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

Information was the tool I needed to do my job, and I couldn’t figure out where it was or how to get it.

There are moments when you catch yourself wondering how you look walking off Marine One—wind blowing in your hair, serious leather bag at your side, adjacent to the man who runs the country. There are also times when you actually walk off Marine One with the president on a Friday afternoon in rural Virginia, climb into your armored Suburban, and are told by a member of the medical team that you have split your skirt clear up to the zipper. Those are the moments you should remember: when your coworkers are rallying around you to keep you from showing the president your really old Hanes Her Way underwear. When they pin you together and you have to lie sort of sideways in a mermaid position so you don’t bust the pins.

In DC, you can get some level of power from the person you work for, but the minute you forget power comes and goes with elections, that’s it. You may think you are hot shit for working at the White House, but there is always hotter shit around the corner. You are staff, a helpfully lowly term.

When it became obvious that planning even the most basic wedding would be too much, someone told me that Elena Kagan and Sonia Sotomayor loved officiating at the Supreme Court. This seemed great. I bought a short Stella McCartney dress from Farfetch (blue with wide sleeves), and we scheduled a Friday afternoon with Justice Kagan, who was glad to have us.

There’s not a real resolution here, except the lesson that you should be able to accept the fact that sometimes you’ll fuck up, have to sincerely apologize, and try to move on.

I had a list of questions for the mayor; the most important was “How would you set me up for success?” Generally, if you’re coming in to take over a department, you want to know that your boss will demonstrate to everyone else that you have his or her support. You also want to know whether you get to hire people or make staffing or structural changes.

When you go from checking your BlackBerry 500 times a day, needing to be available and responsive 24/7, to being able to sleep until 8:00 AM, wake up, have a leisurely breakfast, and do whatever you want—it sounds awesome, but you also wonder why no one is calling you. Weren’t you invaluable? Irreplaceable? We are all replaceable. Life goes on, but that doesn’t mean it feels good.

if anyone asks you to tell them what you want, you should respond as follows: “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.”

One of the good things about being resilient is that, when you’re forced to veer off course, you pick up skills you didn’t realize you needed.

Being resilient means being honest: You have to admit when you’re struggling. Usually, someone will help you.

There are certain lessons you pick up gradually as you go, letting them accumulate after a series of similar mistakes or experiences until you finally realize you’ve been a fool all along. And then there are the lessons that are so massive they smack you in the face—you don’t reflect on a period of your life and realize, “Oh, I learned something then”; you know it’s happening when it’s happening. The importance of kindness—which extends far beyond “please,” “thank you,” and “your hair doesn’t look bad today”—is a combination of both:

Over and over in my life, I’ve been bowled over by how kind people can be, and how that kindness can change your outlook. Politics is often associated with secret dealings, competition, and corruption—and those associations aren’t necessarily wrong—but, fundamentally, it’s also about people and personalities. Working at the White House is obviously heady, but it’s also humbling—you’re around the most brilliant, decorated brains in the country. They don’t have to do anything for you, but they often do. If you approach it with grace—and a willingness to accept that many people know much more than you—you can walk away a much better person than you were when you came in.

Kindness often exists on a smaller scale than the grand gestures popular on social media would have you believe. Though anonymously paying off someone’s student loans or giving a waitress a $5,000 tip are amazing acts of goodwill, things like being willing to cut someone some slack, or making a thoughtful phone call, can help another person so much.

was so worried: that I would never see my friends again, that I would never be successful on my own, that I had given up the one thing that made me who I was. But as I adjusted, sometimes painfully, to my new life, I realized both that I could live without it and that it would never really go away—not least because politics affects most, if not all, aspects of our lives.

Politics will always be a twinkle in my eye—the thing that makes me say “What if?”