I Was a Digital Nomad Who Could Live Anywhere. Here’s How I Chose My City
In June of 2021 my wife and I started actually doing what a lot of people only ever talk about. We threw all our stuff in storage, loaded up the car with our dog and all the essentials, and started traveling around North America as “digital nomads.”
She had recently started a great job at a fully remote software company. I had just secured my position at RoleCall (also a fully remote & distributed team, in case you didn’t know), and we were at the perfect point in our lives where we were established enough to fund a plan like this, but not quite so settled that it was hard to leave. We had spent the last eight years in Iowa, four in college and four as “real adults.” We had enjoyed our time and had built a great little life, but for many reasons it had become clear to us that it was time to move on.
Our nomad journey took us to Chicago for all of August, then to Toronto for the better part of three months. We spent parts of November and December in central Mexico with my wife’s family at their Bed & Breakfast, and enjoyed the holidays with my family in California. January saw us making our way up to Oregon, first to visit my extended family in the Medford area, and then on to Portland for two months.
To make a long story short, I live in Portland now. And I’m really, really happy about it.
Despite being in the business of helping people find new places to call home, I didn’t really think I would settle somewhere so quickly. One of the best things about working with RoleCall is getting to learn about so many fascinating and exciting places to live around the country, and at the start of our journey I wanted to experience as many of them as possible. I’m a terribly indecisive person, so I thought that being acutely aware of all the factors that influence relocation decisions and having so many options to consider would make it nearly impossible to fall in love with just one place. But I did!
That being said, my feelings about Portland were actually not love at first sight. It’s not really the city’s fault though. We arrived here in January, notoriously a terrible month for doing, well, anything. (Before you come for me, my birthday is in January… this does not change my feelings). It was cold, dark, and rainy, and driving in the city was next-level stressful. (I hate driving in general, but turns out I really hate driving in Portland.)
In contrast to my lackluster feelings, my wife loved it here and felt a real connection to the city immediately. Her brother lives in town, and both of them really liked being near family again. She hates the sun, so the fact that it rained all the time was a big plus for her. As a native Californian, I struggled. When she first floated the idea of staying longer, my gut reaction was “definitely not.” She had some good points though, so I tried to keep an open mind.
My first “Oh, I could live here” moment happened when I took a bus from Southeast Portland up to Nob Hill to meet a new friend for a drink. The 15 bus goes past the soccer stadium, and then up West Burnside to 23rd. As it crawls up Burnside, a main arterial street, you get closer and closer to the West Hills and their thick forests of vibrant evergreens. It’s absolutely beautiful. Then it turns up NW 23rd, which is just the cutest little commercial street and – very importantly – only a handful of blocks from all those trees. I was losing my mind at how picturesque everything was: huge trees overhanging sidewalk cafes, multi-level commercial buildings with adorably decorated window displays above and below street-level, and dozens of people walking around with ice cream cones (Salt & Straw – absolutely worth the line). On every block, I saw colorful historic homes and people sitting at sidewalk cafes enjoying Thai food and pizza and cocktails.
I mean, can you even?!
When I got off my magical bus ride to meet my friend, we took a little walk through the neighborhood.
Reader, I loved it. Like, so much it was disgusting.
We walked about five blocks down NW 23rd, and every time a new building came into view I lost my mind a little bit more. He would be in the middle of a sentence and I would interrupt with, “Oh my GOD look at that cute little Victorian house! What?! It’s a coffee shop?” I had similarly effusive reactions to the used book and crystal shop that is three houses united with one crazy paint job, the Thai place that turned a wrap-around porch into an an outdoor noodle oasis, and the majestic brick edifice that is the Legacy Medical Center.
I started looking at apartments in that neighborhood as soon as I got home. You know, just to see.
That weekend we decided to extend our stay at our Airbnb, and shortly after we started looking for apartments in earnest. It started feeling like fate when we found the perfect place, just down the street from the neighborhood I walked through and first fell in love with in the city. Now I look out my windows at those tree-covered hills every day — the same ones I admired from the bus — and think, “How is this actually my life?”
Cheers to a good decision!
Of course, trees and idyllic neighborhoods are not the only reasons people move places. There are a lot of other reasons that Portland is an ideal place for us right now.
The biggest factor is that we’ve found people who value what we value.
Portland is an incredible food city, and I love eating so much I got a tattoo of a fork on my right arm. (I also really like tattoos, and hey, so does Portland.) I’m big into sustainability, and Portland is filled with resale shops and offers municipal compost. Portland is also a very queer city, and that really speaks to me.
One of the biggest reasons we decided to make our home here was directly related to why we needed to leave Iowa. My wife is a trans woman, and the Iowa legislature is actively trying to make her life harder, with an ever-increasing focus on passing laws targeting trans people and women. She still felt safe in Iowa City, but the general political and social climate was starting to make me, as someone who loves her very much, feel nervous about how much longer that would be the case. On the flipside, Oregon has a good number of protections for LGBTQIA+ individuals, as well as laws against discrimination on the basis of gender identity. The state makes it easier to change your name or your gender marker on your identity documents, and even offers an X marker for nonbinary folks. Here, it’s easy for my wife to access the health care she needs (something that travel made unexpectedly difficult).
All that supports one simple fact: we just feel safer here.
Of course, this wouldn’t be an article about someone in love with a place if I didn’t take a moment to say, “It’s the people.” We’ve been here for six months and we already have a great group of friends, which is probably the most important factor in a newcomer feeling a sense of belonging. But even on a smaller level, people here are just friendly. Every time someone stops me to comment on my dog’s ridiculous ears, they tell me, “Have a good day!” Another sweet Portland quirk that really stuck out to me was how many people shout their thanks to the bus driver as they get off city buses.
Enjoying the cherry blossoms at Waterfront Park in the pouring rain. So Portland.
It took me a minute to warm up to Portland (and it took Portland even longer than that to warm up for me — my god it rained a lot this spring) but now it really feels like home. Every day when I open my laptop and look out my window to a beautiful view of those tree-filled hills, I think to myself, “I am so lucky that I get to live here.” My job at RoleCall made this possible for me, in many ways, and I hope our work helps people around the country feel this way about their cities too.
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