As I stood on the National Mall the week of Obama’s inauguration, there was a sense of finality to the celebration. It felt as if we were witnessing the last chapter of a decades-long struggle and the birth of a new progressive era.
Congressman John Lewis—whose skull had been fractured leading the march for voting rights across Edmund Pettis Bridge forty-four years earlier—declared, “Barack Obama is what comes at the end of that bridge in Selma.” Some conservatives said that Obama’s ascent was proof America had entered a “post-racial” period. Democrats were on their way to a sixty-seat majority in the Senate, and there was speculation the Republican Party could be on the verge of elimination. Bill Clinton’s former campaign strategist even published a book predicting Democrats would rule for the next four decades.
In the months and years that followed, I ran into campaign alumni at miniature reunions during GOTV or on the sidelines of Obama’s second inauguration and heard about the paths they took after 2008.
Meghan Goldenstein finished the master’s degree she put on hold to join the 2008 campaign and ended up working at a Chicago nonprofit that teaches civic engagement to middle and high schoolers. Every four years since, she takes a new group to Iowa so they can witness the caucus process that had such an impact on her.
Stephanie Speirs became an entrepreneur. She started a Boston-based company that brings solar energy to low-income communities and says that her experiences as an organizer and a waitress are the two she draws on most in her current daily life as a CEO.
A few former organizers ended up back in Chicago, working for the United Way. Others went to law school. Or business school. Or divinity school. Some moved to San Francisco and worked for start-ups. Others became teachers and social workers. Several, like Megan Simpson, Michael Halle, and Ally Coll, dove back into campaigns and hopscotched across the country for years.
Still others, like Yohannes Abraham, came to the White House and helped pass legislation that expanded health care insurance to twenty million Americans, reformed Wall Street, and confirmed two Supreme Court justices. Appointees at federal agencies, former organizers like Esther Morales, implemented presidential initiatives that cut carbon emissions and supported clean energy. Hundreds more worked across the federal government to expand LGBTQ protections, spearhead criminal justice reform programs, reduce student loan debt, and prevent another recession.
The experience even led some to became media stars. Jon Favreau, Tommy Vietor, Dan Pfeiffer, and Alyssa Mastromonaco started podcasts or wrote books that offered platforms to shine spotlights on candidates and direct money to progressive causes.
Like most alumni, I hoped Obama’s record and strong approval rating would help carry another Democrat into the White House to continue his work. And so, eight years after Obama’s inauguration, in the lead-up to the 2016 election, I returned to North Carolina to volunteer for Hillary Clinton. Walking into a local volunteer office to get my packet, I could scarcely contain my impulse to scream at the field organizer training me, “I used to have your job!”
In North Carolina, I visited former volunteers who were still leading canvasses and organizing rides to the polls. For so many who volunteered for the first time in 2008, Obama’s margin of victory had rewarded what little faith they had in politics. His success was proof that despite obstacles, fundamentally, the American system worked, and it was possible to accomplish something that had never been done before.
The election of Donald Trump, a reality television star whose political ascent in the Republican Party was sparked by his “investigation” of Barack Obama’s citizenship, did serious damage to that faith. That he would win the electoral college with nearly three million fewer votes than Hillary Clinton only further laid bare the structural shortcomings of our democracy and all that remained undone despite the past eight years. In the weeks following Trump’s election, I heard people talk of little else.
“Why didn’t we focus more on state legislatures?”
“We need to plan an event that trains people how to run for office.”
“How can we get volunteers in safe districts connected to flippable seats?”
This feeling of existential dread extended far beyond former organizers. A friend’s uncle in Queens told me he was so shaken by Trump’s election that he planned to dedicate all his free time and disposable income to taking back the House of Representatives in 2018. “That will not happen,” I thought. “Gerrymandering makes it impossible.”
Ten days before Obama left office, my wife, Fiona, another ’08 organizer, and I flew to Chicago for the president’s farewell address. The night was supposed to be a break—a nostalgic interlude in the face of looming disaster. But waiting for Obama to take the stage, I wondered whether his farewell would sound more like an elegy, as the accomplishments we gathered to celebrate were in danger of being washed away.
The speech began with Obama reciting the origin story I had heard so many times in Iowa: a directionless young man, looking to make a difference, who came to Chicago and found a purpose in organizing. He listed the greatest hits of his administration: passage of the Affordable Care Act, the Iran nuclear deal, marriage equality. But his words focused less on the past and more on the potential to meet the challenges ahead.
BARACK OBAMA [Speech Excerpt]: But that potential will be realized only if our democracy works… our democracy is threatened whenever we take it for granted.… It needs you. Not just when there’s an election, not just when your own narrow interest is at stake, but over the full span of a lifetime.
If you’re tired of arguing with strangers on the internet, try to talk with one in real life. If something needs fixing, lace up your shoes and do some organizing. If you’re disappointed by your elected officials, grab a clipboard, get some signatures, and run for office yourself. Show up. Dive in. Persevere. Sometimes you’ll win. Sometimes you’ll lose. Presuming a reservoir of goodness in others can be a risk, and there will be times when the process disappoints you. But for those of us fortunate enough to have been a part of this work, to see it up close, let me tell you, it can energize and inspire… that faith I placed all those years ago, not far from here, in the power of ordinary Americans to bring about change—that faith has been rewarded in ways I couldn’t possibly have imagined. I hope yours has, too.
Some of you here tonight or watching at home were there with us in 2004, in 2008, in 2012—and maybe you still can’t believe we pulled this whole thing off… to all of you out there—every organizer who moved to an unfamiliar town and kind family who welcomed them in, every volunteer who knocked on doors, every young person who cast a ballot for the first time, every American who lived and breathed the hard work of change—you are the best supporters and organizers anyone could hope for, and I will forever be grateful. Because, yes, you changed the world.
That’s why I leave this stage tonight even more optimistic about this country than I was when we started. Because I know our work has not only helped so many Americans; it has inspired so many Americans—especially so many young people out there—to believe you can make a difference; to hitch your wagon to something bigger than yourselves. This generation coming up—unselfish, altruistic, creative, patriotic—I’ve seen you in every corner of the country. You believe in a fair, just, inclusive America; you know that constant change has been America’s hallmark, something not to fear but to embrace, and you are willing to carry this hard work of democracy forward. You’ll soon outnumber any of us, and I believe as a result that the future is in good hands.
Listening to the speech, surrounded by other alumni, I thought back to Obama’s first campaign. Back then—when you sat alone at your computer to donate five dollars, or approached a stranger in a gas station parking lot to ask about voter registration, or knocked on a Republican neighbor’s door—it rarely felt like you were making history. There had been no guarantee it would lead to anything. More than likely, it would end in an awkward conversation or door slammed in your face. But because millions of people I never met put aside their discomfort and took action, those moments added up to more than anyone ever could have hoped to accomplish on their own.
The morning after Obama left office, I stood on the National Mall with a clipboard to collect signatures for a candidate running for governor of Virginia.
“Hey there, are you all registered to vote in Virginia?” I called out to people headed to the Women’s March.
As strangers signed my form, I asked what had brought them to the march. Each had a personal story, even if they didn’t know how to articulate it. Some had been volunteers for Hillary Clinton, Bernie Sanders, or Obama; some had never voted before; some saw the march as totally disconnected from politics. The common thread was they wanted something to be different and realized they had a voice.
I didn’t know whether that day would lead to anything. I didn’t know that all across the country, hundreds of local organizers were putting on their own marches. Or that so many marchers would show up again, at congressional town halls, candidate recruitment forums, and neighborhood canvasses. Or that hundreds of thousands would return to where I was standing more than a year later, inspired by high schoolers to rally against gun violence. Or that my friend’s uncle in Queens would prove me wrong and that so many women—the largest number in history—would fly to Washington for their own swearing-in as new members of Congress, less than two years after Trump’s inauguration.
As with a decade earlier, all I knew for sure was that I and so many others wanted something to be different. We had seen the power of that before, which meant we could see it again.
So that morning, I held on to my clipboard and marched—one voice among millions, calling for change.
After the 2008 election, organizers scattered in hundreds of different directions. Here’s what some of the voices included in this book are up to as of fall 2019.
Yohannes went on to work in both terms of President Obama’s White House and on his reelection campaign in 2012. He is now on the faculty at Harvard.
Nathan worked on antihunger policy at USDA in the Obama administration before returning to Iowa in 2011. He lives in Des Moines, where he serves as Iowa’s deputy attorney general for policy and works to raise three kids with his wife, Andrea.
Jackie left the campaign lifestyle behind and now works in government. She still misses it, especially during election season.
Lauren is an attorney who currently resides in Washington, DC, with her husband and beautiful baby girl.
Ally went on to serve as the field director for US senator Patty Murray’s (D-WA) successful 2010 reelection campaign and Tim Kaine (D-VA)’s successful 2012 bid for the US Senate before leaving politics to pursue her law degree. After graduating from Harvard Law School, she joined the legal department of Hillary Clinton’s presidential campaign and now serves as president of the Purple Campaign, a nonprofit organization she cofounded in the wake of the #MeToo movement to address workplace harassment.
Brynne continued working on campaigns and issues that are important to her. Her love of spreadsheets continues.
Joe is happily working only forty hours a week, these days for Eastman Music Company in Southern California. He lives with his girlfriend in Pasadena, has become one hell of a cook with all his free time, and enjoys doing yoga with Nobel laureates at CalTech.
After the Obama campaign, Greg went on to serve in various roles at the White House and at the US Agency for International Development. He has since moved to New York City and is currently completing a graduate program at Harvard.
Since the campaign, Steve did stints during the first term of the Obama administration at the Pentagon, the Department of Energy, and the White House. He now resides in Los Angeles, California, working with organizations that champion diversity and social and environmental justice.
After serving eight years in the Obama administration, Bess now works in communications in the private sector on issues impacting communities at the intersection of corporate social responsibility, public policy, and human resources. She currently lives in Washington, DC, with her husband.
Anne serves as chief program officer of the Obama Foundation. Previously, she served as president of Enroll America, a national nonprofit organization that supported the effort to enroll millions of Americans in health coverage made available through the Affordable Care Act. Anne is married to Carlos Monje Jr., who served on the 2008 Obama campaign policy staff. They met in Iowa in 2007 when Carlos came from Chicago to knock on doors and contact caucus goers. They have a son, Sebastian, and live in Washington, DC.
Following the 2008 presidential campaign, Dean joined the Obama administration as a political appointee; he worked on President Obama’s health care bill and First Lady Michelle Obama’s Let’s Move! Initiative against childhood obesity. Currently Fluker is a talent agent at United Talent Agency (UTA), where he represents artists including actors, writers, performers, and musicians.
Marygrace currently lives with her four-year-old daughter in Denver, Colorado. She is the executive director of Wildfire Contact, a voter contact firm owned and managed by Iowa Obama alumni.
Rachel is the cofounder and executive director of Organizing Corps 2020. She is building the next generation of campaigners and the organizing force for the general election nominee to ensure Democrats can win back the White House in 2020.
Anna is a speechwriter at West Wing Writers, where she helps visionary leaders from fields as diverse as tech, consulting, academia, and entertainment in matching messages to moments. She lives in New York City and volunteers as a mentor for Girls Write Now, a nonprofit serving high school writers.
After starting a grassroots Obama group in the 2008 primaries, Patricia is now an elected member of the Fairfax County School Board. She teaches in Arlington and continues to be active in Democratic political organizing, though she finds her free time increasingly focused on organizing for climate action.
After serving in President Obama’s administration for seven years, Francis graduated from the University of Pennsylvania with a master’s degree in social work. He works as a primary psychotherapist for an agency providing outpatient treatment for individuals struggling with eating and feeding disorders, body image, and comorbid mood and personality disorders. He and his partner live in Philadelphia, Pennsylvania.
Lauren worked in the Obama administration at the Department of Health and Human Services and the Commerce Department. In between, she served on the 2012 reelection campaign as regional director for the Great Lakes and Mid-Atlantic region and earned a master of public administration degree from the Harvard Kennedy School. She was also a founding partner at 270 Strategies. In 2015, she married fellow Obama campaign alum Chris Wyant, and they live in Chicago with their son, Owen.
Tyler spent all eight years in the Obama White House, primarily as a speechwriter for both President and Mrs. Obama. After the administration, he supported Mrs. Obama on her record-breaking memoir, Becoming, and is now a partner at Fenway Strategies, a speechwriting and communications firm.
After the inauguration, Howli moved to Washington and spent six years working in communications for the Obama White House. Today she and her family live in the Bay Area. She still gets sunburned while knocking doors in nearby swing districts.
Esther spent eight years working for the Obama administration helping to make policy like the Affordable Care Act and the Clean Power Plan a reality. In 2018, Esther moved to Brooklyn and is hoping to work at the intersection of climate crisis mitigation, women’s business ownership, and politics.
Emily lives in Des Moines, Iowa, with her husband and their two boys. She is a co-owner and partner at the political consulting firm Wildfire Contact. In 2016 she served as an Iowa senior advisor to Hillary Clinton’s general election campaign. In 2019, she rejoined the campaign world full time as a national senior advisor and states team director for Warren for President.
Joe went on to work in the Obama White House for eight years and is currently deputy chief of staff to President Obama. He lives in Washington, DC.
After spending several years in the Obama administration, Jamal went back to school for an MBA. He has enjoyed working on teams with an entrepreneurial style similar to that of the 2008 campaign and appreciates reconnecting with some of his 2007–2008 campaign comrades each fall to play fantasy football. He lives in Atlanta.
Janice is currently living in Des Moines, Iowa, where she is working on her fourth presidential campaign—this time as Elizabeth Warren’s Iowa state director.
Following the Obama campaign, James worked for the White House’s Office of Public Engagement and Intergovernmental Affairs. He then joined an educational nonprofit led by Dr. Jill Biden. Today, James lives with his wife in his native Ventura County, California, where he works as a community college administrator.
Megan is working in Democratic politics to make sure every American has a fair shot. She is the Iowa state director for Governor Steve Bullock’s presidential campaign.
After the 2008 election, Carrianna spent nearly eight years working in the Obama administration. Shortly after the inauguration of Donald Trump, she decided to run for office herself and now serves as a member of the city council in Hyattsville, Maryland.
Simeon is a small business owner and lives in his former turf of Iowa City. He cohosts the podcast Political Party Live.
After Nevada, Maggie worked in five additional states for the Obama campaign through the general election, including Texas, where she met her now husband, Trey, a fellow Obama organizer. After the campaign, Maggie moved to Washington, DC, where she served in the Obama administration and went on to be the executive director of Generation Progress. Today Maggie and Trey reside in Raleigh, North Carolina, where she is working for Senator Elizabeth Warren’s campaign for president.
Jaci is the director of public engagement for a wind and solar energy company. She is married and living in Minnesota.
Shannon is completing a PhD in climate science at Georgia Tech in Atlanta. She hopes to combine that with her experience organizing on the campaign and communicating NASA science on Capitol Hill as part of the Obama administration to help build a world more resilient to climate change.
Jason currently lives in Washington, DC, but still keeps a toe in Maryland politics. He launched his own consulting firm, focused on accelerating action on climate change, and founded the nonprofit Civic Nation. When not engaged with those two things, he can usually be found hiking.
Chris is currently the deputy chief program officer at the Obama Foundation, where he helps oversee the strategy and operations for the foundation’s various programs. Since the 2008 campaign, he has held a number of leadership roles in government, advocacy, nonprofits, and campaigns. He and his wife, Lauren Kidwell, an alum of Obama’s 2004, 2008, and 2012 campaigns, are proud parents of Owen, who at one year old appears to be an organizer in the making.
After the 2008 campaign, Nicole went on to work at the US Department of Education, the White House, the College Board, and Bard Early College in New Orleans. Nicole is currently an independent education policy consultant based in New Orleans.
Finally, Leah, whose time as precinct captain in Davenport was her first political volunteering experience, also volunteered on the 2012 reelection before taking a break from campaigns.
When asked about 2008, she said the following:
My daughter was born during that time. I have pictures of me in my Obama shirt and my little pregnant belly. When we talk about that period, I tell her I’m proud to have been a part of it and explain why I was involved. I wanted to help make our country a better place for her. We’re lucky to live in this country, but we can’t take it for granted, and we have to be a part of helping make it better.
I haven’t been directly involved in campaigns since 2012, but I have been active in my government. I’m involved in different ways now. We didn’t have a Narcan law in Iowa. After a friend’s brother passed away from a heroin overdose, I went up and lobbied on the hill in Des Moines for legalization of Narcan. And I hope that’s the legacy my mom’s left with me—to be active and to have a voice.
I feel like Barack Obama gave me a voice in my own government. Tripp and the people like him, they taught me how to use it.