Who Thought This Was a Good Idea?

by Alyssa Mastromonaco

  So many people reached out to me after they saw the show. An older man from the Midwest said I had restored his faith in government. A wonderful woman who heard that I got my dresses from a consignment shop offered to send me her old Oscar de la Renta gowns. (I couldn’t accept them—though I wanted to—but thanked her profusely.)

  About a month later, after I had left the White House, Cutter called to tell me that her friend Anne Finucane, the vice chairman of Bank of America, had seen the interview and asked her to introduce us.

  I met Anne for tea, and she asked me about the White House and what I wanted to do for my next phase. I was pretty honest and said I had no idea. She said that I was young enough to have another big adventure and not to worry if it was a disaster, which was very reassuring (but also not). She said she would keep me in mind if she heard of anything and to keep in touch.

  A few weeks passed and Anne texted me from Cannes. “I am with Shane Smith, Bono, and the Edge right now,” she said. I thought this was a joke that would end with a priest and a rabbi. “You need to meet Shane Smith.”

  A month or so later, I went to the VICE offices in Williamsburg, Brooklyn. This was harder than it sounds; I showed up at two different entrances, both of them wrong, but I did appreciate how nice the office operations team in shipping and receiving was. I finally found my way to the main door, introduced myself, and waited for someone to come get me for my meeting with Shane. Finally, the man himself came down. I joked that his being able to identify me right away probably wasn’t a compliment; the lobby was full of people younger than I am. And with many more tattoos.

  Two months later I accepted a job as their chief operating officer. Many of my friends (and my husband) thought I was crazy; I had never worked in media before, but even if I had, this was not just any old media company. But then again, politics isn’t exactly a calm, straightforward career path, either, and I felt like I had made a real impact there. Why shouldn’t I be able to do the same at VICE Media?

  You leave the White House only once (usually), and that first move matters more than anything else. With that one decision, your personal stock either rises or falls. I hated this, but I kept thinking about what the men (Plouffe, Jim Messina) I’d worked with had gone on to do, and I felt like I had to make a similar statement with my new job. It would be a challenge, but part of me wanted to be reborn after tying my success to Barack Obama’s for almost ten years. Going into something totally new—and something that, frankly, not many people do after they leave the White House—felt like the way to do it. Besides, the energy and youthfulness at VICE made it feel like a campaign, which was a space I was comfortable in. I also very much wanted to wear whatever I wanted to work again. It was a risky move, but so was Barack Obama running for president. Right?

  CHAPTER 9

  Resilience, or A “Serious” Breakdown

  I felt so good going into my last day at the White House that I had not only packed my boxes and cleaned out my office but had had the folks who hang art in the West Wing prepare it for its new occupant, Pfeiffer.

  This feeling did not last. When you leave the White House, your security clearance disappears. Someone comes and tells you what it means to lose your clearance, makes sure you know not to ever talk about anything classified that you’ve learned in your time there, and then takes your security badge and you are done.

  This is the moment when it hit me.

  I cried and cried. One of my favorite documentaries is The September Issue, about the making of the biggest issue of Vogue of the year. In the film, Anna Wintour talks about how her dad knew it was time to leave the London Evening Standard—he said it was because he had started getting angry. I had started getting angry. For many months, I knew it was probably time to go.

  But for nearly a decade, my identity, rightly or wrongly, had been defined by the man I worked for. I knew who I was in terms of the structure of the office, and I had a good idea of what people outside the building thought of me—hardworking, critical-thinking, gets-to-yes, keeps her head down, team player, a little sensitive. That is who I was, and it felt OK to hook my identity to that because I had worked so hard to get there and stay there. And because the man I worked for was the president of the United States.

  As I was trying and failing to pull myself together, I looked at the security guy and said, “I’m sure this happens a lot?”

  It doesn’t.

  Just as I was finally calming down, the vice president came in to say good-bye. I love that guy. More tears. (From him, too!) When I eventually tried to make a break for it, Anita and Ferial came to get me for the good-bye toast in the Oval Office. I’m sure you think I’m being really douchey, but in many ways everyone hates these. Having POTUS say good-bye to you in the Oval is a once-in-a-lifetime experience—an honor—but you are also on display while you choke back tears and try to slam champagne and a chocolate-covered strawberry without getting seeds stuck in your teeth.

  But obviously if POTUS didn’t do it, you would be bummed. No winning.

  POTUS gave me a painting of a landscape in Iowa (it is one of the first things you will see when you walk into our condo; I am always too happy to explain where it came from), and when we went outside into the beautiful May evening on the lawn, the whole gang was there. Even Favs and Plouffe, who had left the year before, were back for it.

  As this was happening, I realized and actually said out loud that I loved everyone and that I didn’t know if I was ready to be emotionally independent from them. I am confident in my ability to do work and adapt, but I was not confident in my ability to support myself. Many people go through this after a long-term relationship breaks up—I think you’re an amazing person, and I only hope for the best for you! I just need some time apart!—and my leaving the White House was kind of like that. I was worried that I had spent so many years with this group of people, this dysfunctional but fiercely protective family, that I would be bereft of company. Any major, life-changing moment I’d had as an adult had been with them. (And often because of them.) Some losing, more winning, getting married. They knew it all and still loved me (usually).

  The time came to put all my boxes in my car and drive away. You accumulate a lot over eight years; after Pfeiffer helped me put everything in my car, it looked, and felt, a lot like when I was leaving for college. Bags of shoes, photos, jackets, some state dinner dresses I had changed out of in my office and never taken home. Plus, Pfeiffer and I had a special relationship; we were the same age and had been through it all, from Chicago to now, together. We had seen each other grow up.

  The send-off was like the scene from 90210 when Brenda leaves for London and says good-bye to Dylan: We told each other we were best friends for life and cried and cried and cried some more. The only thing I could do was get into the Ford Escape and drive through the gates of the White House and onto Pennsylvania Avenue one last time, listening to Led Zeppelin as loudly as I could.

  I was so sad, but I didn’t have time to be: I was booked for three parties in four days. I very briefly considered bailing on mine and Kathy’s going-away party that night—“Alyssa and Kathy’s Last-Chance Dance”—because I didn’t want to get off the couch. (It’s a good thing that I managed it, though, because we had pigs in a blanket, and I will always remember Mindy saying, “Is that the national security adviser dropping it like it’s hot?”)

  The next day, I was so hung over that David had to go to Five Guys to get me a cheeseburger and fries, but I had to rally because I was going to the White House Correspondents’ Dinner. I had an invite to the Vanity Fair party, but I absolutely could not go. (Though I didn’t miss Obama’s performance: “Just last month, a wonderful story—an American won the Boston Marathon for the first time in 30 years. Which was inspiring, and only fair, since a Kenyan has been president for the last six!”)

  That Monday, I went to the Met Ball as a guest of Anna Wintour, who invited me when she heard my White House departure date was May 2. I had a vintage Valentin
o dress that I got at my consignment shop (and had altered to fit my butt). When I went to get my makeup done at Barneys, they politely asked if I wanted my hair done as well. I told them I’d had my hair done already, and they fixed it.

  On Tuesday, I crashed. Not like I got wasted at the Met Ball—though I was part of a very early set of arrivals, 5:45 PM, and they didn’t serve food at the cocktail hour—but I got depressed. The years of adrenaline and purpose from the White House bottomed out faster than you can say “House Hunters marathon.”

  I wasn’t just eating dry cereal out of the box and crying. I took meetings. I helped out at the DNC and served on the technical advisory group that selected Philly for the 2016 convention. I was appointed to boards: the University of Wisconsin Board of Visitors, the John F. Kennedy Center for the Performing Arts Board of Trustees, HeadCount. I became a contributing editor at Marie Claire. I had been on Charlie Rose right before I left, and because of that I was able to take even more meetings. I got to have dinner with Bob Weir, the guitarist for the Grateful Dead, and talk about digitizing folk music with Mickey Hart, one of the drummers for the band.

  Even with all that, I felt like shit. I was totally lost. I had no idea who I was or what I was going to do. On days when I didn’t have plans, I would wake up, eat breakfast, watch TV, and go back to sleep; sometimes I would get dressed right before David came home from work so he wouldn’t know I had been sleeping in the middle of the day. When you go from checking your BlackBerry 500 times a day, needing to be available and responsive 24/7, to being able to sleep until 8:00 AM, wake up, have a leisurely breakfast, and do whatever you want—it sounds awesome, but you also wonder why no one is calling you. Weren’t you invaluable? Irreplaceable?

  We are all replaceable. Life goes on, but that doesn’t mean it feels good.

  To add insult to injury, about two months after I left, a reporter wrote a feature for Politico in which my becoming a contributing editor at Marie Claire was the lede—and she wasn’t saying the development was part of an exciting trend of women’s magazines covering more politics and international news. She quoted my press release about the job, where I said I appreciated Marie Claire’s fashion editorial as well as its coverage of global women’s issues, before arguing that while these two aims should be mutually exclusive, for women in power, they can’t be. In other words, any time someone like me expresses interest in beautiful clothes, or celebrities, or whatever, it doesn’t indicate that I have a multifaceted personality with a healthy balance between light, fun hobbies and intellectual, political, and professional concerns—no, this reporter said, it means I have been squashed under the thumb of the patriarchy.

  This pretty much sums it up:

  For nine years, Mastromonaco guided Obama’s political trajectory behind the scenes. In 2011, the New Republic listed her as one of “Washington’s Most Powerful, Least Famous People”; according to POLITICO, she “managed nearly every aspect of Obama’s political rise.” But even as she guided the life of the man running the most powerful country in the world, she remained typecast in the media in the two (very contradictory) roles allowed for women in public life: at once a Machiavellian maneuverer and a cupcake-eating cheerleader.

  She went on to say that a New York Times profile of me was insulting both because it mentioned the fact that my hair had turned prematurely gray so I dye it (it’s true) and because it described me as being powerful.

  I knew she was wrong, but at the same time, because I had lost my purpose, it also felt like I’d made a huge mistake. Had I thrown away everything that could or would make my life meaningful?

  I wrote an op-ed in response, which, because I was truly furious, my friend Lea had to make readable. I argued that modern women see no contradiction in being both informed and fashionable (and that men’s magazines don’t get much grief for running photos of women in bikinis alongside lengthy reportage). It ran in the Washington Post. I had spent so much time trying to keep myself (and my opinions) out of the public eye while I worked for Obama that I was incredibly nervous, but I couldn’t let her piece go unanswered. She was dismissing my choices for not being “serious” enough. But what is “serious” enough? If she had known I was also working with the DNC, or HeadCount, would that have changed her mind?

  Honestly, who cares? Between Charlie Rose and the op-ed, I was more visible than I had been in years, and I was actually proud. I had been so deathly afraid of having a profile, and of saying something that might cause trouble for POTUS, that I had assumed there was no such thing as good publicity. But in the meantime, I had learned the boundaries of what I did and didn’t want to say. I got better at talking about myself.

  I took even more meetings. If I had focused and gotten my shit together, I might have made better use of it all, but I was so overwhelmed that I often felt like I showed up to the meetings and just sat there and blinked.

  I mentioned before that Anne Finucane, the vice chairman at Bank of America, had seen my Charlie Rose interview and asked Cutter to introduce us. Even though she eventually got me a job, when I went to meet her for tea, I was really intimidated, and I didn’t feel like I was being the best version of myself. She was the one who wanted to meet with me—I should have strutted in there and dazzled her with my deep knowledge of the recession and the debt ceiling—but I felt like I wasn’t performing. Halfway through our conversation, she stopped and said, “I want you to come work for me, but I don’t think that’s right for you right now. Let me help you find what is.”

  I had read about Shane Smith, seen VICE in our Situation Room news clips, and watched the show on HBO. When we set up our meeting, I knew they were based in Brooklyn and imagined the office populated with tattooed skateboarders who talked about music I’d never heard of. And that’s about it.

  Around the same time, I signed my book deal. I was still thinking about VICE, but while I mulled it over, writing a book felt like something that made sense—many people who leave the White House write books, and it brings them glory and gravitas, and everyone goes to the book party and it’s a great time of rehashing your greatest moments. Reggie Love’s and Axelrod’s books were going to come out the next year, and Plouffe’s was published soon after the 2008 campaign. There wasn’t really a woman from the White House who’d written the kind of thing I envisioned, but I had a clear enough idea of what I wanted to do that it wasn’t daunting.

  The idea was an advice book/memoir geared toward women between the ages of about 15 and 25. Knowing Mindy made me think there should be something similar to her books, but for politics; although mine wouldn’t be as funny, I hoped it could help women see themselves working in government. It wouldn’t be chronological—because to me chronology seemed too much like you were trying to leave your legacy—but instead would be organized by qualities that have helped me in my career: leadership, preparedness, resilience, etc. It was going to be great. I had all these funny stories and important lessons that I was going to impart to my legions of readers, who would be so inspired by my story of hard work and tampons that they would be firing up their laptops to apply for Senate internships in no time. I finally had something to hang my hat on after months when there was not a single hat rack to be found.

  A friend was writing her book as I was trying to write mine, and I would talk to her about it a lot. Soon, six months had gone by, and talking to my friend was the extent of the work I’d done. Nothing. I began to worry that agreeing to do it at all had been an act of hubris. Being a writer is a profession—just like being a veterinarian, lawyer, or ballerina. I couldn’t wake up one morning and be a ballerina. Why did I believe I could wake up one morning and write a book?

  Eventually I tried to come up with a more detailed outline than what I’d turned in to the publisher, and it made me feel even worse. I realized how uncomfortable I was with talking about the White House and the president. I didn’t want to tell anyone else’s story—it wasn’t my place—so every anecdote I wanted to include, I ended up designating
as “somebody else’s” and putting it in the NO pile. I would watch old campaign videos to get myself psyched up, but they just filled me with dread.

  By early September 2014, I had written an introduction and a first chapter. I was feeling a little better, but still—not great. It was OK, though, because all I needed was to get it done so that it could come out in the spring of 2016—the last graduation season when Obama would still be in office. I had plenty of time.

  Meanwhile, I had begun to negotiate my contract with VICE, and here, too, I was out of my depth. I had only really worked on campaigns and in the government, both of which have transparent pay scales; salaries are publicly disclosed and reported in the Washington Post every July 1. You know what every single person in the White House makes. I had even more insight because I managed the salaries.

  So I was completely unprepared to negotiate my offer at a private company—it didn’t even really occur to me that it would be different. Since VICE had this cool-kid reputation, I didn’t want to roll in with my big-deal DC lawyer, Bob Barnett, who had negotiated my book deal. Against the advice of David, who knows what he is talking about, I did it myself, with some solid input from Kathy Ruemmler.

  Out of left field, VICE asked me what I thought I should make. If anyone ever asks you this—and they probably will—do not give a number. Sometimes employers will ask what your current salary is, and unfortunately, you cannot fib there; if they call your reference and it’s your boss, they could find out what you’re making now and know you’ve lied, which looks so much worse than working for a lower-than-average paycheck. But if anyone asks you to tell them what you want, you should respond as follows: “I’m sure there’s a salary band for the position, and my hope would be to come in at the high end of that.”