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

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.

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.

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.

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.

For me, leadership has always been much more about rallying people around a project or cause than about being held up as the Boss.

one of the hallmarks of a great leader is being able to explain your decisions.

A real leader would have delegated and enlisted help, but few 22-year-olds are real leaders.

What you realize is that everyone has her own priorities—her own constituency. Often, being a leader is not about making grand proclamations or telling people what to do; it’s about balancing all these priorities and constituencies.

Women need to know they are right before they stand up. Men are OK objecting if they just think they might be right. I thought, but I didn’t know.

The scene was surreal. Reverend Jesse Jackson was trying to lift Oprah up so she could either see better or get over a fence. Brad Pitt was standing next to us and crying.

He never yelled or demeaned people—even if you let him down, he would move on if you admitted it up front. He assumed we were all adults and learned our own lessons.

Four newly industrialized countries—Brazil, South Africa, India, and China (BASIC)—formed an alliance just before the conference and committed to acting as a bloc in order to protect themselves against what they viewed as limiting measures from developed nations.

Persistence will get you far, and leaders have to champion the push.

Of all the departments, I thought the WHMO would be the toughest nut to crack—it was complex, scary, and procedural, and there was no cheat sheet to understanding it. You met with WHMO in a conference room in a part of the White House that you’re not really supposed to talk about, and I would often be seated with high-ranking military advisers and decorated generals. I was worried I was going to look like a complete amateur when I had my initial briefing with them. It was scheduled for the first week I was deputy chief.

There is no bigger compliment than being intellectually curious about what someone else spends his or her days doing—it turned out that not having the answers did me no harm. The feedback I got was that the WHMO directors all “felt good about my leadership.”

Sometimes you crush the trip, and sometimes the trip crushes you.

When you tell someone, “Here’s the thing: I might have to shit on this helicopter,” and they don’t shun you afterward, you have a friend for life.

Preparation is protection you can create for yourself; for some people, the hard part may be balancing precautions with paranoia, but in my experience, you can never be too prepared.

If I went through life cramming like every day was the SATs, it would be a miserable existence, but being in control and taking a beat to think about the next five steps—about what comes next—is critical. You would be surprised what five minutes here, 15 minutes there, can do to make you feel confident and ready.

Executing a foreign trip as a presidential candidate means you’re not entitled to support from the US embassies in each country.

Here’s the thing about being a decent businessperson: When you are reasonable, savvy, and polite, you get far.

I know I am rarely, if ever, the smartest person in the room. And that’s totally OK. What’s not OK is (1) not recognizing that and (2) not coming ready to participate in a meaningful way.

all in all, it was a pretty low-stakes protest—but maybe that was a blessing. It made it feel easy—and fun—to get involved in politics, and I couldn’t wait to do something like that again.

if a $1 jelly donut makes you really, really happy, you can get through a lot with a little.

Jobs like this—the kind of job of which there are many, the kind that are definitely good but that no one teaches you to want—are found only with an open mind and a willingness to do your own thing.

If you do it responsibly, quitting something that isn’t benefiting you—whether it’s dance classes that “everyone is taking” or a soul-sucking job that has nothing to do with anything you’re interested in—can change your life.

Our store was one of only a few that accepted food stamps in the area, which gave me more perspective than almost anything else I experienced growing up. It’s a moment when you see a woman with a kid, or an older person, trying to figure out what the food stamps cover. The humiliation they can endure while holding up the line, or having to put things back. It forever formed my opinion on how we should help those in need: humanely and respectfully.

My job was never policy focused; I scheduled and coordinated and planned, dealing with times and dates as well as with personalities. But I often sat in on policy meetings so that I could understand our priorities and be able to use my judgment as my team decided, out of a hundred different choices per day, how best to use POTUS’s time.

if you’re just dealing with things as they’re happening, you aren’t prepared for something to come out of the blue.

From the beginning of my career in politics, I had a personally imposed policy about swimming in my lane and not overcommenting on things I wasn’t an expert on. But in this case, I could not take the pontifications of this Ivy-educated gang; they were talking about the limits on what food stamps cover and don’t, and I could just tell none of them knew one person who had ever needed food stamps. I raised my hand (something I think only I did when I wanted to talk) and told them what it was like to see people humiliated in line trying to buy generic cereal, canned soup, milk. To watch them realize what they couldn’t get. To watch them realize how ridiculous it was that sports drinks were covered but something like Sunny Delight—which is actually much cheaper than orange juice but still has a decent amount of vitamins—was not, but that there was nothing they could do. I could feel my face get red and hot. I usually think you start losing your argument when you physically reveal how worked up you are, especially in a place like the White House, where, theoretically, what you say should be based on facts and figures and evidence; if your face is red, aren’t you showing too much emotion? I don’t know, but I got my point across. It wasn’t a conversation intended to resolve or change anything at that moment, but POTUS made it clear he was on my side.

a lot of times ambition in Washington is just about being powerful, and you can be powerful without a seat in Congress.)

I was busy every day walking briskly and professionally over the halls of Congress.

Never brag about your ability to type. It will never get you anywhere you really want to be.

Always ask to see where you’ll be sitting.

Forward motion is always better than no motion—even if you don’t think it’s taking you in the direction you wanted to go.

Being self-aware means knowing when you’re about to act bad—and then not acting bad.

Make sure you always have a core decision-making team in the West Wing at all times.

I vividly remember being on a conference call and, in the middle of a discussion about how to send supplies to the area through the Mississippi senator’s church in Pascagoula, hearing Obama say, “I want to make sure we’re sending enough feminine products to the Gulf Coast. I’ve heard they really need that. Diapers and feminine products—that’s what people need.”

For some people (like me), gathering the courage to speak up in meetings is a skill that requires practice. There are always the normal fears—that you’ll sound stupid, that everyone else has already thought of what you’re about to say and has moved on, that what you thought was a foolproof plan will have an obvious hole in it.

On our way back to DC, I asked Fugate why no one seemed to be taking from the pile of clothing donations I had seen at a Red Cross location. He explained to me the survivor-versus-victim mentality: If you had lost everything and were told you could dress yourself in hand-me-down jeans and shirts that didn’t fit, would that make you feel empowered, more in control? No. A $75 gift card can be much more helpful in propelling someone forward. So when corporations asked what they could donate, he was not shy about asking for gift cards.

I wear every thought on my face; POTUS knew immediately that I was mentally rating each person on my team on a scale from innocent to “deserves another irrational email.”

Developing self-awareness is a lifelong process; you don’t just wake up one day and have all you need. So even though I’d spent the last few months demonstrating that I was capable and knew what I was doing, this was something of a revelation.

generally as it relates to any kind of replying-all in life: Think about how what you say could affect people, from the top down.

America is a nation of people who work a lot and of people who strive to work a lot.

Every time you change jobs, even if you’re coming in as the editor in chief or senior marketing manager or whatever, you will have first-day jitters. You will still spend an hour (or two) thinking about what you should wear. Those jitters don’t mean you’re about to fail; they’re what get you ready to dive into something headfirst.

Every decision we made had to stand up to the workhorse vs. show horse test.

One of my main goals in writing this book is to give you the permission to admit to feeling or doing things that are silly; once you do, you can get on with your life.

Often, when you’re dreading something, it can feel as if there is just no possible way that whatever you’re dreading will actually happen—as if some goddess of serendipity will surely swoop in and stop it in the nick of time. The test you haven’t studied for will be rescheduled for next week; the guy you’ve really been meaning to break up with will tell you he’s decided to move to India to embark upon a life of meditation but will always love you and remember the times you shared; the cockroaches in your apartment will be revealed to have been a very involved art project your roommate was working on, so you won’t have to argue with the landlord and call the exterminator nine times and be afraid of going to the bathroom in the middle of the night for several weeks.

I also needed a staff; where I would find one was less obvious. The scheduling and advance world was made up almost entirely of people who had cut their teeth with the Clintons in the ’90s. The Hillary team had already started recruiting, and the message was clear: Do anything for Obama, and you are dead to us. I was screwed. My message was, “Dear God, please help me. I trust you enough to do Clinton events, too, please just help me, please, please, please.”

Each night after that, she and I took the pitchers and forks home to wash because the only sinks we had were in the bathroom, and they were too shallow and didn’t have hot water.