A BRIEF INTERLUDE ON HOW TO BE RESPONSIBLE WITH MONEY
It’s not very sexy to think about personal finance, which is why so many people have no control over theirs. Unfortunately, it never really gets fun! But there are things you need in your back pocket in order to live life how you want. I didn’t have any of them when I left the job as rubber secretary at Merrill Lynch.
First, your credit score matters, and monitoring it is your job. (Checking your credit score doesn’t lower your score, which is a common misconception I believed for a long time.) I would flag this as a major item for anyone looking to work on a campaign or at a start-up, where things can be a little “loose.”
For example: When I was on the Kerry campaign in 2003, I managed our relationship with our air charter company. A senior person on the campaign told me I would get my own credit card. Awesome, right? No. 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, when I wrecked the Toyota Corolla my pop gave me and was rejected for a $5,000 auto loan when I tried to buy another car; I got to work so early and left so late that a car was a necessity, not a luxury. It had not occurred to me that they were using my social security number to get the card—I should have guarded it with my life.
Second, savings. I’m sure you’ve all read about having a “Fuck You account.” If not: A Fuck You account is the money you keep around in case you need to say “Fuck you!” to someone or something, fast—a boyfriend or girlfriend, a terrible job, a shitty landlord. The more money you have in savings, the more mental space you can give yourself in making decisions, and the more secure you’ll feel. I babysat after work a few nights a week and on Saturdays until my schedule absolutely did not allow it—through my entire time in Boston working for John Kerry and for many of my first years in DC. After the Summer of Unemployment, I vowed to always have money in the bank, no matter what—even though I never had a job that paid well until a few years ago.
I was especially diligent about putting money away on the Kerry campaign after the car debacle. (I used the $1,500 I had in savings to buy a 1988 Saab. This was early 2004.) Working on a campaign is very risky, in terms of job security as well as salary—your employment is guaranteed only as long as your candidate is alive and has a chance at winning. (This is even truer today: With social media and a 24/7 news cycle, it doesn’t take much to start losing.) By the time the campaign ended in defeat, I had about $3,000 in my savings account, which was enough to pay my rent and expenses (on Campbell’s soup, PB&J, and, as a treat, McDonald’s) for about three months. When Tey and I drove out to Anacostia to sign up for unemployment, there was a line in the office just for Kerry campaign people. I didn’t sign up, and I don’t think she did either. We were convinced we would get our shit settled before we ran out of money.
Luckily, we both did—Tey started working for Senator Maria Cantwell, and I started working for Senator Obama a month or so later. But in the meantime, I never bought coffee out, got a manicure, or went to the grocery store without coupons. Like I said, not sexy.
I really liked New York City, even if it is a hard place to truly succeed. I took early Saturday morning walks up to Central Park. We explored weird little bars (only after pregaming with some cheap booze and Crystal Light to ensure we had to purchase only one drink when we were out) and ate gravy fries at Milady’s (sadly, no longer around) when we were feeling fancy or got a paycheck. Otherwise, we would have a lot of turkey sandwiches from M & O Market on Thompson Street, or tuna on Wasa crackers with mustard. My favorite memory is when Cara and I played hooky from work and ate at the Cub Room (also no longer around). We had cocktails during the day, which was very exciting to me at the time. (I feel like day drinking really only came into its own a few years ago.)
The thing is, though: The work scene at SenseNet wasn’t me, and it kind of bummed me out; I was beginning to think nothing was really me. I did what I was supposed to (filing, faxing, answering phones, learning about “the Internet,” making appointments and lunch reservations) with a good attitude, but it was not even remotely stimulating. I left after a few months—a few months after that, SenseNet was bought by another company and everyone got really rich—and got a job at Sotheby’s.
“Wait,” you’re saying again. “What?” Why not! I did client relations in the international realty division. The money was fine, the wardrobe was at least somewhat relaxed, and it took me to a different part of town—the Upper East Side.
By this point, bouncing back and acclimating had become my thing. I made fast friends at Sotheby’s. My boss was Tom; he was really intense and loved his job a lot. I couldn’t understand how anyone could feel so passionately about real estate, but he did, and instead of mocking his love of luxury property, I went with it. I learned a lot about the difference between mansions, estates, cottages, and “important homes.” It’s best to have your home oriented toward the sun (though one must be careful of too much southern exposure). “Historic” is often code for “money pit.” I listened closely as Tom talked his clients through their options. Now, 18 years later, I’ve had the opportunity to impress a lot of doubtful men with weird factoids and assessments.
I was there for a few months, and I got pretty good at real estate. I liked making brochures and talking to clients; I had my favorite properties. It was really pretty fun.
But a few months earlier, I had visited Volpes in Boston, where I saw John Kerry give a speech on TV. What if? There was nothing really remarkable about the speech, but I had not seen a political speech in so long that I had almost forgotten how exciting it was to hear someone talk about possibility and change—to hear something aspirational. I felt like myself for the first time in a long time.
I sent a letter to his intern coordinator in the winter of 2000. I say “letter,” but it was really more of a plea. I said that I knew I was meant to work in government, and that I would do anything to make it happen. I said I was willing to intern even though I’d been out of college for a couple of years, and I wasn’t just bullshitting. My internship for Bernie was more satisfying than most of the jobs I’d had, and I had done it while earning enough for rent and expenses with a smattering of supplemental jobs—I could do that again. I was convinced that if I could just get my foot in the door, I would end up with a job.
About two or three weeks later, I came home from work to a message on our answering machine: Someone at Senator Kerry’s office wanted to discuss my interest in working there. (Note the difference between “interest” and any mention of an actual job.) At long last, after a series of roles that seemingly made no sense and that I took for no good reason, I got the call I had dreamed of. Sort of.
I went up to Boston twice for interviews. The first time was sort of “informational”—but you should treat anything called “informational” as the real deal, because you never know. I wore the brown suit. I brought fresh copies of my résumé on good paper. I read up on everything and anything John Kerry. I even memorized a few quotes that his press secretary, Kyle Sullivan, had given to the Boston Globe. (This was before the real Internet, so I actually had to buy copies of the paper and scan the clips.) These were adults taking time out of their day to meet with me, and I was going to attack the meeting.
A few weeks later, I made a second trip, and I met with the state director, the press secretary, and the scheduler. I dropped all the information I could mostly casually fit into the conversation, but I also conveyed that I would do whatever it took to make the most of the opportunity. I talked about “no job being too small for m
e,” 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. I did end up answering the phones a lot. Before I left that second interview, Senator Kerry walked into the room. He blew past me and into his office, but then I heard him ask who I was. His team told him I was interviewing. He asked for my résumé, and I heard him say, “She worked at Sotheby’s—she must be good.” 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.
I got a call a few days later from Jeff, the state director, and he offered me the position of assistant to the press department and the scheduler. I would take shifts answering the phones and dealing with mail for $20,500 a year. I did not hesitate in thanking them for this blessed opportunity and immediately started thinking about ways I could spice up Top Ramen. I was totally giddy. My last week at Sotheby’s coincided with the series finale of 90210.
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.
In the summer of 2012, the White House was in the middle of a reelection, so I had to coordinate plans related to that on top of my ordinary responsibilities. Here’s a typical day:
650AM: Drive through West Exec gates to ensure my parking spot
655AM: Grab a latte at Navy Mess
700AM: Read national security book or press clips, or watch the news
730AM: Senior advisers meeting in the chief of staff’s office
830AM: Senior staff meeting in the Roosevelt Room
905AM: Ask Clay why my English muffin is cold / Talk to Kathy and Pfeiffer about latest episode of Girls (seriously)
1000AM: Meeting with WH Office of Management and Administration (M+A)
1050AM: Talk to Clay and Pfeiffer about lunch orders and discuss soups of the day
1100AM: POTUS meeting with senior advisers
AM/PM: Weekly planning brainstorming meeting (small)
AM/PM: Weekly planning in the chief of staff’s office
AM/PM: Weekly nominations and confirmations meeting
AM/PM: Weekly Cabinet affairs update meeting
AM/PM: Weekly WHMO update
AM/PM: NSC weekly planning meeting
600PM: Wrap-up in chief of staff’s office (it was anyone’s guess what time this would actually start)
730/800PM: Walk through door / feed cat / uncork wine
In 2012, we traveled so much that, often, many of the weekly meetings would have to be packed into one day, or done from AF1 or by phone in the motorcade. Then you layer in coordinating (lawfully) with the campaign, Obama for America (OFA), so you don’t fuck up their mission (get Obama reelected) and they don’t fuck up yours (keep the government running so that Obama will get reelected so you can keep the government running). I managed the interactions between our Cabinet secretaries and the campaign, making sure that whatever they did—appearing at events for candidates, speaking at state party events, or doing fund-raisers—complied with the laws that cover government officials and political activity. It was not easy. One wrong word, and you could become a headline. I also worked with the Romney campaign to make sure that their most senior staff began getting national security clearances, to have that process under way in the event Romney won.
National security clearances are a funny and worrisome thing. Clearance begins with a form called the SF86, and, notoriously, there’s a section that asks you about drug use.
I smoked a lot of pot growing up, in high school and college and afterward. I hadn’t smoked that much on the campaign in 2008, but even then, I had done it. I didn’t really think about it; obviously, when you’re at the White House, you don’t smoke it, but come on. Most of us on the Obama campaign had worked in the Senate before, so we thought we’d experienced what it’s like to work in the national government, but we’d had no idea. The White House is a totally foreign place.
When I got the SF86, I freaked out. It asks what drugs you’ve done, and there’s a place to write how many times you’d done them. I’m very honest, so next to marijuana, I wrote, “Unknown.”
At times, I was able to pretend like the SF86 wasn’t a big deal, just a normal bit of tedious bureaucracy, but I was terrified. It had never, ever occurred to me that marijuana was something that could keep you from a job. Was I going to have to tell my parents that I couldn’t work in the White House because I’d smoked pot? What lamer and more embarrassing experience could a person have?
Shortly after you fill out the form, an FBI agent interviews you. She brought in my form, and soon—I can’t remember when in the interview; I only remember freaking out about the weed and babbling on about a time I accidentally went to a strip club in Miami with my friend Samantha—she asked how many times I had smoked pot.
I said I didn’t know.
She said, “More than twenty?”
“Yes,” I replied. “More than twenty.”
“More than a hundred?” she asked. I was sweating.
“Yes,” I said, dying. “More than a hundred.”
“More than five hundred?”
“Just write ‘unknown’!”
Do I think pot should be legal? Hell yes I do. Not to validate my use of it, but because I believe that it has health benefits, many more than some other substances that are legal. Was I aware of some of the risks of smoking pot when I did it? Yes. Had I known at age 18 that smoking some pot would be so impactful later in life, would I not have done it? Who knows. FBI agents had to contact all my friends to ask them if I had smoked weed; when I called these friends to prepare them, they were quick to assure me they would say they’d never seen me do it, and I had to tell them, “No! Please tell them that you’ve seen me do it!” (The government needs to see that employees can’t be blackmailed, and that they aren’t truly delinquent, or liars.) For the first year of my time in the White House, I was randomly drug tested almost every month.
Part of my job at the White House was vetting people’s histories—relationships, interactions with foreign nationals, drug use, employment and housing history—to understand their fitness to work for the president. I saw some shit. Tax problems with nannies who applicants declare as employees but then obviously pay under the table. Weird personal web pages about practicing witchcraft. Those were the people who got left behind in the vetting meetings. But almost nothing I saw back then compares to what I see on Twitter or Instagram now. If I had to answer for photos I took in college (I speak mostly about the phase when I was dedicated to looking like Janeane Garofalo in Reality Bites), it honestly wouldn’t be that bad. Things you say on Twitter are probably less shocking now than they were at the beginning of the administration, when social media was new, but if you want to work in public service, you still really have to be careful. You don’t realize when you’re just living your life that it can come back to haunt you. I recently saw a Twitter post from someone I know about doing cocaine in a foreign country. It’s very hard to un-see those things.
The summer of 2012 was one of the most challenging periods of my professional life. While I was coordinating with the campaign and the Romney team, we went on a bus tour through Iowa. This was fun—we ate roasted turkey legs at the State Fair while Axelrod talked to Barbra Streisand on the phone. Then Benghazi happened: Islamic militants attacked the American diplomatic compound in Benghazi, Libya, on September 11, 2012, killing the American ambassador to the country, a foreign service information management officer, and two CIA contractors. From
there, we headed into the three presidential debates, and the first one, in Denver, didn’t go so hot for us. POTUS came back with vigor at the second debate at Hofstra University, but a little more than a week before the election, Hurricane Sandy came barreling up the East Coast.
That close to an election, you have your core team in the White House making sure the government is still functioning as it should, but a lot of people are on the road—traveling with POTUS, doing Get Out the Vote, speaking at events, etc. When we were doing our transition meetings with the Bush administration back in 2009, they told us that Hurricane Katrina happened on a weekend many White House staff members were away; no one was making excuses, but they were paying forward a lesson: Make sure you always have a core decision-making team in the West Wing at all times.
As part of my job as deputy chief, I worked with FEMA, the Department of Homeland Security, and the National Security team on short-term and long-term responses to and recovery from natural disasters and coordinated those efforts across the administration. We also worked with state and local governments, local churches, nonprofits, and utilities companies. With climate change, it wasn’t just Atlantic hurricane season (which runs from June 1 until November 30) that required more vigilance; there were year-round challenges. Droughts. Wildfires. Floods. You name it.
I had experience working on emergency management—I was with Obama when he was a senator during Hurricane Katrina, and I watched how he handled it. He really tried to listen to local citizens and officials to give them what they needed—not just what he thought they needed. When the storm hit, he was in Russia for the Senate Committee on Foreign Relations; he wanted to head straight to New Orleans from there, but we convinced him not to. We decided instead to work with a conservative senator from Mississippi, since most efforts were going to Louisiana and New Orleans specifically. 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.”
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