Who Thought This Was a Good Idea?

by Alyssa Mastromonaco

  Copyright

  Copyright © 2017 by Alyssa Mastromonaco

  Cover design by Jarrod Taylor. Cover photograph by Pete Souza.

  Cover copyright © 2017 by Hachette Book Group, Inc.

  Hachette Book Group supports the right to free expression and the value of copyright. The purpose of copyright is to encourage writers and artists to produce the creative works that enrich our culture.

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  Twelve

  Hachette Book Group

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  twitter.com/twelvebooks

  First Edition: March 2017

  Twelve is an imprint of Grand Central Publishing. The Twelve name and logo are trademarks of Hachette Book Group, Inc.

  The publisher is not responsible for websites (or their content) that are not owned by the publisher.

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  Interior photos courtesy of the author.

  Library of Congress Cataloging-in-Publication Data has been applied for.

  ISBNs: 978-1-4555-8822-0 (hardcover), 978-1-4555-8821-3 (ebook)

  E3-20170218-JV-PC

  Contents

  Cover

  Title Page

  Copyright

  Dedication

  INTRODUCTION: You’re Probably Wondering How I Ended Up in This Situation

  CHAPTER 1: Leadership, or Born to Run Things

  CHAPTER 2: Preparedness, or The Patron Saint of Digestion

  A BRIEF INTERLUDE FOR SOME MORE PREPAREDNESS TIPS

  CHAPTER 3: Independence, or You Can’t Just Tagalong

  CHAPTER 4: Self-awareness, or Are You There, FEMA? It’s Me, Alyssa

  A BRIEF INTERLUDE ON HOW TO BE RESPONSIBLE WITH MONEY

  CHAPTER 5: Some Personal Shit You Should Probably Know

  CHAPTER 6: Confidence, or The Hope Flood

  CHAPTER 7: Humility, or Changes We Can Believe In, Sort Of, If We Have To

  CHAPTER 8: Risk-taking, or Ah-LEES-ah Goes to Brooklyn

  CHAPTER 9: Resilience, or A “Serious” Breakdown

  CHAPTER 10: Kindness, or A Spirit Soars over Denali

  CONCLUSION: Politics, Now with Less Navy

  Photos

  Acknowledgments

  About the Author

  Mission Statement

  Newsletters

  To Mummy, Poof, and Moosie

  For letting me be me since 1976

  INTRODUCTION

  You’re Probably Wondering How I Ended Up in This Situation

  When I first met Barack Obama in December 2004, I’m not sure he liked me very much. I had worked for John Kerry on and off for four years, and although the secretary of state has a reputation for being aloof, the two of us had had a very warm and close relationship, pretty much from the moment I started as an assistant in his press and scheduling office in the spring of 2000. I expected my rapport with Senator-elect Obama, who was much closer to me in age and disposition, would be similar. Plus, I was coming off the presidential campaign for the Democratic nominee. I figured Obama, who was basically unknown at the time, would be thrilled that someone with so much experience—as well as so much wit and charm and talent!—would want to come and work for him.

  I was wrong; Barack Obama is tougher than that. He cared less about my credentials and more about the fact that I wasn’t from Illinois. He wanted someone with a connection to his constituency, which I didn’t have. I think he also wanted someone who wasn’t too big for her britches, and he couldn’t tell immediately how I fit into my britches. Literally or figuratively—the stress of a presidential campaign is not kind to the waistline.

  But I really wanted to work for Obama. After the brutal Kerry defeat, I especially wanted to work for someone who was not going to run for president—I didn’t think I could take that heartbreak twice in a lifetime—but I also thought Obama was no bullshit and so, so smart. Even then it was clear he was special.

  I’d heard about the position from my friend Robert Gibbs, who had quit the Kerry campaign to work on Obama’s US Senate race. One day after we lost, I was in the Kerry office, doing the very solitary, depressing work of making sure everyone’s invoices had been paid before we turned the lights off for good, when a message from Gibbs popped up on my AIM: “What are you doing now?”

  I said I was wrapping things up, and after that, I didn’t really know.

  “Do you need a job?”

  Yes, I did. I had been thinking about going on to work for John Kerry’s PAC, but it wasn’t clear I’d get the role I wanted, deputy PAC director. Gibbs told me he was working for Barack Obama, who was really great, and that he thought I should interview to be his director of scheduling—a senior adviser. Pete Rouse, a famous and beloved figure on Capitol Hill, had just signed on as chief of staff.

  I told Gibbs I would look into it, and soon after, I met with Pete (who was wearing cowboy boots and jeans). He liked me and set me up to meet Obama.

  Walking into the interview, I wasn’t nervous, really. If you’re nervous, you seem uncertain, and I’ve always gone into interviews with the sense that, if it works out, that’s great; if it doesn’t, then it wasn’t meant to be. Besides, Obama was wearing a black mock turtleneck—it put me at ease.

  It was a fairly run-of-the-mill interview, with Obama at the head of the table and me across from Pete and Gibbs, going over my life and my priorities. Why would I want to work for him when I wasn’t from Illinois? And since I had just come from doing what was essentially a much more intense version of the same job—with a very big staff and a lot to do—wouldn’t I get bored sitting around at the Senate all day?

  I didn’t feel like I’d nailed it. Obama bid me farewell with a classic job interview move: “We’ll be in touch.” But if nothing else, I felt confident in my personality—at worst, I am “good but difficult” (and a tad sensitive), and at best I am assertive but laid-back, resilient with a righteous sense of humor. Even if I don’t manage to get people to like me, I can usually persuade them that I am competent and not (too) annoying.

  And that’s how this story starts—with the humble goal of seeming competent and not too annoying. Like most women I know, I ultimately want to be likable and trustworthy—as well as glamorous—but it’s important to take baby steps. Though Pete later told me it had taken some persuading, Obama called and offered me the job.

  I wrote a lot of this book during the 2016 Rio Olympics, and even though social media was around for 2012 and 2008, this year’s Games really felt like they were taking place online. If I didn’t catch an event when it was on TV, it was pretty easy to figure out what had happened by looking on Twitter. And on Twitter, the commentary was much funnier.

  One of the most iconic images from this Olympics was quickly turned into a viral meme by someone with 830 followers named @a7xweeman. The photo is really crazy: In the semifinal for the men’s 100-meter dash, the Jamaican sprinter Usain Bolt, the fastest man in the world, is looking over his left shoulder as he pulls away from the blurry mass of his competitors, all of whom are pretty far behind him, and he is smiling. Huge. @a7xweeman’s caption for this picture was, *Record scratch* *Freeze frame* Yup, that’s me. You’re probably wondering how I ended up in this situation.


  I am 5 feet 2 inches and not a sprinter, or a runner, or an athlete; I switched to Pilates in 2006, after I nearly broke my teeth falling off a treadmill. (I was BlackBerrying.) Nevertheless, I’ve often felt like this during my career: “Yup, that’s me. You’re probably wondering how I ended up in this situation.” When you see my life on paper, it’s not remotely obvious how I would end up, at age 32, working as the right-hand woman to the first African American president, sitting across from him on Air Force One heading to Afghanistan, Russia, China—or, honestly, anywhere.

  As I write this, I am 40 years old, not even close to the end of my career, and I’ve already done more than I ever could have imagined for myself. I am a townie from Rhinebeck, New York; now, it’s a posh little weekend-getaway spot that appears in hashtags and cooking shows, but when my family and I moved there it had one stoplight, our road wasn’t paved, and the “chicken in a pita” at Del’s Dairy Creme was the pioneering predecessor of the artisanal farm-to-table movement. I graduated from high school with about 76 other kids. I was a good(-ish) student, but I was also a big fish in a small pond. My wardrobe consisted of flannels and Grateful Dead T-shirts, and my biggest accomplishment was surviving an impeachment as student body president, followed by my mean impression of Eddie Vedder. When I got a job as a checkout girl at Kilmer’s IGA Market, I was the fastest and most fastidious checker on double coupon day (do not try to pass off an expired coupon on me). I loved working the Wednesday before Thanksgiving because it put my bag-packing skills to the ultimate test.

  A lot of people ask me how a public school kid from Upstate New York with no connections and no Ivy League acceptance letters, who spent more time at God Street Wine shows than in academic club meetings, ended up a few feet from the Oval Office, working as one of the youngest women ever to be a deputy chief of staff for the president of the United States. Sometimes these people are being rude, like, How could someone like you end up in a job like that? Sometimes they’re genuinely curious. Sometimes they want to know so they can do it, too.

  I wanted to write this book to try to answer the question for everyone, but especially the last group. (The jerks are least important to me, but they can still eat it.) I have come to believe that hard work and a good attitude can get you further than you could ever dream, and unfortunately, this is a really basic lesson that doesn’t come up in most career advice. It’s kind of cheesy, but sometimes life is cheesy for a reason.

  I also wanted to write this book because I didn’t see anything like it out there. When I was trying, kind of desperately, to get a job in politics, and then when I got one, all my mentors were men. Most political memoirs are written by men—because most of the people who work in politics are men—and they’re usually preoccupied with legacy: reliving the glory days, dispensing tidbits of “insider” drama, and making the writer look like he has single-handedly triumphed over adversity and evil Democrats. (Or evil Republicans—trying to make yourself look good is a nonpartisan issue.) I understand wanting to leave a legacy, but I’ve always tried to focus on the work first, usually knowing—except in dark moments—that my glory will come in time.

  At this point, you might be feeling like, “Who is this lady and why should I care?” Fair. If you Google around, you will find me, but I’m not a household name. I was once on a list of Washington’s most powerful, least famous people. A lot of jobs in politics are basically about getting shit done, and I have had a few of them. They’re not as sexy as being an actual politician, but most people—including me, for example, hi—don’t have the constitution to be an actual politician. The jobs are still very important, and cool, and kind of unbelievable, as the number of state dinner bloopers I recap in this book will demonstrate.

  At the end of the day, I hope you can learn from all this, including the stomach problems. I’m not interested in speaking from a place of superiority; I learn things from young and inexperienced people all the time, and I’ve been young and inexperienced myself. I know what it’s like to be treated like you rank somewhere between a baby and a run-of-the-mill moron. I have also acted like a baby and a moron at a few points, even though I am neither. I don’t expect you to know who God Street Wine is—it’s a jam band that broke up, sadly, in 1999—but I think my story can make you all feel less alone, less weird, less anxious, and more confident. It all turns out OK.

  One day in late October 2008, almost four years after I started working for Obama and just days before the general election, I woke up to see a forecast of snow for Chester, Pennsylvania. A panic spread throughout the campaign headquarters, and especially through the scheduling and advance department, where I was working as director. Senator Obama was slated to do an outdoor event in town later that morning, and we were all waiting to see which of us would get the dreaded email. It would come from Marvin Nicholson (Obama’s trip director, and my former boyfriend of six years), Reggie Love (Obama’s body person), or Gibbs (Obama’s press secretary); together, they made up what we lovingly called the Road Show because they traveled with Obama everywhere he went. Sometimes, disagreements would arise between the Road Show and HQ, and duking it out with your team is never fun. In HQ we occasionally had ideas that were a little campy or aggressive, but we weren’t the ones who had to answer to Obama’s disappointed face when he turned to them and said, “Uh, who thought this was a good idea?”

  Shortly after that happened, I would usually get an email from Marv or Reg or Gibbs relaying the question. They would know full well it was me, but it was a gentle—or passive-aggressive—way of calling me out.

  Anyway, Chester, PA, 2008. The forecast was bleak, and Senator John McCain was canceling his events.

  I had been working with Senator Obama long enough to know that he was not fond of the cold. (He still isn’t—I mean, he’s from Hawaii.) But how better to show contrast with an old and tired Senator McCain than with a spry and virile Barack Obama, so dedicated to the American public that he would endure a snowstorm to tell them about his vision for the country? Talk about leaving it all on the field! I was really into this idea. He had to keep Chester on the schedule.

  I went to Plouffe—as in David, the campaign manager—and laid out the facts. There was no question about it, I told him: We were keeping Chester as is. He completely agreed. Outside, in the snow, Kenny “Town Hall” Thompson—one of our best advance leads, who was especially skilled at pulling off the greatest town hall meetings in politics—was about to execute what would become one of his most famous events, and we were not going to miss out on this opportunity because of a little precipitation.

  I sent the decision to Road Show and to the advance team in Chester, who were in charge of developing and executing the event. A few minutes later, the cringeworthy but expected response from Reggie was in my in-box: “Alyssa, who thinks this is a good idea?”

  We all did, but that didn’t matter. As the director of scheduling and advance, I had to respond that it was my idea. It was my responsibility.

  About two hours later, the event began, and we watched it on TV from the headquarters in Chicago. As our boss began to attempt a speech that would convince Pennsylvania citizens to get out and vote for him, we noticed something terrible.

  “It’s sideways sleeting!” Dey cried. (Dey, aka Danielle Crutchfield, was my deputy and suffered the same email traffic I did when things didn’t go according to plan.)

  Barack Obama was on TV being smacked in the face by sleet. So much worse than snow. Basically worst-case scenario.

  We watched (in horror) as the event drew to a close, and Obama reached his hand to Reggie. As we were turning off the TV, my phone rang.

  “Alyssa, it’s Obama.”

  “Hi!” I said, with my head down on the desk, girding myself for the inevitable and deserved. “The event looked AWESOME! You heard John McCain canceled all of his events, right? He looked like a total old man!”

  “Alyssa, where are you right now?”

  I was not sure where he was going with
this, but I knew it was somewhere bad. “My desk,” I replied cautiously.

  “Must be nice.”

  Click.

  The choice to keep Chester on the schedule—my decision—was always going to result in some version of that conversation. But we all knew that slowing down in the last week of October was not an option. Besides, Obama does not hold a grudge—by the time we saw each other on Election Day this would be the last thing on his mind.

  You should always be prepared to defend your choices, whether just to yourself (sometimes this is the hardest) or to your coworkers, your friends, or your family. The quickest way for people to lose confidence in your ability to ever make a decision is for you to pass the buck, shrug your shoulders, or otherwise wuss out. Learning how to become a decision maker, and how you ultimately justify your choices, can define who you are.

  This decision was not dissimilar to what happened when I put Sun-In in my hair at seventh-grade field day even though my mom specifically told me not to: painful at first, but it worked out in the long run. The Chester fiasco was notable for more than just our drama. A week and change later, we had won the general election, carrying the District of Columbia and 28 states, including Pennsylvania. The next year, Damon Winter, a photographer from the New York Times, received a Pulitzer Prize for his coverage of the campaign, and the winning work included a photo he took of the event. Though the soon-to-be POTUS teased me for it for a little while afterward, Winter’s award vindicated how everyone felt that day—including Obama. It became one of our favorite moments. The sleet pelting him in the face was front and center. And my hair is blond to this day.

  I first walked through the gates of the White House about a month before Obama took office and I would officially start working there. I was going to be the assistant to the president for scheduling and advance—basically the same thing I had been doing, but like 50 times more complicated. Assistant to the president is the most coveted position in the White House; there are only about 20 to 25 of them at any one time. I was one of the youngest women to ever hold that title, if not the youngest.