Education, Culture, Art, economy

After I became Illinois Senator Barack Obama’s adviser/ director of scheduling in late 2004, [chief of staff] Pete Rouse became my spiritual guide and mentor.

Pete had worked on Capitol Hill for about 40 years, many of those as chief of staff to Senate majority leader Tom Daschle, and was known as the “101st senator” and “mayor of Capitol Hill.” He knew everyone and didn’t like talking to any of them. Walking the halls with him always involved some commentary on the people he considered to be violating his personal space.

There is no one more thoughtful in the way he gives advice. He returns every e-mail, makes every connection, and does it all while being a wheeler and dealer. His code name in the White House was “Possum,” which is why from here on out, he will be referred to only as Possum. Also, he loves cats.

When we got to the Senate, Possum drafted one of his famous “strategic plans”—lengthy, painfully thorough memos about how to get something done. In this case, it was the strategic plan for Senator Obama’s first year, and it could be summed up as “workhorse, not show horse.” It included lots of time with constituents and in Illinois, and less time with D.C. insiders and celebrities. Obama was quite fine with that. Every decision we made had to stand up to the workhorse vs. show horse test.

Obama had a political action committee called the Hope Fund that was right down the street from the Hart Senate Office Building. The Hope Fund ran initiatives for getting young adults from diverse backgrounds into community organizing and politics; it also managed Obama’s political engagements. I had been working in the Senate office for a little over a year when Possum decided that I should replace the Hope Fund’s outgoing political director, who was moving to Paris.

Initially, I was psyched. I thought “political director” was an awesome title. I would be lying if I said I really knew what the job entailed, but I trusted Possum to know what was best. Before I was offered the job, I had been working in the back office with Favs [Jon Favreau, speechwriter], Tommy Vietor [spokesman], Possum, and [press secretary Robert] Gibbs. I loved it there. We sat near the back door of Senator Obama’s office, so he would come out and visit with us a lot. Sometimes he would come to talk about policy issues; sometimes he and the guys would talk about sports. (I would chime in about gymnastics, swimming, and ice-skating during the Olympics, but that’s about it.) On occasion, we might have a little squabble over Mariah Carey.

(The specifics of the squabble are classified.) I think it was back there that we all really developed a bond. One night during a vote-a-rama—what usually happens before the Senate breaks for a recess and they vote on measures late into the night to get everything done—Senator Obama came out the back door and walked in on me doing sit-ups on
the floor. Most senators would have been appalled; he said, “Good for you.” On Friday mornings, after a bad Thursday, Tommy and Favs and I would get French toast from the cafeteria. On Friday nights, the bros and I would get the $7 Maniac Special (tempura, sushi, and some teriyaki) at Kyoto.

After I reflected on all the good times we’d had in Obama’s Senate office, I had a meltdown. The prospect of moving three blocks down the street to work at the Hope Fund filled me with dread. Why? I had a lot of bad reasons.

I was happy for the promotion, but it was definitely outside my comfort zone. I don’t love talking to people I don’t know, and this job would put me in charge of our political engagements for the 2006 midterm elections; I would also manage Obama’s profile and relationships. That was a lot of responsibility, and it would be the first time I was really at the tip of the spear—this was going to be my first experience being The Boss. I did not get the impression that the Hope Fund staff was psyched I was coming down there, either. I had no reason to feel that way, but that didn’t matter!

I dragged out the transition for a few weeks. Each time someone asked me why I was still in the Senate office, I had a different excuse, but I never deviated too far from, “Wrapping up a few projects!” I thought I had everyone fooled—until one day when Possum called me into his office and asked, “Why the hell are you still here?”

As soon as he asked, I started to cry. That’s right. I cry a lot, but I generally think it’s not OK to cry in front of your boss. If you’re feeling real emotion about something that merits strong feelings, fine, but at best, you come off as “sensitive,” and at worst, you seem like you’re trying to use your tears to get what you want. I told Possum I was afraid to leave; he told me I had one hour to pack my stuff and get to the Hope Fund office, three blocks away from $7 Maniac Fridays and all my friends.

This was NOT a big deal, but I felt like it was. I argued that I was probably too important to leave the Senate office, that Obama needed me nearby (he didn’t), and that I should probably stay. Possum told me again, loudly, to get out of the office and start my new job. He was mad. I knew he had decided to move me over in part because it would benefit me—undoubtedly, I would be able to grow and develop a new skill set. I was being my own worst enemy.

One of my main goals in writing my book is to give you the permission to admit to feeling or doing things that are silly; once you do, you can get on with your life. So here it is, the real reason why I didn’t want to go down the street: The crew at the Hope Fund had been together since the Senate race in 2003. They were all friends, and I really didn’t want to be the new kid.

Often, when you’re dreading something, it can feel as if there is just no possible way that whatever you’re dreading will actually happen—as if some goddess of serendipity will surely swoop in and stop it in the nick of time. The test you haven’t studied for will be rescheduled for next week; the guy you’ve really been meaning to break up with will tell you he’s decided to move to India to embark upon a life of meditation but will always love you and remember the times you shared; the cockroaches in your apartment will be revealed to have been a very involved art project your roommate was working on, so you’re not going to have to argue with the
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