What I Learned by Losing an Election
My run for a local school board position reminded me how difficult it is to turn complicated ideas into one simple message — even for those of us who do that for a living. Here are the lessons my campaign taught me about clarifying your message.
Millions of people were anxious on Election Day, but I was more anxious than most. Like everyone, I was waiting to see what would happen at the top of the ballot. But I was also watching the very bottom of the ballot, where my name appeared as a candidate for Oakland School Board.
With watch parties nixed by the pandemic, I settled into the couch with some pizza and a bottle of wine. I’d spent the last 12 hours standing outside of a local precinct, trying to persuade last-minute voters. The polls closed. States turned red or blue on the TV. Pundits made predictions as results trickled in. And I sat there nervously refreshing the Alameda County registrar’s page on my phone, hoping to see some good news.
The past five months collapsed into a few hours, as I replayed key moments from the campaign — fundraisers, candidate forums, virtual town halls, canvassing days, and conversations with voters. The words of supporters and detractors circled in my head. My confidence ebbed and flowed.
When the first vote tally finally appeared, I felt a mix of disappointment and confusion. I was in second place with only a small portion of the votes counted. I went to bed late, like all of us, with no answers. The Presidential race was far from over. My own race was unclear. My mind was racing, but the exhaustion of the campaign sent me straight to sleep.
In the days that followed, it became clear that the initial votes were an accurate predictor of the final outcome.
I’d lost the election.
Getting my story straight
Running for office is unlike anything I’ve ever done before. It’s the ultimate emotional rollercoaster. Some days you win an important endorsement, receive a generous donation or talk to a dozen voters who decide to support you; other days you’re publicly disparaged, you’re out-maneuvered, or you stumble in an important candidate forum. A campaign requires so many skills — strategy, organizing, fundraising — many of which are totally new.
The one challenge I didn’t expect was communications. I’ve spent years helping people and organizations shape their story and share it with the world. I assumed this part would come naturally, that I would quickly develop a good slogan, a stump speech, and campaign literature that would resonate with voters.
It wasn’t that easy.
Political consultants and expert storytellers will tell you that you need a simple, memorable idea to associate yourself with. When people hear your name or see a yard sign, they should think “Oh! That’s the ________ candidate.” From “Compassionate Conservatism” to “Change We Can Believe In,” successful campaign slogans are drastic oversimplifications of dozens of specific policy proposals. But that’s the point. They invite people into a story and offer them a role to play in what lies ahead. As former New York governor Mario Cuomo famously noted, “politicians campaign in poetry, but they govern in prose.”
My campaign struggled to find a core message at times. It’s difficult to distill years of experience and complex ideas into a few words. To be clear, I didn’t lose because I lacked a catchy tagline. But as a relative newcomer, I needed all the help I could get to stick in the minds of voters. Looking back, I can identify a few moments in the campaign that served as reminders of the basic principles that I’ve used to help others tell their own stories.
Ask Others
Creating a brand or developing your own story is difficult precisely because you’re too close to it. You know too much. You care about the nuance and the details which, while important, are too difficult to quickly communicate. That’s why people hire consultants — not just for their experience, but to hold up a mirror and help them avoid well-worn narratives that make it hard to connect with an audience.
Oakland is deeply divided when it comes to education. In recent years, the anger and frustration of people who believe in different paths forward has reached a fever pitch. Fights have broken out at board meetings and people have protested outside of the superintendent’s home. This growing divide was something the new board was going to need to address. A friend of mine reminded me that although I grew up in a conservative Texas town, I’d adopted more progressive politics over the years, and I’ve always been able to connect with the people who shaped my early life. Though we often disagree, I love having conversations across lines of political difference about the things we have in common and the ways that we might see one another as more than two-dimensional political caricatures.
After that conversation, I focused the early part of my campaign on mending the divides in our city. Inspired by a friend’s campaign in Minnesota, we told voters that “A Better OUSD Starts With Us,” inviting the adults to have a better conversation about how to create a better future for students. At other times, we implored people to focus on “Progress, Not Politics.” And playing off of the formal name of the district — Oakland Unified School District — we cast a vision of “One Oakland, Unified” and focused the messaging on coming together for the common purpose of improving education for students in our city.
Get Emotional
Sometimes, strong emotion can be clarifying. Whether it’s anger or joy, awe or disbelief, feelings can override our tendency to overanalyze. When your goal is to create an emotional connection, feelings can often point you in the right direction.
One of the most emotional moments of the campaign came during an interview with a local weekly paper weighing potential endorsements. The candidates were asked what indicators we would look at to determine if the district was moving in the right direction. I was shocked when I was the only candidate who said “academic achievement.” Others pointed to parent sentiment, teacher turnover, or student joy — all important things, but not, in my view, the most important indicator of success. Having worked in education for more than a decade, I knew the divides around measuring student learning and that certain phrases were heard as code for “high-stakes testing.”
But I couldn’t help thinking of the third graders in my class years ago, many of whom started the year well below grade level in both math and reading. If I hadn’t been focused on their academic growth, I wouldn’t have had the “whatever it takes” mindset needed to help them close the gap. The thought of making anything but academics our primary goal flew in the face of everything I believed. Yes, I want teachers to love their work and parents to be engaged and students to experience joy — but those things are in service of helping students learn. My frustration inspired a message of radical focus that appeared on our posters: “Every student. Every decision. Every single day.”
Look to Your Past
Unfortunately, my moment of clarity came in the last week of the campaign, with too little time to reshape my message for voters.
A key theme of the campaign was literacy. Oakland schools are in crisis: Just one in five Black students and less than one in three Latinx students is reading on grade level, which is well below their White peers. Literacy is the foundation of a good education, so much so that many consider third-grade reading ability the best predictor of long-term academic success.
So, of course, this message became a central part of my platform. Literacy instruction had been a passion of mine since my time as a teacher. When I left the classroom, I piloted a literacy nonprofit called We, The Readers and I’ve taught developmental English with the Prison University Project at San Quentin for the last five years. It was a topic I cared about and knew a lot about — and the stark reality of the situation in Oakland made an emotional connection with voters.
I was working on the campaign’s final push when I got a text message from my sister-in-law. She’d found one of my old business cards from We, The Readers which featured the tagline: “Literacy and justice for all.” It was perfect. Yes, it was an oversimplification of my campaign agenda, but it was simple in the best way. It channeled the focus on student success in terms of the most pressing issue, and it spoke to equity — all in just five words. It was an Aha! moment that came a little too late.
In the end, I’m proud of the smart, student-centered, positive campaign we ran. It wasn’t always easy. After all the unflattering articles, the angry members of the public, and the stolen yard signs, I have enormous respect for every candidate who’s been elected to office. And while I struggled to find the one central theme that would animate my campaign from start to finish, I learned a lot about where to look for a good message.
Which should prove useful if I ever do this again.
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