Portland’s triumphant return to ridiculous decisions

If you’ve ever had the misfortune of being stuck in a room where I’m on a panel talking about Portland as a city and community, you’ve probably heard me mention Portland’s “ridiculous decisions.” And bemoaning the fact that we don’t seem to be making those decisions as often—or as boldly—as we did in the past.

I miss the ridiculous decisions. The ridiculous decisions built much of what we appreciate about Portland today. You’re soaking in them.

They were ridiculous decisions like:

And folks probably made a bunch of decisions that have long since been forgotten because they didn’t pan out so well.

But they still made them.

They were the types of decisions that were beyond visionary. Beyond disruptive. They were prescient of a future that few could see. And completely counterintuitive to the bulk of the population at the time they were made. They went against the prevailing wisdom. So naturally those decisions drew ridicule.

Looking back on them today, however, those same decisions draw praise and admiration. Forty years later. Because they were brave. And thoughtful. And insightful. And ridiculous.

This whole idea of ridiculous decisions came into sharp focus for me as I sat on the steps of the OMSI auditorium during TechfestNW in 2013, as Alan Webber—one of the people involved in helping plan the Portland in which we live today—delivered a call to action to attendees. It was a call to build the next great Portland.

And that’s when it dawned on me. We, the modern day Portlanders, were basking in the glory of decisions made decades before us. We were taking advantage of the thoughtfulness of our predecessors without paying it forward to those who would come after us.

We were coasting.

It became clear to me that we, as a city, needed to get back to our predecessors’ tendencies to make more ridiculous decisions, more often. We needed to make the ridiculous decisions, today, that—forty years from now—would result in a better city for future Portlanders. We needed to make ridiculous decisions predicated on the future we wanted to see, not dictated by the mores of today.

But I was stumped. Where could we make those decisions? Where was the opportunity? I wasn’t quite sure. Would it be education? Would it be healthcare? Would it be something else?

Turns out, it’s business. And investment. I think that’s where Portland is going to make our next ridiculous decisions.

It starts with things like business leaders searching for a better way to ensure an equitable and livable city. It continues with founders looking for new models of funding and growth, striving not to be unicorns but rather zebras. And it crystallizes for me—coincidentally at TechfestNW again—when leading investors like Rukaiyah Adams have scary conversations onstage in front of hundreds of attendees about rethinking the definition of “return on investment.”

The current system can’t be the end of the evolution, she said. Progress can be made by asking bigger questions of ourselves: “How can we deploy these trillions of dollars with the aim of taking better care of one another?”

I suddenly—and hopefully—feel that we’re no longer coasting. And that we’re getting ready to make ridiculous decisions again.

We may already be making them as we speak.

I’ve always been bullish on Portland. But now, more than ever, I’m greatly looking forward to the ridiculous decisions that will inform the future of businesses and investment in the Rose City. And I highly encourage you to start chasing those ridiculous decisions of your own. Portland will be all the better for it.