Over the last few weeks, I’ve told you a lot about my business; what’s been going on, what we’ve been dealing with, what it’s taken just to stay afloat during what is, historically, the hardest time of year.

And as I sat down to put together a year in review; our accomplishments—I realized how complicated that word has become for me. Because when I point to our accomplishments, I mostly point to the things people write about us. The kind words. The recognition. The love from our community. All of it real. All of it deeply appreciated.

And yet, at the same time, operating in this part of town, more specifically, in a neighborhood that has undergone dramatic change over the last five years—it’s been hard to feel inspired. Hard to feel excited about what a new year is supposed to promise, given the very real mess we find ourselves in.

Let me rewind for a moment.

There’s a term you’ve probably heard by now. The so-called doom loop.

I should say this upfront: my perspective is probably skewed. I live in the data. I look at our numbers; how our business has changed, how the city has changed alongside it. I look at patterns, not anecdotes.

You see this everywhere right now. People talk about the wine industry struggling because Gen Z “changed the way they drink”—as if Gen Z is the only generation drinking wine, or not drinking wine. It’s an easy explanation. A clean one.

For us, it’s been similar. I trust the numbers, and not the statements by those who every-few-months visit downtown and follow it up with a declaration that things “look better.”

For a moment, they did.

In 2024, I started to believe it. I saw it in the data. Little by little, things were coming back.

The truth is, I don’t have a memory of the “good old days.” I’ve only operated in this industry post-COVID. Before that, I was just a fan. Of the industry. Of the city.

And I still am.

But it’s different now, not because I stopped loving Portland, but because I’m exposed to more information. My information. The numbers that come in every day. And just as importantly, my commute.

I live downtown. I always have. I love it here. Let me rephrase, I love the idea of living here. I love walking to a coffee shop. Walking to the theater. To dinner. The energy of a Saturday at the PSU farmers market. Broadway on a night when something great is in town. Pioneer Square when it’s alive.

That energy still matters to me.

But I’d be lying if I said it hasn’t changed. And I don’t see that change in headlines—I see it every day. On my walk to work.

Houselessness. Open drug use. Streets that feel neglected and unsafe. I don’t encounter this occasionally. I see it four or five times a day.

Think about that.

I don’t just see it on my commute. I see it outside my door. Ask me for the number for Clean & Safe—I can recite it from memory. That’s how often we have to call.

Over the last year, the term doom loop has become attached to Portland—fairly or not. When I first read about it, things started to line up in a way that was hard to ignore.

A change in local leadership. A downtown economy that wasn’t rebounding at the pace many of us hoped. And an approach to governing that, while well-intentioned, felt increasingly singular in how it framed both the problem and the solution.

Shelter beds became the symbol.
Fifteen hundred of them.
A clear target. A deadline. A number you could point to.

And to be clear, adding shelter beds matters. It’s necessary work. But somewhere along the way, that number started to stand in for progress itself. As if meeting a metric could resolve a problem that is far more layered, far more human, and far more visible than any single goal could capture.

The challenges facing this city aren’t singular. You could make a long list. But near the top of mine is perception; how people see Portland, what they believe about it before they arrive, what they repeat about it once they leave.

And like it or not, food, beverage, and hospitality are a big reason this city still holds relevance. People come here for a meal. A show. A night out. Something that reminds them why cities matter in the first place.

In theory, perception should be the easiest thing to change. Somehow, it’s been the hardest.

There’s no shortage of ideas. A baseball stadium proposal. New theaters. A music venue. The Broadway corridor. The Green Loop. Blueprints everywhere. Timelines. Vision on paper.

The problem isn’t imagination.

It’s execution.
And it’s trust.

When you look at the numbers; how many people are leaving, what we pay in taxes—it’s hard to ignore what they’re telling us. The tax burden here is high. It’s really fucking high. And that’s not opinion. That’s math.

We’re not leading the country in much of anything that affects daily life. Education outcomes near the bottom. Housing costs outpacing wages. A cost of living that surveys show is the number-one frustration for people who stay—and a primary reason others leave.

So when people ask why confidence feels fragile, why foot traffic doesn’t rebound, why businesses hesitate; it’s all right there.

Here’s the part that often gets misunderstood: Like many in this town, I don’t have a problem with being taxed more. I believe in contributing. Cities only work when people buy in. What’s hard to reconcile is paying some of the highest combined tax rates in the country and still feeling like the return is abstract—like the impact lives somewhere else.

And I don’t have a problem with how many people sit on city council. Eight. Twenty. Thirty. I don’t even need them to agree.

In fact, I’d rather they didn’t.

Disagreement is where accountability lives. Where ideas get tested. Where compromise forms. Friction isn’t failure; it’s how progress happens when systems are working.

But in a city that’s hurting the way this one is, leadership that feels largely aligned in worldview and approach doesn’t inspire confidence. It raises questions about rigor, challenge, and whether there’s enough internal pressure to course-correct when outcomes don’t match intentions.

That’s when the idea of a doom loop starts to feel less like shorthand and more like something structural.

Not because Portland can’t recover.
But because recovery requires systems willing to question themselves as much as they ask residents and businesses to keep believing.

So no, I don’t think Portland is doomed.

But I do think we’re stuck in something quieter and more dangerous than collapse. A loop where perception hardens faster than reality. Where metrics replace trust. Where goals are mistaken for solutions. Where the people who still show up every day are asked to keep believing without being shown much in return.

A doom loop isn’t a city falling apart all at once.
It’s a city losing its ability to correct itself.

I still believe in this place. I live here. I walk it every day. I stake my livelihood on it. That belief hasn’t disappeared—it’s just become more demanding.
Less willing to accept symbolism in place of substance.

Cities don’t survive on optimism alone. They survive on trust. On accountability. On the feeling that effort is met with competence, and contribution is met with care.

That’s not pessimism.
That’s responsibility.

And for a city that’s always prided itself on being thoughtful, creative, and human—this feels like a good place to start again.