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

Barack Obama was on TV being smacked in the face by sleet. So much worse than snow. Basically worst-case scenario. We watched (in horror) as the event drew to a close, and Obama reached his hand to Reggie. As we were turning off the TV, my phone rang. “Alyssa, it’s Obama.” “Hi!” I said, with my head down on the desk, girding myself for the inevitable and deserved. “The event looked AWESOME! You heard John McCain canceled all of his events, right? He looked like a total old man!” “Alyssa, where are you right now?” I was not sure where he was going with this, but I knew it was somewhere bad. “My desk,” I replied cautiously. “Must be nice.” Click.

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.

The next year, Damon Winter, a photographer from the New York Times, received a Pulitzer Prize for his coverage of the campaign, and the winning work included a photo he took of the event.

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I made it my mission to get a tampon dispenser in the West Wing women’s bathroom. If we were truly serious about running a diverse operation and bringing more women into politics, 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. There was no objection to my proposal; it just seemed like no one had thought of it before. I went to the head of the office of management and administration, Katy Kale, and said, “Hey, we should put a tampon dispenser in the women’s bathroom,” and she said OK.

I announced the West Wing would be installing a tampon dispenser in the women’s restroom that day. No one said a word, but it felt really good. I realize I promised you that I didn’t want to focus on “my legacy” in this book, but since they didn’t engrave the tampon dispenser with “Made possible by Alyssa Mastromonaco,” I wanted to leave a record of it somewhere.

I wanted our senior band trip to be to New Orleans. My platform was solid; all the members of the band agreed that we should go to the competition in NOLA. But we ended up in Philadelphia. Maybe sometimes rallying support for your ideas isn’t enough; maybe taking 40 teenagers to Bourbon Street will always be a hard sell to the principal.

They asked where I wanted to start. I opened up my crazy-looking Post-it commercial of a binder and began with the first question, which was about the helicopter replacement program. After they gave me answers, I had more questions. I think the meeting lasted two hours. But about 30 minutes in, I got into the groove. The questions kept coming, and so did the answers. Before I knew it, I was understanding it all. 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.”

I was pretty young when I read Are You There God? It’s Me, Margaret—the edition from the early ’70s, where they still explained that maxi pads had belts. Maxi pads used to be held in place with a weird string-and-loop system, and that is what I learned about. By the time I actually got my period, I was very confused. Where were the belts?

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.

From what I can re-create of the disaster, my social security number was used to get the card. This card had a balance of roughly $150,000 in charter fees at any time. At the end of 2003, we wanted to show a lot of cash on hand in our campaign bank accounts—a sign of viability when the numbers are publicly released at the end of each quarter—so we did not pay the air charter bill for about two months. This meant that for more than 60 days, I had an outstanding balance of about $500,000. It completely destroyed my personal credit, and I only found out months later,

The Kerry 2004 campaign used co-signed employee SSNs to obtain huge amounts of credit and then stuck them with the dings.

I talked about “no job being too small for me,” and I remember saying to them, “If I can’t answer the phones right or get the clips done on time, why would you give me anything else to do?” Self-awareness—it always impresses people.

A voice said, “Alyssa?” OH MY GOD. I knew the voice. He didn’t immediately say, “It’s Bruce Springsteen,” but he sounds just like his music—it was like a saxophone could come in at any minute. He thanked me for my work on Hurricane Sandy on behalf of the people of New Jersey. Because I am a real tool, I was so shocked and flustered that I told him he probably had better things to be doing on Air Force One than talking to me. I said I appreciated his call, and then we hung up.