This isn’t about comfort. It’s about becoming.
So yeah, I guess this is my love letter.
To Portland.
To the teacher hiding in plain sight.
To the city that broke me open, and in doing so, gave me back to myself.
Thank you.