I graduated HLS in 2006, during President Bush’s second term, and began a clerkship the following fall. While clerking, my then-fiancé, Jen Cannistra (HLS ’05) and I decided to join a Democratic presidential campaign when we finished because working to elect the next President felt like the most important thing we could do.
We quickly decided to support then-Senator Obama. He was not the front runner. His campaign was NOT the one to join to advance your career. We believed he could win, but knew it would be hard. I am a firm believer that campaigns are too hard and too unpredictable to do it for anyone other than the person you think should win. Your heart has to be in the fight.
We started looking for jobs by contacting anyone we knew who was remotely connected to the campaign. We originally thought, given our law degrees, that some kind of policy or legal role made sense. We soon learned we were wrong. What the campaign really needed was boots on the ground. In the end, our key contact was not a HLS prof or fancy alum, but a recent college graduate whom Jen knew from being a resident tutor at Kirkland House. He was doing advance at the time (specifically, luggage) and got our resumes to the early states. Luckily for us, the Nevada field director expressed interest in hiring us as field organizers.
We got back from our honeymoon, found out we had jobs, and drove cross country in September 2007. We were in Las Vegas through the Nevada caucus, then went to New Mexico, Texas, Mississippi, Pennsylvania, and West Virginia over the course of that long primary campaign.
Organizing is hard work. You never have enough time, people flake, and you are accountable for hard metrics. We felt a deep sense of responsibility, which created its own stress. At the same time, organizing can fuel you. You meet Americans from every imaginable background who are making democracy work. You knock on doors, call strangers, and build teams of volunteers to make more calls and knock on more doors. It can be magic.
After the West Virginia primary, we were ready for a change. We reached out to someone from Nevada who had ended up in the Chicago HQ, and asked if he could help us find something there. He did, and we moved to Chicago to work on a vetting project for the period between the primary and the general.
One day, I saw in headquarters a prominent Democratic figure who was rumored to be planning for transition, which was work that had always interested me. I nervously emailed the policy director for the campaign, whom I sat near but barely knew, to express interest. She offered to help, and I ended up being the first paid employee of the then-secret Obama-Biden Transition Project.
Six of us worked in a dingy office above a Subway on Capitol Hill. Many others worked in other silos. I did some legal research and helped organize the promises we had made over the campaign–so we could keep them. After the election, I worked as an assistant on the transition. My boss there recommended me to the incoming White House Counsel, who hired me. I spent three amazing years in the White House Counsel’s Office before leaving government.
A couple of quick practical notes: First, as a field organizer, I made an annualized salary of $24,000. LIPP was essential. Second, your HLS degree gives you a huge safety net to try something like this: if things didn’t work out, I knew I could return to the firm I had summered at or another opportunity. You should feel emboldened by the fallback options you have.