Who Thought This Was a Good Idea?

by Alyssa Mastromonaco

  When we got to the court, David was looking cool, calm, and completely the opposite of me, so I freaked out more. As we were getting ready, he came over to me, smiling and nice and the way you would want a man to be on the day he is marrying you, and said, “I got you a gift.” I was so stressed that I hissed back, “I didn’t fucking get you anything!” How dare he get me a gift? For some reason, he gave it to me anyway; it was a pair of diamond earrings. I felt awful.

  Justice Kagan had decorated her office with a “Happy Wedding!” sign, gotten a bottle of champagne, and put out an orchid (a symbol of love). She asked us what vows we wanted to use.

  I was not prepared for this. “What are the options?” I replied. She showed them to us, and I was so overwhelmed that I just said, “What’s the shortest one?” David was completely horrified and possibly questioning his choice to spend the rest of his life with me. I started drinking the champagne as soon as we had said our vows.

  From the Supreme Court, we went back to the house, got our bags, took a picture with Shrummie, and went to stay at the Capella Hotel in Georgetown. We had dinner at 6:15, and I fell asleep by 9:00.

  There’s not a real resolution here, except the lesson that you should be able to accept the fact that sometimes you’ll fuck up, have to sincerely apologize, and try to move on. The next morning, I woke up and watched the Ina Garten Thanksgiving special and felt normal again, except for being extremely embarrassed. We went back to our house—our honeymoon in New Zealand was booked for a few weeks later—and I said I was sorry for acting so ungrateful and unhappy; I didn’t feel ungrateful or unhappy. I keep trying to find a place to wear the Valentino, but I feel like it should be in front of David, so it remains in my closet unworn.

  CHAPTER 8

  Risk-taking, or Ah-LEES-ah Goes to Brooklyn

  We take a lot of different kinds of risks in the course of a day or a lifetime, but I tend to divide them into everyday, experiential, reputational, and personal/financial. Here are some examples:

  EVERYDAY:

  • Crossing the street against the light

  • Stopping for coffee even though you know it might make you late for a meeting

  • Getting a new haircut or trying a new salon

  • Bringing up a new idea in a meeting without having bounced it off anyone

  EXPERIENTIAL:

  • Eating street meat in Bombay even though you suffer from IBS

  • Going to Japan to visit your friend David Fogel and traveling the entire coast on a motorcycle for two weeks (we got pulled over only once; you can’t ride two-to-a-bike in Tokyo, but everywhere else it’s fine!)

  • Singing karaoke

  • Going to a birthday party at a multifloor dance club and letting a man who says he’s a Welsh paratrooper walk you home

  REPUTATIONAL:

  • Agreeing to write a book

  • Defending a friend who is being attacked on Twitter when you know only half the story

  • Praising an article you didn’t read all the way through

  • Working for a candidate or campaign

  PERSONAL/FINANCIAL:

  • Breaking up with a boyfriend or girlfriend

  • Quitting your job, or not accepting a “good job” that isn’t right

  • Moving to a new city

  • Going back to school

  I was getting ready to leave the White House right around the time I got married, at the end of 2013. I felt like I had no choice—I was exhausted; I was irritable; I couldn’t sleep without Tylenol PM or Ambien; I hadn’t had a good idea in months. But I was still very nervous. I talked about it to only a handful of people outside before I actually announced I was going to do it.

  As I was preparing to resign, friends were other-level generous in setting up introductory meetings for me with people in various industries around the country. They had to be discreet, since it still wasn’t public that I was leaving, but they were still so helpful.

  I knew Anna Wintour from working with her on Obama’s 2008 and 2012 campaigns, and she was one of the supporters I was lucky enough to build a relationship with. She developed our Runway to Change and Runway to Win programs, which had designers producing Obama merchandise. (We sold out of them in record time; I still wear my Tracy Reese sweatshirt.) She gives advice the way you want it—straight. When we met for tea the winter before I announced I would leave the White House, she told me it was “time to go on to something new” and said if anything came to mind, she would let me know. Then she finished her tea, put her sunglasses on, and went to her next meeting. She calls me “Ah-LEES-ah.”

  About a month later, after I had announced my resignation and was preparing to leave later in the year, I got an email from her saying she’d sat next to Bill de Blasio—who had just been elected mayor of New York City a couple of months earlier—at a dinner and given him my number. How killer—she really was thinking of things I might be good at.

  As I was reading her email (at a stop sign with no one behind me—don’t text and drive), the phone rang through the Bluetooth on my car. It was a 917 number.

  Bill de Blasio on the blower!

  He introduced himself and said he thought I might be a good candidate to be commissioner of New York City’s Office of Emergency Management (OEM). Would I come speak with him?

  The OEM, or, now, NYC Emergency Management, and its team—responders, planners, watch commanders, logisticians, community outreach, communications, and other staff—is responsible for planning and preparing for emergencies, educating the public about preparedness, coordinating emergency response and recovery, and collecting and disseminating emergency information. I had learned so much about emergency management while working at the White House, and it was one of the things I had enjoyed most—it was a way to have a real and immediate impact. But OEM had historically been run by a military chief or a captain (men). There was a part of me that worried, rightly or wrongly, that taking the helm of OEM might be the makings of the next installment of Legally Blonde. But that had also always been my thing: small but mighty, cheerfully girlfriend-y but hardworking, only an asshole when vitally necessary. I was imagining myself wearing a puffy vest and wellies on the cover of New York magazine already.

  I set up a time to go see him the following week, and when I got there, I found City Hall pretty exciting—people getting the people’s work done. It’s also quite beautiful. De Blasio is famous for running late, and this day was no different, but Jess had left the White House and was the deputy chief of staff for the mayor at the time, so I chatted with her for a bit as I waited.

  By the time he was ready to meet with me, he was very rushed. Or at least I felt like he was rushed. One thing about Obama: He deeply believes in running on time, and we worked very hard to set up his days so that he would. He never wanted people who traveled to come see him to be kept waiting.

  I was a decidedly outside-the-box choice for this job. I had earned the respect of the Secret Service and members of the WH Military Office, but while this, too, was an agency that had been always been led by men in uniform, I wasn’t assured the same result here. In the White House, I built the relationships that made me successful for two years before I took the helm.

  I had a list of questions for the mayor; the most important was “How would you set me up for success?” Generally, if you’re coming in to take over a department, you want to know that your boss will demonstrate to everyone else that you have his or her support. You also want to know whether you get to hire people or make staffing or structural changes.

  De Blasio’s answer did not make me feel better; it was something to the effect of “They [the OEM staff] would need to get with what’s happening.” Still, I put that aside; this was a big and important job that I felt would take my career to the next level. If I was successful, I could really make a difference. If not, everyone in New York would blame me for a future hurricane. And they might not be wrong to do so.

  As we were winding down the
conversation—him checking his BlackBerry throughout—he cut to the chase pretty quickly and asked if I would want this job, and he added that he’d need me to start no later than May 1. This was an aggressive way to close, since I had said I was interested but that was about it; I was by no means in love with the idea. I explained there was no way I could leave the president and be installed in New York by May 1. I had promised POTUS I wouldn’t leave until May, and I also needed a fucking break.

  De Blasio said something like, “POTUS had you long enough, and he needs to let you go. It will be fine.”

  I was speechless. My eyes darted around his office looking for something to focus on. I was biting the inside of my cheek to avoid saying something rude. Was he talking about my POTUS? There was no way I was going to (1) leave POTUS earlier than I said I would; (2) work for a person who wanted me to let down my old boss—a man who, in addition to having given me every opportunity in the world, was the president of the United States; and (3) not take a break between jobs.

  I made Jess walk me out and told her that the conversation had given me a stomachache. It was sunny but cold. I was starving because I hadn’t eaten breakfast before the meeting, and I had waited so long for the mayor that I was now overdue for lunch. The streets were slushy, but I walked for a bit before sitting down. I was very concerned about what I would do—and who I would be—when I left the White House, and this had seemed like such a perfect, meant-to-be opportunity. It was really disappointing.

  Even if I could have managed without a break (that would have been crazy) or asked POTUS to let me leave as soon as possible (he would have said it was OK, but that’s not how I wanted to go), I couldn’t take a job where people’s lives were in my hands and I didn’t feel confident that I had what I needed to be successful. It was a risk I didn’t want to take. I had worked hard to build a reputation, and I wasn’t going to throw that away—I knew there would be another opportunity. I hadn’t always believed that, but the older you get, the more confident you can be about what you’re good at. The more places you can see where you belong.

  On that same 36-hour trip to New York, my friend Maneesh was hosting an event for one of his companies, and he invited me to be interviewed by Charlie Rose. It would be off the record but in front of a live audience of about 200 entrepreneurs.

  I agreed, obviously—I mean, it was Charlie Rose—but I was wary. I hadn’t done an interview in years, and Charlie is such an icon; I was probably more worried about looking like a ditz in front of him specifically than I was about fucking it up in general. I killed a glass of sauvignon blanc to chill me out, and the show was under way.

  It was a great interview. After the first five minutes, it felt like I was talking to an old friend onstage. (This is, I suspect, because Charlie Rose has been interviewing people for decades and is extremely good at it.) At the end of the event, Charlie invited me to be on his show. I was very flattered, but I assumed he was being polite. His office followed up the next day to lock in a date for me to appear as a guest for the entire hour on The Charlie Rose Show.

  This was more than my brain could handle. My last television interview was after the Obama Exploratory Committee launched in early 2007, and our deputy press secretary, Bill Burton, convinced me to do a spot with Chris Wallace for Fox News Sunday. He said it would be “easy,” “fluff,” “light”—10–15 minutes max. I asked what kind of prep I needed, and he said I “would be fine.”

  Luckily, I did not take Bill’s word for it. I called my friend Stephanie Cutter and told her that I had agreed to do Fox News Sunday. Cutts is a media consultant and excellent herself at TV. She understood the gravity of the situation and gave me a crash course on how to answer questions I didn’t know the answer to. Cutts is kind of like Liam Neeson in Taken; she doesn’t sugarcoat. She didn’t tell me that I would be fine. She said, “This is going to be hard and here is what you need to do to survive.” (To survive, any time you get tripped up, just say, basically: “I agree with Barack Obama’s stated position.” Works in all situations, not just on TV.)

  My Fox segment went on for more than 60 minutes and included questions on Iraq and Afghanistan. By the middle of the interview, I had sweat all the way through my Rebecca Taylor T-shirt and thought for sure I had pit stains on my jacket. At least it wasn’t live. They edited the 60 minutes down to seven, and it wasn’t horrible, but it definitely wasn’t good. Did I really want to do that again?

  When I did the risk-reward math, this was worth it: It was Charlie Rose. I set the date and became increasingly edgy every day that passed as it got closer. I thought about viable excuses to cancel. Every time I casually mentioned that I would be taping the show, someone would ask how I was getting ready for it, which was annoying, because I had really meant it as more of a “Honey, does this dress make me look fat?” kind of comment.

  A few days before the interview, some of the comms team came by my office for a prep session. They drilled me on POTUS positions, gave me stats on how many people had signed up via healthcare.gov, and told me how to frame information on recent polls (which weren’t great for POTUS).

  I kept getting very flustered. I felt like everyone was looking at me (they were), and I got antsy and uncomfortable. There was something about not having the answers at the tip of my tongue in front of a jury of my peers that was making me feel like a fraud.

  After it was over, my assistant, Clay, and Joe Paulsen came in to my office and sat down across from me. They told me they had ideas on how to make me feel better. I told them I was open to anything.

  A few hours later, Clay and Joe came back with a questionnaire. It was huge—about 15 pages long. They told me to take it to my favorite Thai restaurant, get a glass of wine, and fill it out.

  Favorite TV show, last book I read, and what I do all day—the survey was basic in many ways, but so helpful. When I realized my favorite TV show was The Mindy Project and the last book I had read was Is Everybody Hanging Out Without Me?, also by Mindy Kaling, Clay pointed out that it made me sound a little too fangirl, even if it was true and even if she was a friend.

  (A perk of my job: Once, POTUS was doing an event at the Waldorf in New York, and she happened to be there at the same time. It was very hard for me to finish a book while I was deputy chief, so everyone, including Obama, had seen me carrying around Is Everyone Hanging Out Without Me? for weeks. After the event, I was at dinner with POTUS—when you traveled with the president, he would usually request that a couple of people have dinner with him—and Bobby Schmuck, an adviser, came over to ask if he wanted to meet Mindy. I freaked out, Mindy came over, and POTUS said something like, “Actually, the person you should really meet is Alyssa.” From then on we were friends.)

  Anyway, I told Clay that the book I had finished before that was Are You There, Vodka? It’s Me, Chelsea, and he replied, “Well, he probably won’t ask you both!”

  I spent a lot of time thinking about my outfit. I had this great Proenza Schouler dress that I had taken to Paris Fashion Week in 2012; it was a contender, but I had worn it for everything important I had done since. There were a few other dresses, but ultimately I didn’t want to worry about how to cross my legs, so I just wore regular old J.Crew from head to toe. I decided to go with my inner Diane Keaton—white collared shirt, gray sweater, red glasses. I wanted to look like someone you would want to have at a fun dinner party. I had tamed my hair per the good advice of my friend Michael Smith, whose response to hearing I had an interview was, “I’m SO proud of you! Make sure your hair isn’t too big!” I did my own makeup, which was minimal because I hate how I look in makeup. The people at Charlie Rose gave me a little antishine and bronzer, but that was about it. They also put my hair in a good order. (Coincidentally, one of my best friends from UVM, Sam, was producing the segment, which made me feel much more at ease.)

  The interview was about 75 minutes long and over before I knew it. As soon as the cameras were off, Charlie and I both checked our BlackBerries, which had been lighting
up like crazy—Secretary of Health and Human Services Kathleen Sebelius had announced her resignation while we were taping. (And thank God she did it during the interview and not before—I had memorized our health-care enrollment numbers but would not have known what to say about her; I thought she was announcing the following day so hadn’t prepared any talking points on it.)

  I was so fucking proud of myself. Seeing myself on TV was probably one of the things I was most scared of in the world, and I was so worried about being able to talk about my accomplishments and still come off as myself, rather than some weird, scripted version of me. I kept it together until we got outside, and then Clay and Joe, who had been watching on the monitor, made me celebrate. I decided to not be too critical and take their word for it. I had told the story of my time with Barack Obama, and I did it justice and enjoyed it.

  The day the interview aired, David wasn’t home, so I was able to watch it by myself, though I almost didn’t watch it at all—it took two glasses of wine to psych me up to turn on the TV. When I finally put it on, I watched the whole thing through my hands like it was a horror movie.

  But I didn’t need to; I thought I was awesome. I laughed (I was funny!), I cried (I did it!), I didn’t make a mockery of Charlie’s show or Obama’s presidency, and that’s all that mattered. The next day Gayle King called me a “badass mamba jamba” on CBS This Morning.