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

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.

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.

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.

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.”

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.

I don’t want to be too nostalgic, especially because the present day has a lot of benefits—women’s rights, Google Maps—but I think the idea that times were simpler “back in the day” is true in a lot of ways.

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.

Some very simple but useful advice: Always ask to see where you’ll be sitting.

But in New York there is like a $10 toll just for stepping out of your apartment. (Today it’s more like $25.)

I have learned a lot about myself over the years, mostly because I was open to hearing feedback. I wear my emotions on my sleeve. I usually dislike someone before I like them. I’m sensitive—especially when I’m tired or feel I’m being misunderstood. This may sound like the “About Me” section on a bad online dating profile, but knowing this stuff has allowed me to keep my contacts, my reputation, and my sanity throughout a long and often stressful career. Being self-aware means knowing when you’re about to act bad—and then not acting bad.

(when people know they’re getting regular updates, they don’t send you random questions constantly, and you can actually focus on what needs to get done in the interim)

I wish that our culture didn’t demand women have an opinion on this. You don’t have to have an opinion on it. I always respond to the questions with something very diplomatic: I am not a victim, I say. Having kids is one way of being happy, but I too am very happy, and well adjusted; I like my house and my husband and my cats and my job. I have time to mentor young women and to see my parents. Many of my friends around my age also don’t have children, and none of them are super bummed about it. I’m a godmother. And I do really love my cats. This is sometimes seen as sad, or cat-lady-ish, but I think that is sexist. (Let’s remember Hemingway—dude had a lot of cats.)

But when I opened that email—and you’re always sort of nervous to get emails from people you want to get emails from, even in normal situations when you’re not about to head into a disaster area—I moved back from the computer.

Maybe it’s that I lived by Mo Mannino’s favorite saying in the Rhinebeck High School yearbook: “Everyone has an angle.” And he didn’t mean it in the America’s Next Top Model kind of way—he meant it like “Trust no one.” Once you internalize that, it’s hard not to be skeptical of random men when they come within 10 feet.

“I’m sure there’s a salary band for the position, and my hope would be to come in at the high end of that.”

I think a “serious” woman can also be a crazy cat lady, and I will be rescuing cats until someone has to rescue me.