I spent seven years as a Portland tour guide. It was my job to escort groups of tourists through Downtown, Old Town, and the Pearl District and professionally yell facts about whatever was in the area. That job, professional fact yelling, changed my life.
I was born in Portland in 1980, grew up in Northeast, and went to Lincoln High School as a magnet student. In high school I was the kind of kid who skipped class to hang out at coffee shops. My friends and I talked about how Portland was great. We also talked about how Portland sucked.
Portland was great because it was easy to live here. Portland was uncrowded and okay-smelling, and we had a nebulous idea that we were good at something called “urban planning.”
But Portland also sucked. Other American cities seemed to have a definitive identity, and Portland didn’t. We weren’t an important grunge hub like Seattle. Ours was just a fairly pedestrian town/city of little import, and that perceived lack of status bugged the hell out of me back when I was an angry teenager.
I left. I went to college (in the distant land of Eugene), lived abroad for a while, and moved back in my late 20s. I became an unlicensed teacher, got laid off, and found a tour guide job on Craigslist. That was in 2010, and it ended up being one of the most formative gigs of my life. I learned more than I ever thought I would about the city I used to complain about. I learned that teenage me was an idiot and that this place does have a sense of identity. And I learned it by seeing my hometown through the eyes of a tourist.
I gave several different kinds of tours, but for the most part I’d walk people through Downtown, where we’d talk about planning, transportation, and mostly positive stuff. I also took them through Old Town, where we’d talk about crime, homelessness, and racism.
The vast majority of people on my tours were on vacation. People who are taking time off from work or are on their honeymoon are predisposed to having a good time—so talking about the positive stuff was easy. If someone’s in vacation mode it’s very easy for a tour guide to tell them that something is good, and they will agreeably think it is good. (You should probably know that I tend to drift toward contrarianism—so if there’s a thing a lot of people like, I will look for reasons why it is actually bad. It’s something I do.)
But here’s the thing: Portland actually does have a pretty functional urban core. A big part of my job was reading up on how Portland went from being relatively dormant in the mid 20th century, to having the downtown we enjoy today.
