Twenty Years in Portland

SolTerra Building, SE Division St, 1 March 2021. Agfa Isolette/Kodak Ektar 100

April 4, 2001, I’m dropped off in Portland via Amtrak’s Empire Builder. After almost a quarter-century in Connecticut and an unsuccessful year in the Bay Area, I was ready to give Portland a go. I didn’t know that much about The Rose City, I just knew that it was an attractive and affordable city, one where there was a good alternative arts culture. I had a few friends here, so I wouldn’t be completely lonely. I didn’t know how things would work out and how long I’d be in town, but I was willing to make a go of it. Within a month or so, my friend Chris and I found a cheap place to live on SE Morrison St and I found a “it’ll get me by, for now,” job at a Postal Annex off of NW 23rd. It was a start.

Twenty years later, through thick and thin, I am still here in Portland. I’ve entertained a few notions of leaving over the years, but here I stay. And I think I’m going to stay here as long as possible, or until I “retire”, whatever that means. That’s because I love this place. Right now, there’s no other place I’d want to live.

Oh yes, I realize that Portland’s star has lost its luster, especially over the past year. Yes, there have been protests and a spate of unrest, but never as bad as the national media makes it out to be. There is a housing and homeless crisis. But Portland is not “over”, nor is it a dying city. I don’t really care if Portland gets trashed on the national/international stage. And it’s okay if people don’t want to move here in the numbers that they used to. There are other places to live. But I choose to stay in this one, for as long as I can.

I’ve made roots here in Portland. I’ve learned a lot about the city over the past two decades. I’ve tried to be as much of an “active participant” in the city as possible. I haven’t run for office, but I have worked at non-profit organizations, volunteered for boards. I lead bicycle and walking adventures that explore the city. I enjoy showing folks the hidden and interesting in this town. I edited a guidebook to the city that’s been a best seller at Powell’s Books. I’ve been featured in some form in all of the major newspapers, in Portland Monthly magazine, even on the radio and television. This doesn’t mean I get the “good seat” at restaurants (when they’re open), but I do feel some degree of pride in all of this.

And it’s really nice to find A Place I Want To Be. This is very important. Because while Connecticut had a big part of making Who I Am Now, I never felt comfortable there, never felt like I belong. I know many people live in the same place their whole lives and never move from where they grew up. Some people do this because it’s expected, or they don’t know what else to do, or they’re afraid of change, or some combination of the above. I admire those folks who truly like the place they grew up in and are happy staying put. I knew that it wasn’t going to be the case for me. I had been growing anxious and weary of life in Connecticut, and approaching my quarter-century on the planet I knew something had to give. I had to at least take a chance on life outside, or resign to the fact of being a permanent Nutmeg State denizen. I finally worked up the courage to leave in the summer of 2000. And I haven’t looked back.

That’s because Portland has been the opposite of Connecticut. The Constitution State did its best to repel me, the Rose City its best to attract me. From Day One I’ve felt like I belonged here. Portland just suits me. I like its geography, climate, and location in the world. I love the culture that’s developed over the years.

As I grow older, I feel less of a desire to pull up roots and move somewhere else. Getting out in the scene and being open to meeting a lot of different people in a short span of time is easy in your twenties and early thirties. Mid-forties? Not so much. I know if I had to move, I could. But there’s something to be said about the comfort of living in a place that you like for a long period of time.

Still, twenty years! I really didn’t expect that I’d be here this long. When I moved here in 2001, I was 25 going on 26. I had spent all but two years of my life in Connecticut.* I was obviously itching for a change and ready to take on the world. I thought I might spend a few years in Portland, and then maybe end up somewhere else, maybe Chicago. (I liked Chicago a bit back then.) I arrived in Portland with an open mind and lots of enthusiasm. Portland was not as well known to those outside of it back then, so I had little in the way of expectations. That was good, as I let things happen organically. I think it may be harder for folks who move here now and have a preconceived notion of what Portland is. Anyways, I thought I’d stick around until I got bored, or felt like moving on. Twenty years later I’m still here.

My life before Portland feels so distant now, yet moments from my early days here don’t. For example, I was thinking about the place I lived at off of North Vancouver and Fremont, wondering what those roommates are up to. The memories of that place still feel fresh, yet it’s been about seventeen years since I lived there! While sometimes the past twenty years in Portland seem like one big blur, when I sit down to analyze it I can break My Portland Life into distinct segments:

  • The early days/golden era: 2001-4. Of course, the first days in a place you love turns into Golden Years. This was when I mostly lived in my SE Morrison apartment. I threw myself into the scene, volunteering with the IPRC, working on the Portland Zine Symposium, getting to know the people and the place. Everything was on the up and up.
  • Confusion zone: 2004-6. A couple years of questioning myself, being really poor, and moving around a lot. Not a lot of positives of this era, but I did start the Urban Adventure League then and also started bike touring.
  • Silver Age: 2006-10. I started my job at the hostel and found more stability in my work and home life. The bike scene was off the hook and I threw myself in it. I made a lot of friends and found love after a long drought. And I really got into bike touring.
  • First Co-Hab: 2010-13. I moved in with my girlfriend April. We went on the Big Tour across the Continent in 2011. I get really bike geeky. I start Society of Three Speeds. There was a good deal of superlatives, yes. But the slow moving implosion of our relationship post Big Tour dominated the last couple of years.
  • Dark Days: 2013-17. Out of love and working a job I didn’t care for anymore. I lived in a house in Woodlawn which I thought was a good idea at the time but it slowly turned toxic. I continued doing the things I had been doing before, but I was pretty depressed and doubting myself. I was pretty lonely too, despite one brief fling. Positives of this era are traveling to the Midwest for Lake Pepin Three Speed Tour.
  • Rebuilding: 2017-present. I found love again! Emee has helped me rebuild confidence in myself. I finally extricate myself from toxic situations (Woodlawn house, the job at the hostel) and work on my own projects instead.

And what does the future bring? What will be my next era? I don’t know, but I hope it’s good.

To close this out, I’m excerpting a blog post I wrote in 2011, after I got back from the Big Tour. Ten years on, it still encapsulates my feelings for Portland pretty well:

I looked at my cyclometer. I had barely pedaled 7 miles from my house in inner SE, a neighborhood about 3 miles from downtown. 10 miles from downtown Portland, a city pushing 600,000, and (I’m passing by) a sheep farm. For comparison, when we visited Chicago last month, we stayed in the Rogers Park neighborhood, about 10 miles from downtown. Rogers Park is on the edge of Chicago and is still a thoroughly urban neighborhood. Powell Butte is on the edge of Portland, but still within city limits. There were no sheep farms in Rogers Park.

And this is one reason why after traveling around the U.S. and Canada quite extensively over the past decade, I still return to Portland. No, it’s not about the sheep farm per se, but what the sheep farm means. Portland is as urban as I want it to be with all the bells and whistles. But it is so close to rural areas and actual wilderness. An hour of biking brought me to a sheep farm on the side of an extinct volcano, with a view of a dormant volcano in the distance. Another hour and a half of riding would bring me to that view of the Columbia Gorge shown above. Ride all day and I would reach the base of that dormant volcano in the distance.

I needed to see these things. I’ve been back in town for nearly two weeks, gotten reacquainted with old friends and stuff that I do that is within the urban core. But it still feels so weird. Am I really back? Why am I back? Sometimes I feel like my extended trips are an opportunity to find another town to live in. Well, it’s not like I’m actively looking for to move, but maybe more so a taste test of new flavors. Can I live in this town? Many places I can imagine living in for a short time, tolerating it for a year or two if circumstances dictated. A few towns I could see being happy in for an indefinite period of time, like Vancouver (BC) and Minneapolis. But could I leave Portland? Rides like this remind me why I live in the Rose City. Yeah, I had to ride through some dumpy areas (and will ride through some more), but every town has its dumpy side. The positives are what matter. And positives like the view of Mount Hood that greets me on the trail around this point.

*Besides my 2000-1 stint in The Bay Area, I spent 1990-91 in North Carolina.

2 thoughts on “Twenty Years in Portland

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  1. Nice retrospective. I’m really happy things are working out for you again in Portland, and that you continue to stay and make a living. Moving all the time and feeling unsettled is a crappy feeling, made worse by job and other uncertainties. I like how you’ve put your years into “chapters”. It’s great that you’ve found the city for you, and done your best to make yourself a part of it.
    I’m still not sure where I’ll end up living in one year or five years from now. Haven’t had the feeling of “home” in a long time. If I could, I’d live in Portland too.

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