Dear Portland, we still love you

Advertiser Disclosure: rich & REGULAR is a member of affiliate marketing programs and may receive commission in exchange for promoting products and services.

Our relationship with Portland, OR (PDX) is complicated. It’s one of a few places we’ve visited several times that has always left us wanting more. But we’re also students of history and unlike many of our well-intended friends and allies, we see color.

We see the picturesque snow-capped mountains, lush green treelines, beautiful bridges and blue coastlines of the Pacific Northwest. We see the gorgeous, golden tones of a seemingly endless supply of local brewed beer. And we see white people; lots and lots of white people. After all, it is Oregon where only 2.2% of the population is black.

Portland is also well known for their food scene and having enjoyed it on several occassions, we’d put PDX up there against any other city we’ve visited in the world. In fact, we’ve had more memorable meals in Portland than anywhere else we’ve visited in the past ten years. By our estimation, the artistry happening in Portland kitchens is seven years ahead of the mainstream so when we visit, we gorge ourselves like grizzly bears before hibernation. It’s like eating and drinking the future bro.

Unless you’re in the foodservice industry, an artist or actively looking to find a thriving community for the weirdest corner of your personality, there are plenty of reasons to not choose Portland as your next vacation destination. I suppose Portlanders would prefer to keep it that way but if you’re curious, here are a handful of memorable moments from our trips to Portland over the years.

Creativity is in the DNA of the city, so you can see Portland’s corky personality on full display in home design, cars, bikes, gardens and fashion on any given day. That unique spirit is exactly what Fred Armisen and Carrie Brownstein tapped into when they made Portlandia and it plays a supporting role in Hulu’s brilliant new comedy, Shrill.

If you let it, Portland is one of those places that can inspire you endlessly because the people there encourage free-thinking and open dialogue. One of the ways they do this is through the Naked Bike Ride. So we’re clear, the Portland Naked Bike Ride is EXACTLY what it sounds like; a bunch of people deciding to ride bikes together through the streets of Portland…butt a$$ naked.

We had no idea this was a thing or that it was happening until a few hours before it started. This isn’t just the ultimate expression of freedom, it’s a community gathering to encourage the use of eco-friendly transportation [like bicycling], body diversity and support free thinking. Here are a few blurry pics from our cutting room floor as we watched FROM THE SIDELINES with our clothes on.


At the expense of our fairer skinned brothers and sisters, we could make a number of jokes about the cool weather that night or ask hygiene related questions about bike seats. But we’re all grown ups here and we truly do respect the purpose of this gathering. So let’s just transition to the part of this article about food without making some immature food cliche reference.


Portland’s food scene


With every meal, there’s a steady supply of beer on hand since Portland has more breweries than any other city in the US. But, if beer isn’t your thing, the Oregon wine country and Williamette Valley is just a short car ride away where world class Pinot Noir and other wines are made. Some of our faves include Big Fire, A to Z and some wines we discovered recently by Andre Mack, a rising star in the wine world and card carrying member of Wakanda.

At least three times a year we sit in a pool of drool reminiscing about the amazing meals we’ve had in Portland. From quick breakfasts at diners, to sandwiches, food trucks, cocktail hours and epic brunches, the city has left us with an amazing list of food memories.

Here are just a few of our highlights over the years.

Portland is also the only place in the world where we actually waited in a long line outside a restaurant hoping to get a seat. In case you’re wondering, it was for brunch at Tasty and Alder and it was worth every single minute. There are no pictures of this meal because honestly…

it was a spiritual experience that needeth not be sullied by the presenth of thou iPhone

Gastronomy 50:11

One of the reasons Portland’s food scene is so amazing is because they believe deeply in sourcing products locally and supporting the local ecosystem. So well before, “farm to table” dining became a a thing around the country, it was just how they did it there. Along those lines, you won’t find many chain restaurants in the city. Instead, you’ll find locally owned and operated businesses that source as many products as possible from nearby purveyors. From our point of view, Portland’s ability to balance both it’s community’s values with business goals is admirable and worthy of replicating in other pockets of the US.

Filming Playing with FIRE

In 2018, we were all set to go to Austin, TX for a PDX inspired foodie weekend getaway. At the time, we were in talks with the film production team to meet while we were there but those plans fell through and we re-organized the trip to visit Portland instead. While there, we got to know Travis [the Director], tell our story and share our perspective on the FIRE movement.

Filming Playing with fire, upcoming documentary

We were on such a high that after the shoot, we went out for drinks at a nearby restaurant. Low and behold, while we were there, a political riot broke out on the street we were on. There were police barracades, tanks, protesters and unfortunately a few people were also injured. We didn’t know exactly who was who since they all just seemed to be on edge.

As the crowd got tense, the restaurant manager simply closed the garage door opening to the restaurant and the DJ ominously spun Childish Gambino’s, This is America, on repeat.

It was a moment we'll never forget, a shit stain on a pretty summer day and a blemish on an otherwise romantic tryst we've enjoyed with the city. Click To Tweet

Events like this, the recent incident on the PDX train and a handful of others are also a humble reminder of Portland’s racist history and why despite having built some great relationships with people there, we could likely never call it home. We know a black community exists there, but it’s really small, shrinking and actively being pushed out due to gentrification.

Would we visit Portland again after this? Absolutely!

We know exactly what it’s like to have a few bad apples get in the way of your best efforts to make progress. We wouldn’t judge an entire community simply because there are laws in place that allow people to have a voice.

In that same vein, due to our corporate careers and social backgrounds, we acknowledge being more comfortable navigating [white] spaces that might make some people of color uncomfortable. We don’t always enjoy being the only people of color in the room but we’re certainly used to it. With that said, in a way…

cities like Portland, and the FIRE community have a lot in common. Click To Tweet

Though there have been some questionable moments, we’re not suggesting that the FIRE community has a racist legacy. But we do acknowledge that many of the faces of the movement are white. Also, many of the FIRE success stories and blueprints to follow are told from a white American experience. Like anything else, this sends signals to the broader community of how inclusive a space it may be and has a tendency to undermine the intent of the lesson.

We get this and it’s why we knew we couldn’t tell our story anonymously if we genuinely wanted to inspire more people of color to get on the FIRE train. It’s also one of the reason’s we willingly stand at the intersection of personal finance and diversity despite the constant awkward pressure to speak on behalf of 35 million people.

It took a few years, but when we went to Thailand, Peru and honeymooned in South Africa, we inspired others to consider them as travel destinations. When we got married in New Orleans, we inspired our family to travel, let loose and create lifelong memories. If we’re lucky, and with the help of films like Playing with FIRE, we believe we can be trail blazers for cities like Portland and the FIRE movement too.

See what we did there?

5 comments

  1. I’ve only been to Portland for one day on two separate occasions, but it was definitely a great city with a lot of quirk. But yes, it’s also incredibly white, so I can see where that could be a problem for people of color. Or really, a problem in general because diversity is obviously important. Still, it’s a great town and I’m glad you had such great experiences there!

  2. Thank you for this post. I live in and love Portland for the reasons you mentioned – creative, great food/beer/wine scene, weirdness, etc, but I can’t stand how white and male-centric it is. I moved here 20 years ago from San Diego. The first thing I said when I moved here was “Why are there so many white people here?” It is very strange and disorienting when you’ve grown up in a more diverse place.

    And, you are exactly correct, especially with racism being acceptable at the national level, racism exists and is being allowed to overflow here in Portland – from Portland itself and from the outside (for example, Proud Boys from Washington are allowed to rally here although they aren’t residents). It is heartbreaking and infuriating. While our community leaders are well-intentioned (and mostly male and white until our May 2019 election), they don’t understand the complexity of the issues (or choose to ignore it) creating greater issues. They are afraid to address problems head-on which creates more resentment and mistrust. I am finding it more frustrating and demoralizing to live here.

    All of that said, we have some wonderful, hard-working organizations such as Center for Diversity and the Environment and Center for Equity and Inclusion (there are others, of course) trying to dismantle racism in Portland so that we may, together, build a more just and equitable community so that all of us thrive. I hope that will happen by the time my son and his classmates grow up and take over the leadership of this city. I don’t want to leave them them this legacy of systemic racism.

    I really appreciate your post and your kindness toward our fair city. Thank you!

    • Thank you so much for sharing details re: the organization you work for. We’re still learning about Portland and still love visiting there. We’ve even discussed spending extended periods of time in the city but after the last visit, we’re giving it a little more thought. It’s good to know the residents have put leaders in place who have a greater understanding of the issue.

Leave a Reply