When You Cry in the White House: A Frank Conversation with Alyssa Mastromonaco

In her foundational feminist text Of Woman Born, Adrienne Rich writes, “I believe increasingly that only the willingness to share private and sometimes painful experience can enable women to create a collective description of the world which will truly be ours.” This is Alyssa Mastromonaco’s ethos: the radical sharing of experience, in order to reclaim the world.

In her new book, So Here’s the ThingNotes on Growing Up, Getting Older, and Trusting Your Gut (co-written with Lauren Oyler), the former White House Deputy Chief of Staff for Operations under the Obama administration writes about these private and painful experiences in detail—such as IBS, not knowing if she wants kids, and almost causing an international incident with her toes. And she does it all in a voice that is breezy and fun, but not devoid of bite. Her honesty is raw and seeks to illuminate the darker corners of what it’s like to be a woman, from menstruating on motorcycles in Japan, to simply existing on Twitter.

But Mastromonaco’s words also come with a warning—much like Rich’s did. “On the other hand,” Rich warns, ”I am keenly aware that any writer has a certain false and arbitrary power. It is her version, after all, that the reader is reading at this moment.” This, too, is Mastromonaco’s caution, and the inspiration for the caveat and title So Here’s the Thing…, which she includes as a preface to all her advice and writing. “This book,” Mastromonaco writes, “is an attempt at a conversation, not a statement.”

Whatever that conversation is, whether in person or in writing, having it with Mastromonaco is a true delight. Recently, I spoke with Mastromonaco about for The Riveter about her book, autonomy, and the best places to cry in the White House.


Your book is full of great advice. It reminded me of this Adrienne Rich quote: “Only the willingness to share private and sometimes painful experience can enable women to create a collective description of the world which will truly be ours.”

Oh gosh, yes, I feel so seen. I always felt a bit like a weirdo growing up. I never really fit in. And I did have these weird health problems that no one ever wanted to talk about and that were so embarrassing. And the truth is, since I wrote the first book, [Who Thought This Was a Good Idea?], and talked about IBS, you have no idea how many women, some men, mostly women, have been like, “You’ve changed my life. I told my boss that I suffer from IBS, so if I feel like I need to get up and out of a meeting, I just look at her and she understands and it’s not a thing, and I don’t have to sit there and be anxious.”

I think the humor of the book, too, gives people a vehicle to be able to talk about it.

Right. Because it’s supposed to make it not embarrassing, like, “Oh, this woman in the White House talks about poop with Obama. I can do it, too.” Have you gotten a similar reaction to your discussion of motherhood, which you address in the book?

My age bracket—I’m 43—we missed the sort of egg freezing revolution. I had someone who was my age maybe two years ago say, “Oh, my doctor told me to freeze my eggs,” and I was like, “911. Get a second opinion.” Because over a certain age, your eggs just aren’t great quality anymore, so make sure you’re not being scammed out of terror. Where you’re panicking and your doctor’s like, “Oh, go freeze those eggs.” And then meanwhile, it’s like freezing rotten teeth. It could be. And it may not be, but it could be. And you know, I was talking about the fleecing of the middle-aged woman.

Look, I’m not someone who was like, “I’m going to get ahead and I’m putting kids on the shelf.” It all just kind of ended up where we ended up. And I don’t know. Who knows? I could end up adopting a kid in three years. Who fucking knows. [But] more than anything, what I hear from women is, “Oh my God. No one has ever just said ‘I don’t know’ before. No one said that it’s okay to not know and it doesn’t make you not sympathetic or not maternal.”

Do you ever feel conflicted about writing about motherhood?

This was the hardest chapter to write in the entire book. Because I wanted to be clear that this was how I felt, and I didn’t want to impugn or indict anybody’s decisions or non-decisions and have people be like, “Oh, well she’s just a career woman who doesn’t understand that she’s going to regret not having kids when she turned 50.”

That’s why we’re so clear that this book isn’t directive. It’s just talking about the stuff that we all talk about.

The way you write about the decision to have children reminds the reader that women have to be aware of our bodies in a way that men don’t.

Let’s say we were going on a trip and we were going to five countries—it’s three different climates. It’s basically like, if you’re a man and you have a tan suit for warm climates and a dark suit for cold climates, you’re good. Just make sure you don’t wear whatever the national color for mourning is.

But for women, it’s different. If you’re going to Africa. If you’re going to have a steak dinner in one of the countries in Africa, you have to make sure that you wear a very colorful dress because that’s how you signify joy and celebration. But then if you’re going to the Middle East, we weren’t supposed to wear green, because green is the color of Hamas. And you are going to Saudi Arabia, even if it’s 150 degrees, still cover up, and don’t let them see you sweat.

And so that’s why in the first book, actually, I included a packing list from my deputy Danielle that she used for all the years that we were together. Because you literally ultimately just needed a checklist so that you didn’t fuck up.

What are things that people ask you, that no one ever asks men?

“How do you deal with your emotions?”

Somebody should ask Trump that.

Because of this lunatic as president, men will get their comeuppance.

But, you can be the most put together woman, and yet, all of us, at some point in our lives, have woken up and been like, “God. Why do I really hate myself today? Why does everything feel like garbage?” Only to then realize that no matter how many years we’ve been having our periods, you’re having some low self-esteem PMS, and what do you do? Because guess what, nothing really fixes that. You’ve just got to take a couple of Motrin and get on with your day.

So, what are the best places to cry in the White House?

I was very lucky. I had an office with a door. But also, up off of the west reception lobby, there was one very pretty private bathroom that was mostly for guests. But you could go in there and close the door and no one else could hear you. And it was a pretty room so you could get yourself back together.

You talk about Slow Burn—the popular podcast that broke down the Watergate Scandal in season one, then the impeachment of Bill Clinton in season two—in your book, which also has had a huge effect on me. I think one of the things it made me think of is about all the bodies of women mangled by the political process. Like, Dr. Christine Blasey Ford.

The day [Brett] Kavanaugh was confirmed I literally had a full meltdown in my doctor’s office… When he got confirmed, it is not to be hyperbolic to say that I was generally destroyed.

I couldn’t believe it because, you know, after listening to the Slow Burn podcast, you’re like, you know what, that’s never gonna fucking happen again. Right? Like, that’s never going to happen again. We believe women.

You can be the most put together woman, and yet, all of us, at some point in our lives, have woken up and been like, “God. Why do I really hate myself today? Why does everything feel like garbage?” Only to then realize that no matter how many years we’ve been having our periods, you’re having some low self-esteem PMS, and what do you do? Because guess what, nothing really fixes that.

But what I love about Slow Burn, and Monica Lewinsky’s story, is that there is redemption.

Well, when you think about it, it took her 20 fucking years. And the truth is, she’s not someone who did anything wrong. So, we talk about, “This is her redemption,” and I think, “What the fuck did she need to be redeemed from?”

And the thing, too, that I really wanted to drive home in the book, is that when Monica Lewinsky had the chance to just save herself, when she had the get out of jail free card, she literally thought about America first. What man would have done that? And so, there she is in her fucking spandex workout outfit at the Pentagon City Mall, which if you have ever been there is a very sad place to get nabbed by the FBI.

Is there any happy place to get nabbed by the FBI?

Well, it was not the Pentagon City Food Court. [But] she did it, and that’s why, to me, she is the smartest, bravest, most empathetic person I probably know.

What do you think it is about Monica’s story that really resonates with so many women in America?

I think that if you’re an older woman who experienced it, you sit there and you’re like, “Fuck, first of all, she was my age; my God, how did I not stand up for her? How did I not take to the streets for her?”

And for younger women, they’re just all like, “You’re fools. What was wrong with you? You’re bad women. What part of the story did you not understand?” There was one victim in that story and it’s her. It’s not him.

In the book, you write about how you worked so hard to not cause an international incident with your toes. [Editor’s note: During a 2009 trip to Saudi Arabia with President Obama, Mastromonaco was informed that, as a woman, she was not allowed to wear open-toed shoes. When they landed, however, she quickly realized she’d packed the wrong pair—and had to try and hide her toes as best she could when she met King Abdullah.] Meanwhile, the people in charge of the White House now don’t seem to have the same standards. Does this make you kind of want to give up?

It genuinely hurts my heart because these are standards that weren’t just set by the Obama administration, they had been set for many, many, many administrations.

When I left the White House, I was ready to go into the sunset and just listen to the Grateful Dead, get a proper job that made me some money, and smoke weed. And now I feel like we all have to be at DEFCON 5 because all of us, even like me, like Nicole Wallace on MSNBC, Dana Perino on Fox News who also worked in the Bush administration, I feel like we all feel like we have to be hyper-vigilant and reminding everyone, every day that this is not how it’s supposed to be. The thing that I don’t know, and I guess we’ll find out, is like, do we all have to go back into the administration in 2021 and make sure that we set everything right?

Why is raw honesty necessary?

Even in the 2020 race, what are people looking for? They’re looking for someone who’s just going to tell them the truth, which is why I think that Bernie [Sanders] still has a relevance. Because I think that he is someone who, agree with him or disagree with him, has largely told his truth for the last 40 years, and people don’t want to see someone who has poll tested what they should say and what they shouldn’t say because guess what? In two years, the poll might change, and then how do you know what they’re going to believe or what they’re going to do? So I guess I want to hold my folks to the same standard that I would want my president or my congresswoman or my senator to hold themselves to. Ask me questions, I’ll give you an answer, which also means sometimes I might say I don’t know the answer. Which is a perfectly fucking fine answer.

This interview has been edited and condensed.

Lyz Lenz’s writing has appeared in the Huffington Post, The Washington Post, The New York Times, Pacific Standard, and others. Her book God Land is out August 1, 2019, through Indiana University Press. She lives in Iowa with her two kids and two cats and is a contributing writer to the Columbia Journalism Review.

Photo: Pete Souza, Public Domain