Why I'm Leaving Portland

The city is empty. Look at these pictures. All taken between four and five PM on a Monday, but that’s kind of what I was going for: what is the city like without tourists or people coming into town from the suburbs? Who lives and works here?

Very few, as it turns out—or they’re all inside. Incredibly sad to see. It didn’t used to be this way. The city used to throb with life and people and businesses and restaurants and students and artists and tourists.

I was born here, and for all but two years in California and a few more spread between Salem, Eugene, and a brief stint on the Oregon Coast, I’ve lived my entire life in Portland or the metro area. I’ve lived in every quadrant of the city—NE, SE, NW, and SW—as well as a few of the suburbs: Tualatin, Beaverton, and Tigard.

The city itself—the buildings, the green of Forest Park to the northwest, the way Mt. Hood dominates the eastern skyline, the quirky neighborhoods all rolling down to the lush waterfront—is beautiful. It’s so, so beautiful.

But Portland’s character now is Ugly. People hustle quickly from building to building, don’t make eye contact, don’t smile, loath to talk to someone on the street, even if just to wish them a good morning. Probably because every few blocks or so, you’ll get screamed at by a homeless person who belongs in recovery or a mental ward, or accosted by a panhandler begging for money to feed his dog or his next fix. Many of the people who have jobs are mean now too: gruff, angry social activists baptized in the poison of identity politics and safety-ism, defining their lives through status hierarchies and trauma and victimhood; the kind of people who spend too much time online and believe atonement rests in cancellation and virtue signaling.

Don’t get me wrong: we still have our lovable weirdos and high-flying executives and marvelous mavens of entertainment and industry. The city regains some of its vigor and vivaciousness when there’s a big conference or concert in town, a festival on the waterfront, or the run-up to Christmas and New Year’s.

But as Galadriel says in LOTR, “much that once was is lost.” Not because none now live who remember it, but because for too long, too many Portlanders refused to admit there was anything wrong—some still won’t—and even now that it’s obvious, no one with power is willing to unleash the force and vigor and follow-through it would take to solve the city’s problems.

Tina Kotek, Keith Wilson, feel free to give me a call. I’ve got some ideas. Or you know what you could do? You could travel to cities in the U.S. where they don’t have these problems and ask the leaders there what they do to keep their streets clean and economy thriving, and then do that instead of whatever current fuckery we’re trying here.

Just sayin’.

But then, what did we expect? This is what happens to a city—or in any situation, really—when you have no adults in charge.

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Yesterday, as I was walking through the apocalypse this once-fair city has become on my way to a date, I stopped at a gas station on MLK to get a bottle of water and some gum. I asked the cashier, “Are there always this many maniacs around?” He said yes, nodding at a man raving at a trash can outside as if on cue, and we talked a bit in agreement about how bad things had gotten. Behind us, two androgynous zoomers shook their heads. “Fucking boomers,” I’m sure they thought. We used to attract talented artists and chefs and entrepreneurs and adventurers, but now these types are all we get.

And despite this portion of Zoomers—the sterile, phone-addicted, trauma goons who came of age during COVID—being the most helpless generation humanity has yet to produce, I feel bad for them. Because life doesn’t have to be a sexless, joyless, hopeless, childless experience where you tolerate a city full of homeless, drug-addicted zombies and believe we should all do nothing but hug our knees and catastrophize what to anyone else would be seen as ordinary life challenges.¹

I feel bad for them because it’s not their fault: they never had real adults in their life. They had parents, surely, but no adult allows their child to become the kind of spineless worms these kids have become. Real adults teach their children that life is hard, that it often isn’t fair, and that we have to work to build resilience, a strong work ethic, and gumption if we want to be successful. They also show their kids that life is rewarding, full of meaning and beauty. And while good parents encourage their kids to be whoever they want and support them always, adults don’t tolerate nonsensical bullshit, like the idea that gender is fluid or that everything now is terrible.²

And if you look closely, you’ll see that the Gen Z kids who were raised by adults are doing just fine: partying in college, becoming crypto millionaires or influencers or enterprising entrepreneurs, or just working ordinary jobs and enjoying life the best they can like normal people always have and always will.

Similar to those lost Zoomers, Portland hasn’t had an adult in its life for the past 20 years. It’s become an unredeemable mess because a majority people who live here are willing to tolerate it—because they care more about our mayors’ and governor’s progressive accolades than their ability to do the basic job of keeping the city clean and habitable, or heaven forbid a good place to own and operate a business. The people of Portland, collectively, have not behaved like adults, and as a result we haven’t had adults in the Mayor’s office or in Salem for that matter, for a very long time.

Because if we had adults in power, they would’ve said: “No, you can’t jack up on the street; no, you can’t have a grow lab in the alley; no, you can’t break into cars and get away with it; no, you can’t set up your tent anywhere you want; no, you can’t fire professors because they actually believe in science and say so; no, you can’t smash the windows of businesses; no, you can’t spend all day every day screaming at people on the streets; no, we’re not going to defund the police or allow lawlessness without consequences.”

The number of businesses who’ve closed or fled downtown Portland grows by the year. Legendary places like Pok-Pok, Bailey’s Taproom, Toro Bravo, Bit House Saloon, and Paley’s Place. We’ve also lost Nike, Target, REI, and many other retailers who once called the city home. Our largest office tower is half empty because no one wants to work downtown.

For the last two years, I lived in a suburb, Beaverton, and on the surface it appeared Portland had gotten slightly better. I can now confidently report: it has not. It is lost. At least a third to a half of the people you see will be homeless, and one-third of those will scream at you or ask you for money or accost you in some other way as you’re trying to go about your business.

You know who I’ve seen very little of during this recent stint in the city? The police.

As for the homeless, I wish we did more for them. I wish we had more housing and a functional healthcare system where people could get counseling and treatment for addiction. I wish we had some hospitable and humane way to rehabilitate people who’ve become homeless and help them get jobs and apartments so they don’t have to live on the street. Too often we forget they are people, deserving of the basic dignity and respect we would afford anyone. Too often we forget that very few of them chose this path. I’ve doled out at least $100 in the last week in 10’s, telling my recipients to “get some food, take care of yourself.” It’s what my faith and humanity require, but it’s unfortunate it’s so necessary. And of course, it’s not nearly enough. But we can’t help everyone. The problem is too big to solve through the kindness of individuals.

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Unfortunately, homelessness isn’t Portland’s only problem.

It’s also extremely expensive. The average cost for a three-bedroom home in the Portland metro area is around $600,000. The average cost for a two-bedroom apartment is around $2,000 per month. All for the privilege of living in or near a city where going outside even infrequently guarantees you’ll see stuff like this on occasion.

I get why people live here if they have to stay: got into their home when it was a third of the price and/or are locked in a low mortgage, and/or can’t relocate due to their job. And the suburbs are still mostly nice. But I honestly have no idea why anyone wants to move here, and I can’t understand why you wouldn’t leave if you could.

My family has been here for six generations—my ancestors literally came over on the Oregon Trail. And, as fate would have it, I’ll be the first in the family to end that legacy. Because I’m out. I don’t have to live here anymore, and I’m not going to.

I honestly can’t leave fast enough.

If you’re wondering, my next stop is Boise. It’s clean, beautiful, vibrant, and the people there are some of the friendliest people I’ve encountered anywhere.

I considered Seattle, San Francisco, and Sacramento—all within the region I manage—but those cities have the same problems Portland does. Pervasive homelessness with no end in sight, housing that’s outrageously expensive. I will note, however, that in terms of the homeless problem, Portland is by far the worst—it’s actually not close—and I know this for a fact because I travel to those other cities all the time as part of my job. Whatever they’re doing is at least slightly better than what we’re doing here.

So anyway, sayonara Portland! I loved you once, and I’ll always think fondly of your epic skyline, the way you used to shine so beautifully, and all the incredibly wonderful humans I’m leaving behind.³

Hopefully some adults will come soon to care for you, but I won’t be around to see it.

Peace!

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1. BTW, if you’re in this cohort, it doesn’t have to be this way. There are other choices and you will be OK if you choose to do something different.

2. Obviously, some people truly do experience gender dysphoria, but many of the parents of Zoomers encouraged their kids to question their gender, and indulged it when it should have been obvious their child was not gender dysphoric. That is a tremendously cruel and dangerous thing to do; no adult would do this to their child.

3. Don’t worry family and friends, I’ll visit often!