I’ve been trying to find the right words for weeks—words that express concern without sounding combative, that challenge without condescending. I love Portland. I’ve built a life here. I’ve built businesses here. I’ve hired hundreds of people here. Oregon is my home.
And because I love it, I have to be honest.
Something is off.
This weekend, tens of thousands of people flooded downtown Portland to protest ICE and the No Kings initiative. The turnout was massive. The energy was electric. The civic engagement was real. Whether or not I agree with the cause, I admire the passion. The right to assemble and raise your voice is a cornerstone of democracy, and Portland has long been a place that takes that responsibility seriously.
But just a few days later, I walked into an office that used to buzz with a few hundred employees. It was nearly empty. Maybe ten people there—maybe. One of the leaders told me that it’s a struggle just to get folks to come in, and when they do, it’s usually for the free food. They show up. They eat. They leave.
That contrast has been living in my head all week.
On the one hand: a city fully alive with cause-based energy and civic expression.
On the other: a city quietly fading in its willingness to build, to create, to work.
We are wildly engaged in activism—but increasingly disengaged from productivity. We show up for protest—but often ghost our places of employment, collaboration, and economic contribution. We care deeply about what’s wrong with the world—but seem less compelled to invest in the long, hard work of making things better from the inside out.
Let me be clear: activism is essential. We need voices raised. We need movements. But we also need builders. Makers. Doers. We need people to clock in with purpose, to lead teams, to mentor colleagues, to return to the offices that once gave our downtown its rhythm and energy. We need people to show up for work with the same fire they bring to the streets.
Because the truth is: protest without productivity doesn’t lead to progress. The change we seek in society doesn’t just live in signs and chants—it lives in small business growth, in job creation, in tax revenue that funds services, in companies that reflect the communities they’re built in. It lives in showing up.
The cost of living in Portland is high. Housing is expensive. Energy is expensive. Coffee is $7. And yet we seem hesitant—even resistant—to support the economic infrastructure that makes it all possible. The imbalance between what we ask for and what we contribute is growing wider by the day.
And it’s not because people don’t care. Quite the opposite. Portland is filled with deeply caring, engaged, values-driven citizens. But somewhere along the way, our culture has started to tilt. We’ve begun to conflate social consciousness with social media. We praise disruption but undervalue discipline. We reward critique but rarely celebrate creation.
I’m not here to blame. I’m here to ask us to see it. To pause long enough to recognize the pattern. To ask whether we’re building a city where future generations will thrive—or simply inheriting our disconnection.
Portland isn’t broken. It’s just out of balance.
And I believe we can fix it.
That’s why I’m still here. I’m not giving up on this place. I still believe in Portland’s potential. I still believe in its people. I believe we can find a way to hold both activism and productivity with equal care. I believe we can create a culture where we show up not just to protest what we’re against—but to build what we’re for.
That’s the Portland I want to be part of. A city of conviction and contribution. A city of values and velocity. A city that protests with purpose—but also builds with pride.
If that’s the city you want too, then let’s go make it.
Together.
If today’s episode made you pause—if it reminded you that we can care about the world and still show up for work, that we can protest and still produce—share it with someone who’s ready to build a better Portland.
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Until next time—show up with conviction. Lead with purpose. And remember: progress comes from those willing to do the work.
Let’s build the Portland we believe in. Together.
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