I’m hunting apartments in Portland and wrestling with whether to upgrade my place or upgrade my life by leaving a city that feels more extreme than home. This piece traces the push and pull of roots, safety, social exile, and the strange comfort of familiar rain against the urge to find someplace calmer.
I’m looking at new apartments this week in Portland, Oregon because it’s time for an upgrade and the city hasn’t exactly gotten quieter. Hunting for a new place turned into a bigger question: if I move anyway, why not pick a different city or state? The obvious pull is toward quieter streets and friendlier politics.
I grew up here and have always felt a soft spot for Oregon’s tall trees, steady drizzle, and the misty coast. Those things are part of why I’ve returned again and again between stints in New York and Los Angeles during my most productive years. Portland used to feel like “my place,” and that makes the decision to leave feel personal.
Over the last decade and a half, Portland’s mood shifted into something raw and intolerant; it’s affected daily life in ways I didn’t expect. The artistic circles I used to enjoy now feel like echo chambers where disagreement is unwelcome. When people discover I’m conservative, the social temperature drops fast and a lot of doors quietly close.
That exclusion hit hard during the years around #MeToo, the pandemic, and relentless anti-Trump fervor. I lost roughly 80 percent of my writer friends and about half of my other pals, simply because my politics didn’t fit the script. Social life warped into a kind of desert island existence where gallery openings and literary parties feel off-limits.
Once, I even skipped the celebration of life for a literary mentor who had helped me early on; the shame of that still stings. I owed him a lot and not being able to attend felt like a moral failure born of social fear. The absence of those communal rites makes staying feel lonelier than it should.
Right around then I saw a TikTok from a woman whose family moved from Seattle to Wyoming and she said something that landed: “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.” That clip forced me to ask whether inertia and comfort with bad vibes had trapped me here.
I worry about fitting in if I move to a red state. Boise, for example, is clean and orderly, with fewer visible homeless and a strong family and church presence. I’ve visited and liked the people, but I keep wondering if my urban tastes, obscure music, and bookish humor would land there the way they do in a big liberal city.
Then there’s the friend who moved to Florida during Trump’s first term and seemed reckless at the time; he emailed updates, fell in, and loved it. Watching him settle makes me think my hesitation looks a lot like missing an obvious opportunity. Ten years from now, his move could look like common sense while I’m still debating uprooting.
Part of me imagines a life without the constant confrontation on the street and at city hall, the quiet streets and more ordinary evenings. Another part misses the rain, the trees, and the weird little cultural ecosystem that only a place like Portland gives you. That tug can be as persuasive as any promise of safety or sanity.
History keeps popping into my head — people who stayed for roots, people who left for new ground — and there’s no simple rule that fits every life. I’ve hoped the city’s extremes would mellow over time, but reconciling that hope with daily reality is harder than I expected. So the question remains: do I stay and keep trying to claim a corner of this city, or go where life looks and feels more stable?
