Photo-Illustration: The Cut; Photos: Getty
A few months before I accidentally embarked on a brief and unlikely career in electoral politics, I was wallpapering the dingy hallway where my cat’s litter box lives. When I bought the wallpaper, greenish-blue and printed with owls, I had been feeling the kind of soul-badness that approaches physical pain. I had a book come out in August, which led to a postpartum slump, and since then, October 7 had happened and Palestinians were being crushed under rubble with U.S.-made bombs and acquaintances from college were trying to argue with me about the 1947 U.N. Partition Plan via Instagram DM. Every day, I called Oregon senator Ron Wyden’s office to demand that we stop supplying bombs to the Israeli government. Every day, the same young staffer would assure me with maddening serene courtesy that he would pass along my concerns to the senator’s foreign-policy team.
I had broken a streak of absenteeism at my local chapter of the Democratic Socialists of America to attend BDS working group meetings. I had gone to the Portland Book Festival with a corny homemade cease-fire pin. But Wyden, and most of his peers in the Democratic Party, maintained an obdurate silence. My disgust metastasized, and I receded into the hypnotic work of lining up the owls around our ancient pipes and electric meter. Eventually the hallway was done, and I went on Wellbutrin.
While I had been disassociating with the owls, Portland had been gearing up for a historic change to its municipal government (this sounds boring and opaque, which is how they try to keep people from paying attention to things). In 2022, Portland voters approved a transition from our janky commission form of government — four commissioners tasked with running all the city’s bureaus — to a system with 12 councilmembers from four districts. The new system would use ranked-choice voting, which had shown to yield more diverse, more representative governing bodies in other places. The hope was that Portland would end up with a group of leaders who looked more like the city they were leading, and who could craft policy and leave the administration of city bureaus to professionals. This change meant that for the first new election of 2024, the field was wide open. Over a hundred people threw their hats in the ring, including my neighbor Tiffany, a third-grade teacher at a local public school.
Tiffany is a mom of two, like me, and our kids were friends from the block. Even before I watched her help local kids start marches for Black Lives, gather more than 1,000 signatures to get universal preschool on the ballot, and organize with fellow teachers to lay the groundwork for a historic teachers’ strike, she was a figure of awe to me because she was a truly great neighbor and uncannily good with kids. She was that person you dream of when you dream about the village in which we are supposed to raise children; someone who squats down to talk to them with the kind of intense and unpatronizing interest that cannot be feigned and which she also directs toward adults. She was the antithesis of what was disgusting to me about politics, the kind of person who not only really cared about people, but who felt the urge to do something. When she told me she was thinking about running, I told her, genuinely but also naïvely, that I wanted to help.
Other volunteers lined up, few of whom knew anything about campaigns but knew a lot about other things. Someone made a website, someone made logos, someone made a communications plan, someone made social-media slides, someone set up the finances. I started handling her inbox and giving her rides to events, smoothing down her flyaways before she got her photo taken. The first big fundraising task was to hire an experienced campaign manager, but it turned out that there aren’t actually that many of those who are available and affordable to a first-time City Council candidate. And I was there, and underemployed, so Tiffany said, “Why don’t you just be the campaign manager, and I’ll pay you?” Like all good teachers, she knew how to get people to rise to an occasion. Like a union worker, she believed in a decent wage.
“This is not really me,” I told myself when I panicked about how big a job we had both taken on. “We’re in this for the right reasons,” unlike the self-serving perverts who have always aspired to politics. But to be a politician or someone whose job it is to get them elected, you can’t just aw-shucks your way through it. You have to work hard, and you have to have some hard streak in you that really wants to win.
As a writer, I was familiar with an embarrassing, mostly subterranean hunger. In my normal life, I needed this primordial desire to muster the discipline required to finish a book. On top of this, a decade of admin jobs had trained me in a tradition of striving, conscientious tight-assery that I had subsequently deployed in my writing life to chase down invoices or write obsequious emails to editors or file the Schedule C. This training was even more useful now: I had to make a budget and learn the arcane secrets of the Voter File and write emails that said one thing and meant another. Like being a writer and an administrative assistant, being a campaign manager is undignified. You have to sometimes eat shit and do things you don’t want to do. You have to flail and ask for help. But you also get to tell a story to every single person whose door you knock or phone you call and hear their story in return. There’s an element of performance coupled with a real opportunity for human connection that was deeply interesting to me.
And Tiffany was killing it, and she had a great story to tell. She raised more money than anyone else in the city by a mile, all in small donations. Around 200 people of all ages and from all walks of life were inspired to volunteer their time in some way. She got endorsements and support from a ton of labor and community organizations, including the DSA chapter, which made me happy because it was my political home. There was a compelling David and Goliath angle: Everything about the election was set up as though candidates did not have day jobs or kids or both, and Tiffany still had to support her family, teach her class, and be there for her children. She was powering through very long days, and the local Establishment kept her at arm’s length. One newspaper explicitly withheld its endorsement because she had helped organize the teachers’ strike; another declined to interview her at all.
Depending on the day, it was either destabilizing or freeing to realize that many political campaigns are made up of people who don’t know what they are doing, and that some of the people who act like they can tell the future have no idea. I thrived under the constant fire-drill vibe even as I felt it eroding my physical and mental health. I started smoking again in earnest, believing (incorrectly) that my husband did not know. I watched Veep to “relax” and slotted myself into its hideous archetypes. Now I was Gary; now I was Amy; now I was Sue and Dan and Mike. Tiffany and I would joke about this. “Ma’am, continuing to love the hair,” I told her when she got a haircut.
Like Veep, any exposure to real politics reminds you that they are bad. We swiftly learned from people with experience that a crucial aspect of running for office involves making a list of everyone you know, and everyone they know, and then calling them on the phone to ask for money. Then your campaign will take that money and spend it on fucking Instagram ads and pieces of mail that cost obscene amounts (easily $15,000 for a batch), many of which will get tracked into vestibules on a muddy shoe. But the scarier part is what happens next. Tiffany’s whole thing was that she was a political outsider (itself a well-worn trope) who would now go and change things on the inside. But inside is where Ron Wyden and all the other allegedly progressive politicians were, too.
Tiffany and I knew that electoral politics would not bring about liberation, but we also knew that divesting from them entirely cedes power to the people who slash public programs to save on their tax bills, who propose jails instead of housing, who enthusiastically press the “yes” button on genocide. Sometimes we would go back and forth: Should she go to this meeting? Should she sign this letter? We would sit in the parked car outside one of our houses, processing, arguing, and spiraling while our kids were asleep inside, another bedtime missed. I could not have done this with anyone other than a friend, because we had to be able to be vulnerable and trust each other in a way I have never experienced, or expected, at any other job.
Finally, in November, Tiffany won. She became the first Asian American woman ever elected to Portland’s city government. A mom and third-grade teacher and rank-and-file union member and friend and neighbor had won a seat in this new form of government. On a world-historically horrible Election Day, the results in Portland surpassed my wildest expectations. I felt disbelief, and joy, and relief, and just the slightest twinge of loss as I realized this brief, intense thing we had all made together was coming to an end. And I felt so proud of this person who had always believed she could do this and who brought us along too.
At the start of 2025, I went to the first City Council meeting and watched our new 12-person council around the dais. It was, by every measure, a totally different city government. There were more people of color and queer people than in any other city commission, cumulatively, in Portland’s history. There were working-class people who worried about when their health insurance would kick in. There were three Democratic Socialists and six people who had made some gesture toward Palestine. The room was packed, full of media and lobbyists and gawkers and comrades in the balcony holding protest signs. Soon, there was the type of cataclysmic A/V issue that could only happen on the first day of a new form of government. There was heckling, and a back-and-forth about decorum, and a nine-round voting deadlock to figure out who the City Council president would be. In short, there was mess, the kind of mess that accompanies any collective human effort. As I watched the councillors speak and perform and maneuver in ways I had learned to read and interpret over the last year, I felt some foxlike creature inside me stir and prick up its ears with interest. I noticed it, patted it fondly, sent it back to sleep, and went home to my owls.
