Who Thought This Was a Good Idea?

And Other Questions You Should Have Answers to When You Work in the White House


By Alyssa Mastromonaco

With Lauren Oyler

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If your funny older sister were the former deputy chief of staff to President Barack Obama, her behind-the-scenes political memoir would look something like this . . .

Alyssa Mastromonaco worked for Barack Obama for almost a decade, and long before his run for president. From the then-senator’s early days in Congress to his years in the Oval Office, she made Hope and Change happen through blood, sweat, tears, and lots of briefing binders.

But for every historic occasion — meeting the queen at Buckingham Palace, bursting in on secret climate talks, or nailing a campaign speech in a hailstorm — there were dozens of less-than-perfect moments when it was up to Alyssa to save the day. Like the time she learned the hard way that there aren’t nearly enough bathrooms at the Vatican.

Full of hilarious, never-before-told stories, Who Thought This Was a Good Idea? is an intimate portrait of a president, a book about how to get stuff done, and the story of how one woman challenged, again and again, what a “White House official” is supposed to look like. Here Alyssa shares the strategies that made her successful in politics and beyond, including the importance of confidence, the value of not being a jerk, and why ultimately everything comes down to hard work (and always carrying a spare tampon).

Told in a smart, original voice and topped off with a couple of really good cat stories, Who Thought This Was a Good Idea? is a promising debut from a savvy political star.



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."


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.

Dey and I got dropped off outside Caribou Coffee and shuffled our way down Pennsylvania Avenue, both regretting the past three months; breakfast bagel sandwiches with extra meat had become the rule, not the exception. I was scared shitless. Between my physical discomfort and my anxiety, I was sort of a wreck.

We got to the gate by the Eisenhower Executive Office Building and presented our IDs, and the agent told us our meeting that day would not be in that building—instead, it would be in the West Wing. We tried to convince the guard he was wrong, but he wasn't. After we went through our security screening—eagerly handing over our IDs again and waddling through the magnetometers—we held hands all the way down the walkway, past Pebble Beach where the reporters do their stand-ups, and into West Reception. Marines opened the doors for us. We looked around and wondered if they thought we were someone else, but then we just kept walking. (Another good piece of advice is to look like you belong.)

West Reception is hard to process—it's like if the waiting room for your office were a museum. Heads of state, diplomats, celebrities, and activists all walk through it on their way to meetings in the West Wing or with the president. It was a week or so before Christmas, and all the holiday decorations were up. We chatted about the wreaths and the trees and the ornaments—they are always very beautiful—while we waited to see Josh Bolten, President Bush's chief of staff, who wanted to welcome us and see if we had any questions for him. Besides, like, "What now?"

After our meeting ended, Melissa Bennett, President Bush's director of scheduling, took us to the Oval Office. The door was open, but we were so nervous that we just stood at the threshold. We were being such tools, but we knew no other way to be. Finally, they coaxed us in.

The Oval Office was much brighter than on The West Wing, which was off-putting for a second; it almost looks more like a TV set than what you see on TV. (I would later learn that they keep it that way so reporters don't have to bring lights to shoot there.) The wallpaper is the best wallpaper you have ever seen; the artwork would be in a museum if it weren't in the White House; the desk is the president's desk. Yet everyone was so happy and friendly and kind to us. At some point, I realized I wasn't watching a TV show—this was going to be my life.


Leadership, or Born to Run Things

The bathroom situation in the West Wing is probably not what you would expect: Toilets do not exactly abound. For women, there was only one full restroom on the ground floor, plus a single toilet in the hall on the main floor and one on the third floor. You would often find yourself waiting in line. What's more, the bathroom you were waiting in line for was not some elegantly decorated powder room with a gilded mirror and a pink fainting sofa and fancy soaps and lotions selected by Nancy Reagan and Jackie Kennedy. Besides a little primping antechamber with a countertop and a mirror, it was your standard office bathroom—three stalls, some sinks, unflattering light, and that's it.

On top of this, there were no tampons. I didn't think this was a big deal when I started working in the West Wing in 2009, but it was a huge pain to get out of the White House once you were already on the grounds—there was no running across the street to CVS between meetings. To leave, you had to brave the lines of tourists stopping in the middle of the sidewalk to take photos, and to come back, you had to show your ID, input your special code, put your bag through the security scanner, go through the metal detector. Everyone was always too busy to go through this in the middle of the day. (This is also why we always ate at the Navy Mess, the cafeteria across from the Situation Room where the Navy serves breakfast and lunch every day.) If it was a true emergency, I would sometimes ask my assistant, Clay Dumas, to run to CVS, but I started doing it so often that I began to feel guilty about it. He was busy, too.

The White House was also not a scene where you could just bum a tampon from your girlfriends. Though this is changing, there are not a ton of women working in the West Wing, and many of those who are there have already gone through menopause—not many people traveled with a stash of Tampax. Those of us who did still get our periods developed an understanding with one another, and with our assistants, that it was cool to go through someone else's bag or drawer in search of a feminine hygiene product while she was out. Still, it was not uncommon to find yourself in a… code red.

To support one another through the gender imbalance in the West Wing, some of the senior staff women and Cabinet secretaries organized regular dinners where about 15 of us would get together, talk about issues, and drink some wine. Perhaps appropriately, I got my period on the day of one of these dinners.

That workday was extremely busy, and I exhausted my tampon supply with no chance to replenish. As the time to leave for dinner approached, I began to do some calculations in my head. They weren't good. I needed to change my tampon, soon. Before I left.

I began to panic. Neither Danielle nor any of the girls downstairs had anything that could help me. The toilet paper in the bathroom was not absorbent, so you couldn't do the thing where you roll it around your underwear to make a diaper. I decided I would have to run to CVS before the dinner started.

No luck. A meeting ran long, POTUS had a question I had to find the answer to—I don't know what happened, but I ran out of time. I hopped in my car and barely made it to the dinner—I was one of the younger women going, so I didn't want to be late.

I thought everything was going to be OK, but I was wrong. In the middle of the dinner, someone said something funny, and as I began to laugh, my hearty "Ha!" quickly turned to, "Oh my God, oh my God, no no no." It was then that I began to bleed through my pants—coincidentally, also my favorite pair at the time. Blue-and-white houndstooth capris from J.Crew.

Of all the women at the table, probably about four of us still got our periods, and I knew the others didn't have tampons because I'd already asked them. I decided to abandon my dinner. I leaned over to my friend Kathy Ruemmler (who was White House counsel) and told her what was happening. She escorted me out to my car, where I bled on the front seat as I made my getaway.

The next day, I made it my mission to get a tampon dispenser in the West Wing women's bathroom. If we were truly serious about running a diverse operation and bringing more women into politics, we should give the office a basic level of comfort for them. Even if you had to pay a quarter, it would be better than menstruating all over the Oval.

There was no objection to my proposal; it just seemed like no one had thought of it before. I went to the head of the office of management and administration, Katy Kale, and said, "Hey, we should put a tampon dispenser in the women's bathroom," and she said OK.

A couple of weeks later, I walked into the 8:30 AM senior staff meeting—populated by about 20 or 25 people, including a lot of men—in the Roosevelt Room. The Roosevelt Room is a stately conference space where FDR once kept an aquarium and several mounted fish; today, it's decorated in subtle beiges, with a painting of Teddy on a horse in Rough Riders gear and a little statue of a buffalo. It was there that I announced the West Wing would be installing a tampon dispenser in the women's restroom that day. No one said a word, but it felt really good.

I realize I promised you that I didn't want to focus on "my legacy" in this book, but since they didn't engrave the tampon dispenser with "Made possible by Alyssa Mastromonaco," I wanted to leave a record of it somewhere. There are times when you need to be a bull in a china shop to get something done, and I'm capable of that, but I usually don't enjoy it. For me, leadership has always been much more about rallying people around a project or cause than about being held up as the Boss.

But leadership is not all triumph and victory; if your ideas don't work out, being a strong leader can carry you through to better times. My first formative experience with being in charge was when I was elected junior class president in high school. Even with my nuanced, enlightened approach, I was not popular. I ran for the position because I wanted to take the lead on prom planning for our senior year. (Turns out you actually only needed to be on prom committee for that, but oh well.) We ended up using the song my best friend, Cara, and I wanted, "All I Want Is You" by U2, for our special prom anthem. (I don't know why you need one, but you do.) Our theme was Riches in the Night, which is a line from "All I Want Is You," so we thought we were extremely provocative and edgy.

It almost didn't happen. After I was elected, a rival classmate decided that my junior prom date, who had a white Bronco with an eight ball tinted into the back window, was inappropriate.

The eight ball implied—but did not necessarily confirm, given how much high school boys love bragging—that he was a drug dealer, and my rival launched an impeachment campaign against me weeks before the dance. The betrayal culminated in my class adviser interviewing me about why I was a good and worthy class president in the gym in front of all my classmates, who were sitting on the bleachers.

I was furious, but I had to push forward. Senior prom could not be lame!

The people voted, and I remained; one of the hallmarks of a great leader is being able to explain your decisions. When I was in college and Bill Clinton was going through his impeachment proceedings, I remember thinking that not everyone could speak with the same elegance and finesse that I had displayed during Eight-Ball Gate.

Senior year, I ran for band president. Not because I wanted the glory of being band president—though it was a very high-profile position—but because I wanted our senior band trip to be to New Orleans. My platform was solid; all the members of the band agreed that we should go to the competition in NOLA. But we ended up in Philadelphia. Maybe sometimes rallying support for your ideas isn't enough; maybe taking 40 teenagers to Bourbon Street will always be a hard sell to the principal. After I left, selection of the band president became an appointed position, no longer voted upon.

When I graduated from college, I got a job as a paralegal for the law firm Thacher Proffitt & Wood, which was located in the World Trade Center. Initially, I was not into this; I had wanted a job on Capitol Hill, but none of the (many) places I applied hired me, so I went to a headhunter in New York City who got me an interview with TPW. (And many other law firms, but none of them called me back.) I was disappointed, but I came around. It would be exciting to work in such a famous building—I liked the hustle-and-bustle vibe immediately. Also, TPW was the only firm that didn't ask for my GPA. My grades were fine—I had a three-point-something—but at the other firms it was like you had to be Phi Beta Kappa to Xerox closing documents.


  • "Always fascinating and very funny, Alyssa's book is full of juicy stories from one of the world's most glamorous jobs."—Mindy Kaling, New York Times bestselling author of Is Everyone Hanging Out Without Me? (And Other Concerns) and Why Not Me?

  • "WHO THOUGHT THIS WAS A GOOD IDEA? is everything we've come to know and love about Alyssa over the decade we worked with her: brilliant, funny, grounded, and inspiring. Anyone who's interested in politics - especially young people - should read this book."—Dan Pfeiffer and Jon Favreau, former communications director and speechwriter for President Barack Obama

  • "Few people have had as much access and influence over national events over the last decade as Alyssa Mastromonaco. No matter how serious the crisis or hard the problem, Alyssa took care of it with great skill and professionalism, and even greater humor. This book tells the story of a young woman succeeding under extraordinary circumstances, and throughout it all, never taking herself too seriously."—Stephanie Cutter, former deputy campaign manager for President Barack Obama

  • "I've often wondered how a woman can be so many things wrapped up in one dynamic package. Alyssa is my fairy godmother: she's wise, resourceful, insanely smart, and makes me laugh in a very special way. Her stories - from the front line of the White House to her kitchen - will entertain, inspire, and humor you for a long time to come."—Amanda de Cadenet

  • "Alyssa is a force: whip-smart, humble, and funny as hell. Her writing is as fearless as she is."—Sophia Amoruso, founder and CEO of Girlboss

  • "A candid and charming memoir of her unexpected career in government...The memoir abounds with intimate glimpses of Washington, D.C., celebrities (Biden, Clinton, Michelle Obama, and scores more) and cheerfully dispensed survival strategies. An entertaining look inside the White House."—Kirkus

  • "When imagining working in the White House, many picture meaningful meetings, glamorous dinners, and high-stakes decision making. It can be all of those things. But as Alyssa Mastromonaco writes in WHO THOUGHT THIS WAS A GOOD IDEA?, the reader gets a real and raw peek behind the curtains where Alyssa experiences the good, the bad, the distressing, and the often hilarious. Alyssa has real grit and grace, and her book is her story very well told."—Dana Perino, New York Times bestselling author of And the Good News Is... and Let Me Tell You About Jasper...

  • "A combination memoir and compendium of very good suggestions about how to get ahead -- very far ahead -- at an early age."—The Washington Post

  • "[WHO THOUGHT THIS WAS A GOOD IDEA] is brimming with...humorous, behind-the-scenes anecdotes, as well as up-close-and-personal moments with Obama that shed new light on who he is as a leader, man and friend."—People.com

  • "A moving, funny, and sometimes heart-wrenching look back at the years [Alyssa Mastromonaco] spent in politics and by [President Obama's] side."—PopSugar.com

  • "This relatable memoir is packed with juicy on-the-road stories and crisis management advice, and presents a strong case for embracing a sense of humor in the face of humbling setbacks."—Esquire.com

  • "Mastromonaco's memoir successfully avers that a tough, high-profile job is attainable and enjoyable for any woman who is as smart, ambitious, humble, silly, and hard-working as she is. Her book is full of enjoyable storytelling intended as encouragement for women of her generation and younger."—Publishers Weekly

  • "A must-read for anybody who's even remotely interested in how Washington works, but is worth reading for anyone who enjoys brilliant wit and once-in-a-lifetime stories...you'll probably end up reading it more than once."—Popsugar.com

On Sale
Mar 6, 2018
Page Count
272 pages

Alyssa Mastromonaco

About the Author

Alyssa Mastromonaco served as assistant to the president and director of scheduling and advance at the White House from 2009 to 2011 and as assistant to the president and deputy chief of staff for operations at the White House from 2011 to 2014. She is the New York Times bestselling author of Who Thought This Was a Good Idea? with Lauren Oyler and a contributor to Crooked Media.

Lauren Oyler is a writer whose work has appeared in the New York Times Magazine, the Baffler, the New Republic, VICE, and elsewhere.

Learn more about this author