I’m looking at new apartments this week here in Portland, Oregon. It’s time for an upgrade.
This has triggered a debate I often have with myself: If I’m going to move, why not leave dysfunctional, far-left Portland altogether?
Had I become so comfortable with the bad vibes of Portland that I would stay here indefinitely, out of inertia or laziness or not wanting to start over?
This is my chance to move to a different city. Or another state. Somewhere with fewer drug addicts and criminals roaming the streets and fewer democratic socialists roaming city hall.
I grew up in Portland. I have lived here off and on throughout my life. During my most productive years as a writer, I lived in bigger, more media-oriented cities, mainly New York and Los Angeles.
But I’ve always loved coming back to Oregon and assumed I would settle here when I retire. Portland always felt like my place. I love the tall trees, the gentle rain, the misty Oregon coast.
Free radicals
Unfortunately, over the last 15 years, Portland has become a hotbed of radicalism and political intolerance. So much so that it has affected my daily life.
I’ve always socialized with creative types. But in Portland, the artistic community is often more hysterical than the violent protesters in the street.
Once it became known I was conservative, I lost about 80% of my writer friends. And maybe half of my other friends. This social exclusion was especially bad during the years around #MeToo, and then COVID, and of course the constant presence of Trump derangement syndrome.
Un-friendzoned
The result is that living here has been like living on a desert island. I feel unwelcome at art events. I avoid literary parties and gallery openings.
One egregious example: I didn’t attend the celebration of life for one of my most important literary mentors, a beloved Portland poet who encouraged me as a young writer and helped advance my career.
I owed so much to this man, and I couldn’t go to his funeral!
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Michael Ochs Archives/Getty Images
Tiny bubbles
Recently, I saw a TikTok video by a woman whose family had moved from Seattle to Wyoming.
Her message was simple: “No matter how much you think you are aware of the bubble you live in, when you get out of these far-left cities, a whole new world opens up to you.”
This hit me hard. Had I become so comfortable with the bad vibes of Portland that I would stay here indefinitely, out of inertia or laziness or not wanting to start over?
My own private Idaho
One reason I’m reluctant to move to a red state is I’m not sure I would fit in.
Take for example, Boise, Idaho, the closest red city to Portland. I’ve visited there many times. It’s clean. There are no homeless. The people are super nice. It’s very “churchy” and family-oriented. There’s a large Mormon population.
But could I adapt to such a place? I’ve lived in liberal cities MY ENTIRE LIFE. I have never lived in a place like Boise. Would I find people who understand my sense of humor? People who like the obscure music I listen to? Or read the books I read?
Yes, the people of Boise would share my core values. But would they share my urban tastes?
Go east, young man
I had a Republican friend here in Portland who moved to Florida during Trump’s first term. At the time, that seemed like a drastic change.
For a couple of years, I emailed him every few months to ask how he was doing. He had settled right in. Florida was great. He loved it there.
As he grew more comfortable in Florida, I grew less comfortable in Portland. Now, in 2026, moving to Florida 10 years ago seems like a genius move. I am humbled by his foresight.
The great escape?
So what should I do? Be the latecomer, arriving in Tampa or Austin or Nashville a decade after all the smart people already moved there?
I guess it’s never too late. I could still escape.
But what about the tall trees, the gentle rain, and the misty coastline I love so much? What about my roots in the place where I grew up?
Robert E. Lee didn’t abandon his home state of Virginia in the face of a civil war. But Virginia was famous for its proud history and strong cultural heritage.
I’m from Portland, famous for people with orange hair who don’t know what gender they are.
Fall into the gap
I’ve always assumed Portland’s current political extremism would fade over time. Sooner or later, people would calm down and return to some form of normalcy.
But whenever I try to connect with my former liberal friends, I quickly learn that the derangement is stronger than ever.
So, should I stay or should I go?
These are the decisions we have to make during these difficult times — as we struggle to maintain our sense of ourselves and of where we came from.
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