Who Thought This Was a Good Idea?

by Alyssa Mastromonaco

  No big deal, right? I went apeshit. After all I’d been through that election cycle, whoever had talked to this reporter had characterized my job as “basically a travel agent.” I had always been very sensitive about this idea that I only handled “travel and logistics”; I also felt that, if someone had been describing what Jim Messina had done in my position, they would have said he ran the White House.

  I don’t want to blame my reaction on fatigue, but it didn’t help. The press office had circulated the story to senior advisers, and as soon as I read it, I replied-all with a very cutting, infuriated response. I thought it was totally warranted. In a show of solidarity, Kathy Ruemmler, the White House Counsel, my dear friend, and the woman who, at 35, delivered the closing arguments in the Enron case, also replied-all and echoed my sentiment, saying she agreed with me. It was extremely disappointing, we said, that we weren’t having each other’s backs. You don’t talk about your colleagues on background, and you definitely don’t on-the-record them. If a reporter approached you, it was understood that you would flag it for comms.

  After that, I let it go; I was fuming, but I didn’t think it was a big deal—sometimes you just have to say what you want to say. I figured people would read my email, maybe whoever said what they said to the Times would feel bad, and that would be enough.

  The next morning I came in for the 7:30 senior advisers meeting, and Clay told me that POTUS wanted to see me.

  Walking to his office, I had no idea what he would want to talk about, but being called down to the office rarely meant anything bad. I wasn’t nervous, so I just went in.

  “So,” he said, “I hear you sent quite an email.”

  I was totally taken aback. How the hell did he know about the email? I instantly started going over that distribution list in my head to figure out who had narc’d on me.

  I wear every thought on my face; POTUS knew immediately that I was mentally rating each person on my team on a scale from innocent to “deserves another irrational email.” “It doesn’t matter who came to talk to me,” he said. He went on to say that I needed to realize the power of my words. I could not send emails like that because they—I am paraphrasing—freak everyone out.

  Developing self-awareness is a lifelong process; you don’t just wake up one day and have all you need. So even though I’d spent the last few months demonstrating that I was capable and knew what I was doing, this was something of a revelation. When the president of the United States tells you your words are powerful, it can be pretty shocking. I honestly didn’t think anyone would give a shit if I sent a snippy email.

  It was good advice, specifically to me at the time but generally as it relates to any kind of replying-all in life: Think about how what you say could affect people, from the top down. It was also a wake-up call for me about my state of mind: I didn’t know why (yet)—though I’m sure I did, deep down—but my temper was getting worse, and my fuse shorter and shorter.

  CHAPTER 5

  Some Personal Shit You Should Probably Know

  Sometime in early August of that year, Plouffe was in my office and we were shooting the shit. Since I am a master typist, I was looking at him, talking, and typing an email at the same time, which I might have done on any given day. But as he was leaving, he got this worried look on his face. He furrowed his brow in a very classic Plouffe expression and asked, “What are you doing?”

  I looked at the computer. Nothing I had typed made sense. It wasn’t even words.

  I had been losing things lately. I had misplaced my keys. I would get in the car and not remember if I had fed my cat, Shrummie. I had misplaced my beloved binder more than once; I had even left it at home one day, which I had never done before in my life. Earlier that summer I forgot that I had already put my NuvaRing in, put a second one in, and didn’t realize until I got my period and two Nuvas popped out. (Luckily that explained the historic adult acne I had developed that month.) When I saw the nonsense on my screen, all this came together, and I panicked. I was convinced I had a brain tumor. I also, apparently, didn’t realize I had started talking to myself, because after Plouffe walked out, my assistant, Brundage, heard me talking—saying what, I don’t know—and called the White House Medical Unit. He told them I was on my way and sent me over. I walked past the Rose Garden and down the Colonnade fighting back tears.

  Working in the White House is incredible, but it is also completely, totally exhausting—and exhausting isn’t even descriptive enough. You set your alarm for 5:00 AM and wake up only to assess the state of your hair; “It looks fine,” you decide, and go back to sleep until 5:15. You wake up at 5:15 and negotiate with yourself that “fresh faces are beautiful,” to get in that second tranche of 15 minutes. Working for the president got me to stop wearing makeup altogether; it’s becoming popular now, but back then you would come in with nothing on and everyone would ask if you were sick. You told yourself the dark circles made you look like an operative working in the Green Zone, even though you really lived in Georgetown with a nice man and a Persian cat.

  The absolute best part is the White House Med Unit. Doc Jackson calmed me down and gave me a complete neurological exam. I was so panicked I don’t remember much of it, but I think he tested my reflexes and coordination, and I walked back and forth a few times. He concluded that due to extreme exhaustion caused by lack of sleep, I was operating at about 50 percent of my capacity. I agreed I would go to sleep—not just be in bed, but, like, snoozing—by 10:00 PM and take Ambien for a few weeks. It was the first time that I admitted to myself that I might not make it two full terms.

  I first talked to POTUS about possibly leaving the White House a couple of months later, shortly after his reelection. We were on AF1 on our way back from a trip to Asia. I wasn’t certain I wanted to leave right at that very moment, but I felt it coming, and for all the opportunities Barack Obama had given me, I felt like I should let him know what I was thinking. It wasn’t easy; I didn’t want to seem like a wimp for opting out, and also, once you say something like that, you can’t really take it back. He told me he believed I just needed a vacation and that I should take one; he didn’t sound disappointed or judgmental. I agreed to take a break around the holidays.

  Unfortunately, that break didn’t come. The person I thought would travel as acting chief of staff couldn’t go to Hawaii with the first family, so I had to go. We thought this would be an easy year, for once, but the White House and Congress were still heavily negotiating the ability to raise the debt ceiling—if it wasn’t raised, it would have been cataclysmic for the economy and our standing globally. We were also in the middle of nominating a new secretary of defense. I had to go.

  Here is your opportunity to roll your eyes at my being sad about spending Christmas in Hawaii. I get it. I always try to be present and aware of my situation and surroundings; when I spiral into self-pity, I know there are people far worse off than I am. In general, I probably suffer from what my friend Anne would call “uptown problems”; these have also been called “first-world problems” and “privilege,” but no matter which term you use, it means the same thing: It’s not that bad.

  But I was totally spent, and I felt incapable of working any more. I also really, really love Christmas. The German side of my family instilled in us early on the importance of a grand spread with many types of meats and cheeses and cake. It would be the first year—ever—that I wasn’t with my family. Even during the campaign in 2008, I flew home for Christmas Eve dinner and went back to Chicago on Christmas Day. I was almost devastated about having to go to Hawaii, though Nancy-Ann DeParle, the deputy chief of staff for policy, did get me an amazing sweater with a cat on it that I was really looking forward to wearing on the plane.

  We were leaving on a Friday. I had been dating the nice man in Georgetown, David, for a little more than two years, and since we would be spending the holidays apart, we decided to go to our spot, Cafe Milano, for a preholiday dinner on Thursday night. David was chief of staff to Senate Majo
rity Leader Harry Reid from Nevada, so it wasn’t particularly upsetting that we weren’t going to be together—he would have to work anyway.

  I was late, it was pouring rain, and we sat down next to the loudest people I’ve ever encountered. By the time my food came, I was laughing, because nothing was going right and we didn’t get a chance to say basically anything to each other the entire time.

  We finished eating, and David asked if I wanted dessert. If anyone ever asks you if you want dessert in a restaurant, something is up. Who orders dessert in a restaurant? Unless it’s a special occasion or they need more time to tell you something bad, no one orders dessert in a restaurant. I remember saying very clearly, “No, I just want to go home and take my Spanx off.” (Update: I have not worn Spanx since leaving the White House.) We walked outside.

  Down the street from Cafe Milano there is a little brick building that contains a Domino’s Pizza. In front of this Domino’s Pizza, in the rain, David asked me to marry him.

  David had three rules in life, and he would often recite them, I thought, to make it clear that we would never get married. The rules were: (1) rent, don’t own; (2) no pets; and (3) never get married. I never harbored those romantic-comedy illusions that I would be the one to change him; I was totally shocked. First by the proposal, and then by the giant ring.

  We walked home (still raining), and I called my family. David’s phone rang. It was Jack Lew and Rob Nabors to talk about the debt ceiling. He got on the phone with them, told them we had just gotten engaged, I heard a “Mazel tov!” through the phone from Jack, and then they talked about the debt ceiling.

  I emailed Pfeiffer to tell him, and he wrote back saying he had read my email as “I got enraged” before he realized it said “engaged.”

  The next day, I left for Hawaii. We were announcing that John Kerry would be the next secretary of state, so he was in the West Wing when we met before the trip. He and Mrs. Heinz—also our neighbors in Georgetown—were so pleased to hear about my engagement. The vice president came in for hugs. Tina Tchen, the first lady’s chief of staff, got misty-eyed. VJ, too. And there were Dey, Jess, and the whole SkedAdv gang. On AF1 a few hours later, the first lady insisted on seeing my ring and having a glass of champagne to kick off the trip. When we landed, I found my room had been decorated for Christmas by the advance team, complete with a small tree and lights.

  I was feeling a lot better; I don’t like attention, so the whole celebration made me uncomfortable, but I also felt so loved. In my euphoria—and impending jet lag—I decided that my second stop at the Westin Moana Surfrider should be to get my nails done. If I was going to be showing off my ring finger, it should at least have tame cuticles! I didn’t look at the prices and ended up spending $400 on a really boring Ballet Slippers mani-pedi.

  I had a mai tai with Eric Schultz, the White House associate communications director, and went to bed. We had a daily call about Chuck Hagel and his nomination for secretary of defense, and it was at 4:00 AM Hawaii time.

  That is working at the White House in a nutshell: For every glamorous state dinner, every surreal conversation about ’80s music with a foreign dignitary, every glass of champagne on Air Force One, there is a 4:00 AM conference call. The advent of BlackBerries and the 24/7 news cycle—neither of which was really around when I first got into government—ensures almost no meaningful rest. My hair had turned completely white from stress. That’s just how it is. You kind of know what you’re getting into when you start, but you also have no idea what it will really be like.

  If one of my goals in writing this book is to get more women interested in and excited about working in government, then this is the part where it starts to get difficult, because I have to be honest about what it’s like to work in government. For me, anyway.

  At any high-powered job, you’re going to have to work a lot. America is a nation of people who work a lot and of people who strive to work a lot. The best thing you can be, our culture tells us, is “at the top of your field.” You are supposed to want to have power, to be an executive with a cushy corner office and a lot of money and an assistant, a person who travels for business and takes working breakfasts, fork in one hand and cell phone in the other. When I worked at the White House, this was my life, minus the corner office and the large quantity of money, but with the added bonus of being able to do something I really loved for causes that I really believed in, with people who taught me something new every day, if not every hour. Saying you love working for a politician often makes you seem like a shill, or full of shit, but I truly loved working for Barack Obama, and I think he’s one of a few politicians for whom that kind of statement is believable. I loved being a part of an administration that I thought was making the country better, and I had an incredibly generous, kind, and helpful boss who I felt had not only my best interests at heart but also the entire nation’s. Plus, when I traveled for work, I took Air Force One, which never got old, and instead of wasting time at boring conference centers I was doing things like eating goat in the courtyard of Hamid Karzai’s palace. They wouldn’t let me inside because I was a woman and they didn’t believe I was actually part of the senior staff that was cleared to go in, but still: Not much is cooler.

  So for a long time I worked at my capacity, or over my capacity. It didn’t really matter—I was young, and I was happy to do it. I had never imagined I would make it to where I did, especially not as soon as I did, so I felt like I had to do whatever it took to make sure the faith POTUS—and Pete Rouse, and Plouffe, and all these other people—had in me was not misplaced. I always found this to be extremely rewarding. To be able to prove to yourself that you can work more, and at a higher level, than you ever would have thought possible is motivating in itself. Truly believing in what you’re doing helps.

  But when I was promoted to deputy chief in January 2011, a lot about “my personal life”—which bled into my work life, as it often does at jobs that maintain even just normal hours—had to change. In my first month as deputy chief, the Egyptian president, Hosni Mubarak, was deposed. That day was also Gibbs’s last in the White House, and I couldn’t go to the good-bye karaoke party until we got a group of American citizens (“AmCits” in national security speak) out of Cairo.

  After that, I pretty much stopped going out with people from work, or really going out at all. David and I were dating by this point, but we weren’t that serious; we went out twice a week, usually to this Chinese restaurant in Dupont Circle, Meiwah, on Wednesdays and to somewhere fancier on Saturdays, until we got engaged. I didn’t make other plans because I got to work at around 6:45 in the morning and just wanted silence when I left by 8:00 PM; I also didn’t want to have to cancel on people if something came up. I didn’t necessarily have a ton of STUFF to do, but I always could have had something to do, at any moment of any day. So when I wasn’t in the office, I stayed in my apartment, waiting. I had two secure phones—the top secret phone, for really-not-good matters, was red—and a secure computer in my bedroom. They made it extremely warm.

  I never felt like I was missing out. The pressure made me grow and learn and all that good stuff, and although my old job, as director of scheduling and advance, was much more fun, my new job meant that my colleagues began to see me in a different way. Even Dey, who had been with me basically since the beginning of my time with Obama, reported to me differently. People stop seeing your interactions with them as playful banter; they start getting serious around you. The tenor of respect shifts. It’s not worse or better—but it is different.

  It was also difficult to have friends, or date, with so much responsibility. For one thing, I had had a very personal relationship with POTUS for many years; people would always ask me things like “Did he really quit smoking?” or “Who came to his birthday party?” as well as questions about insider government information, and I couldn’t answer any of them and maintain his trust. (I had also taken an oath.) When I did go out, I didn’t really drink, because I was afraid I’d say some
thing I shouldn’t. I had a roster of stories that I would tell at parties that weren’t with White House people—though I rarely went to those—and I wouldn’t go beyond that. At my first White House press dinner, I didn’t drink at all. There were hundreds of reporters in a room—you have two glasses of wine and tell a funny story and then all of a sudden you’re a “reliable source.” It was the loneliest time of my life.

  When I started to wear down, I didn’t really know what to do. Most people leave the White House after about three years because it’s so draining, but I felt this emotional, personal connection to everyone there—we all did—and I didn’t want to let them down. It’s also strange to have such a weighty job when you’re really young—it’s hard to imagine what you’ll do afterward. You have a skill set, experiences, and knowledge that very few people can also say they have. You feel like you can do anything but also like there’s nothing else you can do. Meanwhile, the stress is taking its toll on you—physically, emotionally, everything.

  When I turned 35, Reggie Love came up to me in the Navy Mess. “Boss, happy birthday!” he said. He doesn’t forget a birthday. “Did you know that, according to CNN, you are of advanced maternal age?”

  Reggie and I had been working together since he started as a Senate intern in 2005—we were tight. This was a weird thing for him to say, and I was a little… surprised… but it was fine. (After all, it was true.) All the junior staff people in the Mess were shocked; I had to tell them it was OK to laugh.

  At panels for women in government or women in media or any other type of panel that I might be on (it’s usually about getting more women represented somewhere), I’m always asked about children. Do I feel like I sacrificed having kids to pursue my career? Was it hard to make that choice? What do my parents think? And when people finally seem to have exhausted this invasive line of questioning, they add, “Are you sure?” As a childless 40-year-old woman, I am either supposed to regret not having kids or be entrenched in the expensive and often disappointing process of IVF.