Less than 20 pages into her memoir about her career in politics, Alyssa Mastromonaco — former White House Deputy Chief of Staff to President Barack Obama — describes one of her favorite achievements: Getting a tampon dispenser installed in the West Wing bathroom. “If we were truly serious about running a diverse operation and bringing more women into politics,” she writes, “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.”
Mastromonaco’s new book, Who Thought This Was A Good Idea? And Other Questions You Should Have Answers to When You Work in the White House, is full of these types of anecdotes: Jokes on the surface, substance underneath. It is telling that the White House did not have such a basic accommodation for female staffers until Mastromonaco “made it [her] mission” to provide it; it is also hilarious to think of her standing in the Roosevelt Room, announcing to a meeting of mostly-male senior staff that the tampon dispenser would be installed that day.
After almost ten years of working for Obama, Mastromonaco left the White House; she’s currently an executive at A+E Networks and a contributing editor at Marie Claire. She spoke with ThinkProgress about encouraging women to work in politics even if it means grinding your teeth so hard in your sleep that your wisdom tooth shatters and you wake up with a mouthful of blood (for instance), what Obama was like as a boss, and her take on the Trump administration’s, shall we say, lax attitude toward traditional White House protocol.
I want to start where your book starts, which is with your legacy: The tampon dispenser in the West Wing bathroom. You write about how there wasn’t one when you really needed it, that you made it your mission to have one installed, and as soon as you brought it up, there was “no objection” to your idea. (And that you announced the installment of this dispenser during a senior staff meeting in the Roosevelt Room.) Why was it so important for you to include this story?
Well, the real lesson — and in the book, I went through the lessons I wanted to impart — was not that I’m a fucking genius, but that the reason it had probably never happened before is because no one thought to ask the question. The one thing Barack Obama always encouraged, and we always tried to do, was just ask questions. He was really the essence of ‘there are no stupid questions.’ So I wanted to put it in the beginning to show people: Just ask questions. And you might even get a tampon machine.
Were you always planning to lead with that anecdote? How did you decide where to place it in the narrative?
Originally when I was writing the book, it was a bit more chronological and I was like, this is boring. So I shifted it with some great advice from Mindy Kaling, who told me, “people want to read a story.” And I was like, what if we break it up by theme? So I sat down, made a list of the things that I thought about myself that were weak that became stronger, or that were always fairly present, and why, and why. So the list that I actually came up with, the original list, is the one that I used for the book.
“I tried to never say, ‘This is how Barack Obama felt.’ Because how the fuck do I really know? I never try to project my view on emotions people were having or feeling. I tried to keep it focused on me.”
As you say, the reason there was no tampon dispenser in the White House was simply because no one had thought about it. I’m curious how much institutional sexism you think is the result of that kind of lack of thought, as opposed to outright malice.
My view is, they don’t give it any thought. I don’t think it’s malice. But not considering an entire sex that needs tampons and maxi pads, it’s like, is not thinking about it some form of malice unto itself? For me, what I have learned is that nobody wants to talk about tampons and getting their period in the workplace. We talk about it, blog about it, tweet about it, but in the workplace, no one wants to talk about it. So I literally wanted to do nothing but talk about it.
The other day I was here at A+E, I didn’t have any tampons in my bag, and I went to the bathroom and we didn’t have them there either! I just walked into the bathroom and now we have a canister with that stuff in it. But is there anything worse?
You write at the beginning of the book that part of your goal here is to encourage women to work in politics, to provide a model you didn’t have. But you’re also very real and even graphic about the toll of that job on your person; at one point, you describe waking up with your mouth full of blood because you were so stressed out that you shattered a wisdom tooth grinding in your sleep. Do you think that the realities of campaign and White House life will scare people off that path?
Here’s the thing: If I had read a book like this one ten years ago and things started to happen to me like that, I wouldn’t have thought I was crazy. I would’ve been like, ‘okay, this is what happens. I should make it a point to go to bed more, and maybe I shouldn’t go out to drinks after work.’ Instead of feeling alone. So the whole point of the book was to be like, you’re not alone.
And look at me. I was a fucking hot mess, and it didn’t mean I couldn’t have an important job. You can still be funny and have an important job. It was meant to be like, we’re human. And people don’t even talk about it, but men have had strokes in the White House who are my age… So these are super-stressful jobs. But instead of pretending like it had no effect on me, I was like, ‘here is the effect it had on me.’ And know when to hold ‘em and know when to fold ‘em. Sometimes you can do it for ten years, sometimes you do three. For me, knowing when to leave was important, because I left on a high note and with wonderful memories without wearing out my batteries and becoming an asshole.
What went into choosing which anecdotes to include and which to leave out, especially when you were thinking about Obama? Did you run anything by him, like, “Is it okay if I want to tell the world you called me when my cat died”?
Here is how I tried, very surgically, to figure out which stories to use. I put them through a test which is, ‘is this my story or is this really someone else’s story to tell?’ So a lot of people, like my friends from the White House, would say, “you didn’t put this in,” but I’d say, “that’s [Dan] Pfeiffer’s story to tell.” So I tried to talk as much as possible about the things that impacted me directly, or that I did.
“I probably, even after writing this book, think more about what comes out of my mouth in a meeting than the men around the table. And I think it is because, look, if you are a woman and you’re marching, there are so many expectations on us, you feel like you can’t help but fail somewhere.”
I tried to never say, ‘This is how Barack Obama felt.’ Because how the fuck do I really know? I never try to project my view on emotions people were having or feeling. I tried to keep it focused on me, which is also hard, because you feel like a total narcissist. But in the end, the point was to be a positive, funny, read-in-a-day, upbeat book.
In the book, you share some of the best advice Obama gave you. Did he ever give you bad advice?
POTUS? No, he never gave me bad advice.
You started working for Obama in 2005?
I started the day he was sworn in as senator.
So when he went from being a senator to being the president, he’s still the same person, and you’re the same person, but the context is completely changed. What was that like?
I will say that he — we tried to remain, all of us, as real as we had been from the beginning, if that makes sense. So he probably saw me in a different light, because now I had these members of the military reporting to me. But I’ll never forget the first day we walked into the oval office when he was there, the day after Inauguration, and I was like, “Wow, this is weird.” And he just laughed. I think he very much just tried to keep us down to Earth. And Michelle and the girls keep him down to Earth.
But there are still formalities you want or need to observe, right, out of respect for the office?
Exactly. When we were in the senate office, it was always a transition. I call him Senator Obama and he’s like, “Why are you upset with me?” And I’m like, “I’m not upset with you.” And he’s like, “Then why are you calling me Senator?” And having to explain, “If I don’t do that, Ted Kennedy will think you have this insubordinate staff.” So inside the office, he wanted to be known as Barack. And when he became president-elect, we were in the Chicago office and we would stand up when he walked by, and he would be like, “STOP IT.” But we had to!
You describe in the book an experience like that, but the person in the position of power is you, and you send an email without realizing how it will read given the authority you recently acquired.
I was well into my position of power when I sent that shit email. Which, I still kind of don’t think I was wrong. It did forever change how I looked at it. I sent an email I thought everyone would basically ignore, which was self-esteem, which was the point POTUS made: Why did I think that sending this irate email would fall on deaf ears? And his point was, “Alyssa, your words have power.” And I was like, oh, I guess they do! For me, coming into my own and really realizing the position that I had, we all maybe downplayed it a little bit, because it’s a scary thing when you realize what your job is.
Speaking of scary things: I experienced the strongest second-hand anxiety reading about the work you needed to do during Hurricane Sandy. For all the moments in the book where a reader might think, this woman has the coolest job, that was a moment of: Thank God that was someone else’s job.
That was one of the greater teachable moments for me. I learned so much so fast, I realized my capacity. This is a sort of ludicrous analogy, but it was like when POTUS, in the first term, wanted to do health care, and everyone is like, “You could lose reelection because of this.” And he’s like, “I don’t care. I would rather be a one-term president and do what I believe than do nothing.” And that’s how I felt about Sandy: People are really suffering, I’ve just gotta go. I’ve got to do what I do is right. And if for some reason my judgment is totally off, it will be pointed out quickly. Sometimes you need the person to get things done.
And then when it was over, Bruce Springsteen talked to you on the phone.
I was SUCH A NERD on that call. I was so lame. Like, “okay, okay, bye, thanks!” I should have done more with that opportunity.
“The one thing Barack Obama always encouraged, and we always tried to do, was just ask questions. He was really the essence of ‘there are no stupid questions.’ So I wanted to put it in the beginning to show people: Just ask questions. And you might even get a tampon machine.”
It’s strange to think that you still get starstruck, since you spent so much time with one of the most famous people on the planet.
I knew Obama before he was as big a star. But for me, meeting your heroes is sometimes so sad — I was never the person who was always running up and trying to meet people, save for the Queen and David Beckham. Bruce to me is just like, so iconic. So when he called, [I knew] this is the one thing my dad is going to be excited about.
What’s it like to have your professional identity inextricably linked not just to another person but to an entire administration? How do you separate yourself from that when you leave the White House?
It’s hard! You go, and you’re there, and I think you don’t realize it the whole time you’re there until you’re ready to go and then you’re like, ‘shit, who the fuck am I?’ When I left, I was like: ‘Who am I? Nobody? What am I good at? What do I do?’ Because there’s no other job out there that’s similar. It wasn’t entirely just my identity being linked to him. It’s like the whole meshugas. I’d worked with these people — Jon Favreau and I worked together for 12 years before he left the White House. It wasn’t just leaving POTUS. It felt like leaving the whole family. My final day in the White House I was like, ‘this is the series finale of The Facts of Life. This is so sad.’ And it was really hard.
And then you’re in Washington, D.C. Everything you know that’s happening is happening down the street and you’re not a part of it. And that’s why I did get depressed. So it takes a little while. And the reason I wanted to tell that story is because, a lot of people feel that when they leave all kinds of jobs, and I think it’s natural. People should know that. You’re not a loser. You don’t necessarily need Xanax.
It seems like the latest wave in workplace advice for women is very heavy on “speak up more in meetings” and “don’t apologize so much,” and generally just encouraging women to behave the way men have behaved with impunity this whole time. But there are social — and professional — repercussions to that behavior. So what do you make of that, I don’t want to call it a trap, but that conundrum?
It is a conundrum. I think, if I use myself as an example, I probably, even after writing this book, think more about what comes out of my mouth in a meeting than the men around the table. And I think it is because, look, if you are a woman and you’re marching, there are so many expectations on us, you feel like you can’t help but fail somewhere. I would always say that people want to work in places where they see themselves, especially in leadership. It’s very important. So [when] so many of these industries have more women, it’ll stop being such a thing.
In a recent interview, you said that you “never like to oversubscribe to sexism.” What do you mean by that?
I try to not default to that — not saying it doesn’t happen, but if something happens, I don’t just say it’s sexism. I think about it for a hot second. What really just happened? Is this a dude who treats everyone like shit? Is it an equal-opportunity fuck-up? Or is it directed to me because I’m a woman? Are they talking down to me because I’m younger? I always try to have some critical thinking about why what’s happening is happening.
What was the election like for you? How does it feel to watch Trump in action?
It is devastating to my core. And it’s not because a Republican won. Because one of the things that I really feel I had great appreciation for was how wonderful and generous the Bush administration was to us. And even in 2012, as deputy chief, part of my job — in terms of the monitoring between the White House and political engagement and the campaign so you don’t violate any terms of the Hatch Act — was making sure that the Romney people began their security clearances in case they won. That’s what you fucking do. You don’t get to be petulant.
“If you look at how President Bush used Crawford, it was really just as a social aspect. It wasn’t like the whole visit took place there. It was like, ‘No, I love Angela Merkel and I want to watch her barbecue.’”
So part of what has hurt me to watch this is, I feel like when the Bush folks onboarded us, we took everything they said really seriously. I was director of scheduling and advance, and they had binders of templates and protocols, and we were like, thank God we have these. And I’m not sure we changed that many of them. And the Trump folks are just skeet shooting. Everything we did, they’re just shooting clay pigeons in the back. “If Obama touched it, we kill it!” Not from a political perspective, but function of the White House, we did function very well. So I think it’s a fucking shame.
In your book you describe a lot of the rules of the White House, which seem pretty complex and important, but now the Trump administration does not appear to follow most of them. So I’m wondering how many of those rules are really rules, and how much is just protocol, and if they’re more formalities than actual laws, what happens if someone doesn’t follow them?
Correct. There are a lot of things that are rules, or standard operating procedure. There are things that are protocols. And there are things that have just “always been.” So for example, how you use the Oval and the Cabinet Room? Are there rules? No. But there are practices that have always been in place, that are smart, so we adhere to them.
My mom, when she was trying to teach me manners, she would say, “It’s not about you, Alyssa. It’s about making other people feel comfortable.” That’s how I feel about protocols. So much about protocol is about the guests you welcome in the White House. So if you’re trying to impress a foreign leader and show them that you are really trying to demonstrate your strong relationship, you can take them to Camp David which is a really big fucking deal. There’s a working lunch meeting, only to be outdone by a dinner meeting, only to be outdone by a state dinner. All those things matter.
So if I’m a foreign leader, I don’t know what the fuck the structure of this means. [Following those rules] made negotiating with foreign dignitaries much easier, because there was just a standard operating procedure. For the most part, people knew what it meant when you were inviting them for an official visit or a state visit. And now he just has people over to Mar-a-Lago. And the difference is, if you look at how President Bush used Crawford, it was really just as a social aspect. It wasn’t like the whole visit took place there. It was like, “No, I love Angela Merkel and I want to watch her barbecue.”
What’s your media diet been like since the election? How are you managing all the news now that you’re out of the White House?
Between Election Day and a couple weeks ago, I was obsessed. I was checking Twitter all the time. And then I realized I spent a lot of time reading 35 versions of the same story. So now I try to watch the news in the morning — I watch CBS This Morning because I love Charlie, Gayle, and Norah — and throughout the day I have CNN or MSNBC on mute, mostly because I’ve found in the Trump administration, you can be at work all day, get in your Uber to go home at night, and understand that some of your rights have been taken away over the course of the day. I got a subscription to the New York Times and I try to thumb through all sections. We all have precious few hours in the day to devote to our betterment… so that’s how I do it.
On a scale from “this is the apocalypse, we’re all going to be living in The Handmaid’s Tale” to “still chanting hope in the streets,” how are you feeling about the country right now?
I am pretty hopeful. Because here’s what I think: I think that if we want to see negativity, that’s very easy to do right now. But I look at the women and how they have bonded together, and for the first time in maybe memory, it’s really like, all for one and one for all. I know that even with this book, almost all of the clothes that I’m wearing on my book tour were made by women in Brooklyn, Ace & Jig, because I want to support them… I have really pivoted into an everyday, try to feel like I’m doing something, to just really support women. The presale proceeds from my book are going to the Women’s March, because I’m like, those women got together and got ten actions done in 100 days, let me help them do 20 actions in the first 200 days. So I’m hopeful. I’m trying to see a little glass half-full. Or at least with some water in it.
One last question for you: I’ve seen a lot of stories lately about people fawning over Obama’s post-White House fashion. Do you think that he’s actually dressing a lot better, or are people just over-celebrating the fact that his jeans fit now?
I think people are just excited to see those sunglasses and that leather jacket. He looks good! He’s killing it.