Portland, Oregon is quickly becoming a top destination for tech and remote workers and it’s easy to see why. Most often described as “pleasant,” the city offers tons of nature and greenery, great food, plenty of trendy coffee shops, and pleasant weather. Although housing costs are increasing, it’s still a relatively affordable place to live as well. As more people pursue remote work – and some get priced out of the Bay Area – tech workers and freelancers across industries are flocking to Portland. Having just spent a month there myself, I’m personally finding it difficult to say goodbye.

With that, we’re excited to introduce a new series exploring one of the best cities for freelancers each month. We’ll weigh the pros, cons, amenities, opportunities and challenges of each. And we’re kicking it off with Portland! After learning about Portland below, check out our guide to San Francisco and Oakland, CA or New York City and Brooklyn.

Freelancer livability score: 8/10

The vibe

Portland isn’t all flannel and tattoos – although there’s plenty of both. The general vibe is artsy and creative with an active edge. The sun doesn’t set until 9pm in the spring and summer, so there’s ample time to enjoy one of the city’s many hikes featuring waterfalls or views of Mt. Hood after work. Residents also like exploring the coast and camping in one of the many surrounding areas. And because so many residents don’t have traditional careers, they’re not restricted to weekends only.

Quick trip to the beach last night

A photo posted by NICK CARNERA | PDX (@nickcarnera) on


The one downside to the vibe is that you’ll often hear people talk about the negative results of the growing city. People who make higher incomes are moving in and driving housing demand, leading to higher prices in a competitive market and causing current residents with local jobs to move out of Portland proper. This occurrence is an unfortunate reality of a growing city.

However, there are positive aspects to a growing city as well. Local Peep Hannah Barrett said, “This, of course, means that your competition increases, but your core market for clients and customers grows as well. If you establish yourself as a core member of the community here, there is a great network and a huge amount of work to be had.”

Job opportunities for freelancers

Local Peep Hiedi Anspaugh said, “Connecting with the freelance and/or small business community is extra-important, but it definitely takes some digging around to find the best ways to do this. I did my own community meetups for a while with a small group of people I met through CMX and CloudPeeps.” She added, “Smaller companies here don’t want to pay very much for things like digital marketing and social media, so it’s harder to be able to support yourself 100% with freelance work. And there are no community manager-specific meetups here yet.”

Although Heidi has a valid point, it doesn’t apply to freelancers who work remotely with clients across the country or around the globe. If you haven’t already, I highly suggest creating a CloudPeeps profile and checking out the creative remote work options on the platform!

Peep and Oregon native Dusti Arab says that you won’t find many people who are serious about their careers and there aren’t many local full-time freelancers.

Hannah had a different perspective. She added, “Generally, Portland as a whole is very accepting of a non-traditional career. Everyone either has a creative side-gig or has some sort of long-term self-propelled goal. Additionally, making your own way in your field without the traditional internal ladder-style growth is prevalent. I’ve started to see an increased amount of individuals just in the last few years take their careers by the reins. Even though Portland is not yet a huge freelancing hub, I bet it will be in the next 5-10 years.”

The layout and transportation situation

Portland is essentially a bunch of really cool neighborhoods, all about a 15-minute drive or 30-minute bike ride or less away from each other. The Tri-Met bus system doesn’t have a ton of lines compared to larger cities, but it’s clean and efficient and will likely get you far enough. Uber and Lyft drivers are also ample in the city. I had a friend’s car for a few days. I have to say, it was pretty handy having the option, but you definitely don’t need one to live there.

Hannah says, “100% one of the best things about living here is the condensed, accessible city. I bike everywhere I go. Should it be excessively rainy (maybe just a few days a year), I hop on a bus or train. Between bikes and public transit, I have all of my bases covered.”

Like most cities these days, downtown isn’t the cool spot anymore. It’s where people go to work and shop (Powell’s City of Books is a must-visit). The Northeast area of Portland, specifically neighborhoods like Alberta, Missippi, Boise, and Overlook are known as the trendier arts districts. The Southeast area (Richmond, Hawthorne, Division) is also a destination for creatives with plenty of shops, restaurants, food carts, parks, and pockets of cute, craftsman-style homes.

Coworking and cafes

Heidi says that new coworking spaces popping up all the time, from small, subscription-based offices to larger organizations with resources like regular talks from experts and happy hours.

Hannah added that many listings can be found for shared desks or spaces in a less-formal way than official coworking spaces. She’s sharing space in the office of an agency where they offered her mentorship as well! She said, “Generally there is a huge culture of more than surface level networking here. It’s all about who you know, and Portland takes it to the next level. There is a strong urge and acceptance of collaborating and sharing work between people in Portland.”

Cafes and coffee shops are also plentiful, offering strong wifi and ample outlets, which is not common in every city – like SF or NY.  One of those small things that makes a huge difference.

To help you find the place that best meets your vibe, here are lists of cafes to work from:

And coworking spaces:

In addition to coworking spaces and cafes, Dusti says that places like Ace Hotel and Powell’s City of Books are also great spots with free wi-fi to work from.

Communities, events and groups

One of the benefits of a growing city compared to tech hubs that are already established, is that the events are high-quality but feel more intimate. Hannah says, “If you have a niche, I promise Portland has something for you.” Here are the events local Peeps suggested.



Life in Portlandia

Overall, Portland seems like the perfect place for a freelancer to live. Of course, it can be a challenge to make new friends when working for yourself as an adult. But, if you get out there and talk to people, it’s easier than you think. The people in Portland are very friendly and seem to genuinely care about each other. I’ve really loved my time here and could definitely see me coming back – maybe permanently! Here are some other insights our Portland Peeps had to add.

“Portland has changed a lot since I was a kid, but fundamentally, it’s incredibly livable for an up and coming city. Prices are increasing quickly, but it’s still cheap compared to other major areas with a growing tech scene.” – Dusti Arab

“Despite growing population and cost, I still find Portland to have a much stronger character, focused on the community, art, and the greater good. The plethora of galleries, venues, working spaces, and more make it a city that is never short on inspiration or someone to combine talents with.” – Hannah Barrett

You don’t have to worry about work-life balance in Portland. It just comes naturally!

“One of the best things about living in Portland is a deep respect for living your life outside of work. I like to keep my schedule pretty flexible and let my clients know when I’m taking a long weekend for a backpacking trip, because that is how the entire city functions. Most everyone not only understands, but encourages taking and enjoying time away from work and that bright glowing screen, especially since there is so much to see and do both in and out of the city.” – Hannah Barrett

Obsessed. 🏔

A photo posted by Shannon Byrne (@shannonleebyrne) on

If you’re looking for remote work so you can explore cities as awesome as Portland, check out the remote freelance jobs on the CloudPeeps platform!

*Top photo by Zack Spear.*