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How to Move to Your Dream City (And Actually Love It)

How we've actively created the life we want in Portland.

I'd barely spent 24 hours in Portland before I announced to Jonah, after a run that took me from downtown through Forest Park, that I wanted to live here. Every subsequent visit only confirmed our shared love of the city, with its proximity to nature and skiing, bakeries tucked into residential neighborhoods, and cozy coffee culture built around a rainy winter season. By the time we moved in October, we had exceedingly high expectations and clear visions of what our lives would look like, formed from five years of daydreams. 

Leading up to the move, I did my best to remain realistic. Ten days before I wrote, "as lovely as [this] new adventure sounds, it may also be (at best) really hard and (at worst) an enormous mistake." In the same post, I couldn't help but share some of those daydreams too, "In my idealized version of Portland, I'm jogging with my dog[...] on a muddy trail before work." 

A recent piece in the Atlantic by Arthur C. Brooks pointed out the wide chasm that can exist between expectations and reality when people move to their dream city. Moving is often so emotionally and physically taxing, it can be challenging and isolating while you get your bearings. Jonah and I had barely recovered from the financial burden of our move when we bought and moved into a house we love, but that requires a lot of time and money. But, as Brooks notes, "a large part of the unhappiness people suffer at the outset of arriving in a new place can be mitigated or avoided with a number of practices, including actively exploring your new neighborhood instead of holing up in a new home, doing the things that made you happy in your old home, and socializing with new people."

It's been nearly six months since Jonah and I pulled into Portland and, even within the limitations of the pandemic, living here exceeded our wildest expectations. But our happiness in Portland didn't find us—it came from active choices we've made to create the life we want here, like seeking out those muddy trails. For those who recently made the move to your dream city, or even relocated to a city you're hoping to love (or those who are hoping to fall back in love with your current hometown), here are a few tips I found useful in making Portland the city we dreamed it would be:

Before moving to Portland, I imagined what I wanted my weekday mornings and evenings to look like, which helped us prioritize a list of basics to jump into, while being mindful of COVID. Before we'd even fully unpacked, we started walking to new coffee shops, going for weekday hikes in Forest Park and around Mt. Tabor, adopted our dog Toast, and began creating a community here (more on that below).


Jonah and I allocated a portion of our budget to "sampling" everything in the city we're even remotely interested in so we can get to know it better, and find out what we love. I'm planning on visiting every ski resort within two hours before I buy a pass next year, we purchased a membership to the Japanese Gardens, are taking online classes from Portland Community College (Jonah's enrolled in Japanese, I'm taking ASL) and Portland Nursery on gardening, Jonah's in touch with community radio stations, we've subscribed to local publications, and attended drive-in movies for the Portland International Film Festival. (A great way to final local events is to support and subscribe to local publications—we love Willamette Week!)

Donuts from Pip's Donuts and Chai

Donuts from Pip's Donuts and Chai

Every morning, Jonah, Toast, and I go for an adventure, usually to a new trail, dog park, bakery, neighborhood, or coffee shop. Though there are definitely repeat trips (we frequent Forest Park and Dos Hermanos bakery for their pull-apart sourdough), we usually try to go somewhere new. It's such a fun way to start the day, and guarantees we've had an adventure (and tired out Toast) before we even start work.


Moving to a new city is almost always isolating and lonely—I miss my friends in L.A. every single day. But the key is to 1.) Know those emotions are temporary and 2.) Go out of your way to meet new people, because making friends in a new city doesn't always happen magically, especially during a pandemic. I'm not suggesting you do anything unsafe or take COVID any less seriously because you're in a new city, but there are still a few steps you can take to feel a bit less isolated: Ahead of moving to Portland, we barely knew a soul here so we reached out to friends of friends to let them know we were coming. When we arrived, we received so many texts from people we didn't even know yet welcoming us to the city, which made a huge difference. That first month, we filled our schedules with distanced, masked walks to get to know as many people as possible. 

If you're moving to a city where you don't have a friend of a friend, I've found that going to a dog park or anywhere where you can interact with other people can help with the isolation, until you do (and you will!) make true friends. I used many of my own tips for making friends in a new city!


Take advantage of whatever makes your city unique—even if it's entirely new to you. Since moving here, Jonah and I have learned how to snow shoe, bought bikes, will break for chicken and jojos (a delicacy we only learned about recently), and are getting slowly back into running so we can participate in Oregon's running culture and races when they come back. But your city may have a vibrant surf community (I took pre-work surf classes when we first moved to L.A.!), be really into home-brewing, river rafting, farmers' markets, or gardening. Jump in head-first! I'm looking forward to joining a sailing club, trying out futsal, and joining a roller derby club (none of which I know how to do) as soon as it's safe to do so.


Learning about a place's history can make you feel more connected to it and provide a new, important perspective for seeing it, in turn making you a more conscious and active member of your new community. Most small bookstores have some sort of "Local" section (Broadway Books and Powell's in Portland both do!). In Portland's case, I've been focused on reading about the city's racist past, something I knew little about before moving here. I'm currently reading Survival Math by Mitchell Jackson, about growing up as a Black man in Portland. 


The area surrounding Portland is nearly as vibrant as the city itself. Since moving, we've made a point of going on outdoor and camping adventures (to minimize our contact with others) on the coast and in the mountains to help orient us and explore our new state. As soon as it's safe to, I can't wait to visit wineries in Willamette Valley, drive to Seattle and Vancouver, and visit more National Parks in the area.

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