Who Thought This Was a Good Idea?

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Who Thought This Was a Good Idea? Page 18

by Alyssa Mastromonaco


  I, however, sat down and did what I thought was thoughtful and considered math: I incorporated what I could expect to bring in through fees for speaking events, what I had made working in the government, my experience level, and what other companies had floated as salaries to me when I met with them. I came up with a number, and I sent it to VICE.

  I’ll say it again: Don’t do this!!!!! When they came back with less than what I’d asked for, instead of chalking it up to negotiation tactics and calling Bob, I was shocked. All my bros from the White House didn’t seem to run into this issue when they got their first jobs post–White House; as far as I knew, they’d just gotten their offers and accepted. (This is probably not what happened.) At the time, I don’t think I realized my confidence was still simmering on low. Maybe I wasn’t who I thought I was? I talked them up a bit and accepted the job.

  Two months later, I showed up for my first day—January 5, 2015—and it was immediately clear that I was in for a culture shock. VICE is, as Shane Smith told the New York Times for the article that ran about my move, “craz[y]” and “freaky”—a huge place with hundreds of people. Many have tattoos, fewer are skateboarders; there were a lot of ripped jeans and very purposeful hairstyles. Some crop tops, even in January. The office sees a huge turnover of business-looking people, as well as celebrities, every day; no one cared—or even noticed—when I walked into the cavernous space on North 11th Street where the Brooklyn office was located at the time. Most people were typing intensely on MacBooks, not looking up or talking, even though they were all sitting at communal tables. It would take me maybe longer than it should have to realize that they weren’t cold or rude—they were just concentrating on writing.

  After a week or so, I was able to make some observations: (1) This was the first time ever that I had been the oldest person in the room. (2) This was the first time in maybe 12 years that I had been “the new person”; I even had to ask where the bathroom was. (3) I basically knew nothing about how media companies operate. (4) This was going to be much harder than I had expected.

  Trying to write a book reflecting on the successes and lessons of your career is very hard when you genuinely feel like a fraud who hasn’t learned from any of her past mistakes. In my experience, it is, in fact, impossible.

  Months passed, and almost every day I thought about the book. I had convinced David to move to New York with promises of how fun our life would be there, but the transition was a total disaster: The sale of our Georgetown place fell through at the last minute. We bought a condo in Tribeca only to learn that construction was a year behind schedule; we had to live in short-term rentals until it was finished. The first place I found online—on Greene Street in SoHo—turned out to be a scam: I went on StreetEasy and saw that the building was owned by someone who was not the person I had been communicating with, and I had already paid a deposit and the first month’s rent. One of the places we ended up staying in Williamsburg had pleather couches. Often, the apartments were in crappy new buildings where recent college graduates—who, famously, like to party—lived. At one point during this saga, when it was particularly chaotic, David said to me, “I did not achieve in my life to live with twenty-two-year-olds.” I had failed at leaving the White House and had no one to blame but myself.

  At least a few times a week I would open up my computer—the one David bought me when I got the book deal—and stare at it. Every morning at 5:30 AM an Outlook reminder went off, telling me to get up and write my book. I would get out of bed and sit on a pleather couch and not write it.

  I convinced myself that I just needed to feel settled—to be “home”—and the words would come. But when we finally moved into our place in Tribeca—our home—they didn’t. I challenged myself to dedicate all day to the book every Sunday, and I would go down the street to Kaffe 1668 and sit and write. After nine Sundays dedicated to this, I had two tiny chapters.

  By April 2016—almost two years since I’d gotten the deal—I had pretty much decided to give up. I just hadn’t told anyone else.

  In the months leading up to this moment, VICE had been in collective bargaining contract negotiations. The August before, the editorial team had voted to unionize, and I had been put in charge of the negotiation process for the management side, which is kind of hilarious and horrible when you think about it—a lifelong active Democrat negotiating against the worker. (I guess the flip-side rationale was that I was familiar with labor unions.) This was hard for me to resolve, especially because I was someone who was relatively new to a company full of fiercely loyal employees; they didn’t know me, or have a reason to trust me, at all. I hit an emotional rock bottom. The night after a particularly brutal, hours-long bargaining session, I was drinking wine on the floor of my bathroom. My cat has severe anxiety, and he wouldn’t come out, so I just stayed in there.

  I began suffering from debilitating stomach pains, and after two trips to urgent care and a week of freaking out on WebMD, I went to a doctor.

  He asked a hundred questions about my life—eating habits, family history, sleep patterns. One of the last ones was, “Do you drink alcohol?” I said yes.

  “How is that possible?” he asked. “It must kill your stomach.”

  “It’s actually the only thing that makes me feel better,” I said.

  Aha. He went straight for the jugular. He asked about my job, and I melted into tears right there in my hospital gown. Not heaving, sobbing tears, but the tears actresses aim for in movies. Streaming out of the corners of my eyes. His theory was that my intense stomach pains weren’t the result of giardia from Mexican takeout (my WebMD diagnosis) or IBS or cancer (other WebMD diagnoses) but from anxiety and depression.

  I couldn’t believe it. I would never look in the mirror and think I was seeing someone depressed. And anxiety? After six and a half years in the White House, working in media was giving me anxiety?

  The doctor and I talked about how the White House was probably exhausting, and difficult, but in a way, shockingly, controlled for me. I was used to that kind of environment because I am a planner, but much of what happens in media evades planning—you never know when a story will break, or when someone will have a great idea that a team needs to start working on now. The theory was that the chaos at VICE and my inability to wrangle it were literally destroying my insides. (This doctor is a gastroenterologist and not a therapist, just to be clear, but I would support his taking up a side gig if the stomach stuff doesn’t work out.)

  He gave me a prescription for Zoloft. I didn’t really want to take medication, but I needed something, and within 48 hours my stomach pains were gone. I felt like an entirely new person.

  The union negotiations wrapped up shortly after I told myself that I would abandon the book, and despite feeling dejected that I was on the verge of giving up on this project, the vibe around the office got much lighter. (The editorial team all got big raises, among other things.) I didn’t feel like everyone hated me anymore; in fact, I started to make some friends.

  One of the good things about the process was that it allowed me to get to know a handful of employees much better. Lauren Oyler represented the women’s vertical site, Broadly, at the bargaining table, and I had read what she’d been writing for months. Her arguments were always compelling, and she was always working; I began to think she might be able to help me with the book. I needed structure and perspective pretty desperately. Also, given the target audience, I really wanted a millennial POV.

  A little more than a month after negotiations ended, we worked together on something else, and I got to know her more. She was smart and no bullshit and just straight-up impressive. I identified her as my savior.

  It was July at this point, and I was at a shit-or-get-off-the-pot moment with this damn book.

  Since her name is on the book, you know how this ends. She helped me focus, gave me direction, was critical but kind, and most importantly reminded me why doing this mattered. She also assuaged my fears that this was a self-aggra
ndizing I’m the Best and Only Champion of Politics type of memoir.

  One of the good things about being resilient is that, when you’re forced to veer off course, you pick up skills you didn’t realize you needed. That was probably the most I’ve ever struggled professionally, but I’m still here. Being resilient means being honest: You have to admit when you’re struggling. Usually, someone will help you.

  (Hi, it’s me, Lauren, writing to you from my kitchen table in Brooklyn. I feel strange letting a string of compliments about me into the book, but there needs to be a resolution to this story, and I am, weirdly or not, the resolution! If you would like to know my personal favorite part of the book, it’s when Obama walks in on Alyssa doing sit-ups in her office during a Senate Voterama and goes, “Good for you.”)

  CHAPTER 10

  Kindness, or A Spirit Soars over Denali

  When I was 18 and working at Kilmer’s IGA in Rhinebeck, I took an afternoon shift on prom day. Most of the other checkers were off getting ready, but I agreed to work the latest shift because my hair was really short and I wasn’t having it done. I was about to close out my register when Natalie Merchant, the lead singer of 10,000 Maniacs, and Michael Stipe, from R.E.M., walked in.

  Natalie lived down the road, in Rhinecliff, and she came to Kilmer’s often; she was probably the first person I ever saw use recyclable grocery bags. She was very friendly and asked where all the other girls were. I told her it was prom night and that as soon as I rang her up, I was going to leave and put my dress on, too. (It was a very plain little black dress—a real departure from the bugle beads and sequins I had worn the year before.) She asked where the dance was, and I told her.

  About five hours later, slow dances to All-4-One’s “I Swear” at Valeur Mansion on River Road screeched to a halt and we were treated to an impromptu performance by Natalie Merchant, who stopped by to say hello. She welcomed all the girls who were in the choir to join her. This was long before social media gave people instant credit for acts of goodwill—she just did it because she was a member of the community and thought it might mean something to us.

  It did. For one, because she was a notoriously private person—when you saw her in town, you didn’t fawn over her or ask for an autograph—but also because she didn’t stop by because we were the kids of important or famous people. We were the kids who scooped her ice cream and packed her grocery bags.

  There are certain lessons you pick up gradually as you go, letting them accumulate after a series of similar mistakes or experiences until you finally realize you’ve been a fool all along. And then there are the lessons that are so massive they smack you in the face—you don’t reflect on a period of your life and realize, “Oh, I learned something then”; you know it’s happening when it’s happening. The importance of kindness—which extends far beyond “please,” “thank you,” and “your hair doesn’t look bad today”—is a combination of both: Over and over in my life, I’ve been bowled over by how kind people can be, and how that kindness can change your outlook. Politics is often associated with secret dealings, competition, and corruption—and those associations aren’t necessarily wrong—but, fundamentally, it’s also about people and personalities. Working at the White House is obviously heady, but it’s also humbling—you’re around the most brilliant, decorated brains in the country. They don’t have to do anything for you, but they often do. If you approach it with grace—and a willingness to accept that many people know much more than you—you can walk away a much better person than you were when you came in.

  When we were kicking off the transition, I made a trip to DC for a meeting with President-elect Obama, and while I was waiting for him to meet me Larry Summers, who was about to become the director of the National Economic Council, zoomed by. I had never met Larry, but before becoming part of the Obama family, he was chief economist at the World Bank and treasury secretary in the Clinton administration, so I knew who he was and felt a little starstruck. It was one of many nerdy celebrity sightings at the transition office. As he was about to turn a corner, he whirled around and asked me to get him a Diet Coke.

  Just like that, my admiration turned to contempt. The gall! The nerve! The bad man! I was so offended. Did he not know who I was?

  Well, no, he didn’t. I was no one. While I had been cranking hard for years for Barack Obama and at times felt like a political veteran, I was 32 years old and looked my age only on a good day. I had packed on the pounds in Chicago, eating my fill of chicken al’ diavolo and chocolate cake from Portillo’s, and my cheeks were nice and full—it’s entirely possible I was clocking in at around 25. If I didn’t look like an intern, I certainly looked like someone who could get you a Diet Coke. Also, I was the only other person in the room.

  None of this registered at the time—I was indignant at what I perceived to be a sexist injustice against me. Would he ask a man to get him a soda? I begrudgingly got him a Diet Coke from the vending machine and decided to write him off forever as a douche bag. I committed to rolling my eyes (internally) every time he spoke.

  Months later, we saw each other again—in a meeting in the Roosevelt Room about the economic crisis. Larry was the president’s national economic adviser. Tim Geithner (secretary of the treasury), Christie Romer (chief of the Council of Economic Advisers), and Peter Orszag (director of the Office of Budget and Management) were sitting at my end of the table, along with Gibbs. The economists were talking about their alma maters (Dartmouth, William & Mary, MIT, Princeton), and Peter asked if Gibbs or I ever felt out of place because we didn’t go to an Ivy League school. I could feel my face getting hot—remembering that awful day when I got skinny envelopes from Cornell, Brown, and Georgetown saying “Thanks, but no thanks.”

  “Well, we all ended up at the same table, didn’t we?” Gibbs—who went to North Carolina State—shot back. “Seems like we got a bargain!” Um, true.

  Meetings on the economic crisis—of which there were many in 2009—made me so nervous, but as a member of the president’s senior staff I needed to understand what was happening, because recovery was POTUS’s number one priority. Everything POTUS did—his meetings, his events, the layout of his day—was viewed through the lens of “What can we do to impact the recovery?”

  These meetings were totally outside my comfort zone (I got a B–in Econ 101). I would always panic that one day POTUS would launch into the Socratic method and randomly ask me to pontificate on TARP (I will save you the Googling: Troubled Asset Relief Program) or quantitative easing (go ahead and Google this one—it’s good for you). I would break into a literal sweat just walking into the room.

  Because it was my responsibility to learn everything I possibly could, when people used a term I didn’t know the meaning of I would write it down to research, quietly and without embarrassing myself, later. During this particular meeting, I was sitting next to Larry, and I guess he saw my list of terms to search and articles to read; this time, it was focused on the shadow banking system, debt deflation, and subprime loans.

  In the middle of the meeting, he whispered, “Come up to my office after this.”

  The jig was up. He knew I was a fraud. Or worse—just not that smart.

  After the meeting, I followed him upstairs, where he asked about my list. As embarrassing as it was, I decided to just be honest and tell him. I was a moron! It was about to be all out in the open. Could I get him another Diet Coke?

  But to my surprise—since I’d labeled him a jerk—he was totally nice. “Well, if you knew everything I knew,” he asked, “what good would I be?” He took about an hour to explain very complicated concepts to me, and he suggested some articles that would help me get up to speed.

  I’m sure he doesn’t remember doing it, because he wasn’t trying to be extraordinary—he was just being kind. But because of that one gesture, I would always ask Larry questions when I had them, and when, as part of my job as deputy chief four years later, I had to screen candidates for chairman of the Federal Reserve, I w
asn’t a total disaster. When I sat with POTUS to do the interviews—Larry himself withdrew from the final round—I held my own, and I didn’t sweat through my dress worrying I might get caught up in a conversation I knew nothing about.

  Larry taught me two very important lessons. The first: Never judge a book by its cover (or the articles written about it). The second: Always make time to help a gal out. Kindness—you can call it generosity, or goodwill—really means something.

  Right after Hurricane Katrina in 2005, the Washington Post ran a story about how all the dogs that had been rescued from the storm were being adopted, but the cats were being euthanized. It featured a picture of this giant calico Persian named Tommy who had been evacuated from New Orleans and found his way up to the Persian Rescue of Virginia. I had always wanted to get a cat, and I felt like this was my moment.

  I called the rescuer, Margaret, and asked about Tommy. I said I was interested in him; she told me that he took up the space of four cats and that if someone didn’t take him this week he would probably be put down.

  The rescue was only about a 50-minute drive away, but I was afraid to go to the hinterlands of Virginia by myself, so I asked my friend David Wade to come with me. I figured Margaret had to be joking about how big he was. I mean, four cats?

  It was the weirdest experience ever. Margaret ran the rescue out of her condo, though it was clean and she clearly cared for all the cats very well. She brought Tommy to the kitchen and put him on the table. He yawned, stretched out to cover basically the entire thing, and closed his eyes but didn’t fall asleep—it was like he was meditating. Margaret had an Irish brogue and told us Tommy could sense when she was about to get her period. We asked no more questions. He was handsome and calm and I knew we were meant to be.

  Margaret put Tommy in a dog crate (he weighed 23 pounds—the size of three small cats), and Wade and I put him in the back of my Saab and drove back to the Hill. The entire ride back, Wade was in the front seat whispering “You’re free!” to Tommy.

 

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