As a family, we picked a few schools to visit—Georgetown, Berkeley, Stanford, UC Santa Cruz. I didn’t end up applying to all of them, but the places I did apply to—University of Vermont, University of Wisconsin, Cornell, Brown, Georgetown, SUNY Albany, and Fairfield—I did myself. I wrote the essays, which no one proofread, and studied for the SATs and did pretty well. (Especially in verbal.) My mom did help me fill out the checks for the application fees—and disclaimer: They were my mom’s checks.
If you haven’t seen St. Elmo’s Fire, you won’t really be able to fully understand my mind-set at the time, but I really wanted to go to Georgetown. The movie takes place in the year after a group of friends graduates from there and tries to find their way in the world. For some reason, even though I hadn’t really thought much about getting into politics at the time, I wanted to be Alec; he was a very self-important 22-year-old working on a congressional campaign and cheating on his live-in girlfriend, Ally Sheedy, who was too good for him. The characters were very weird role models: They drank a lot, a couple of them did a lot of coke, and they spent too much money. But they were attractive and funny and ultimately made it out alive. I credited all this to the fact that they had gone to Georgetown. I thought that if I got in I would be able to access some of that Brat Pack energy.
I was top 10 in my class (and by top 10, I mean number 11 of 76) and not short on confidence. Who wouldn’t want me?
I got all my rejections on the same day in April. After returning from our second pilgrimage to Georgetown, where I had bought a car sticker because I was so convinced I was going to get in, we got home to realize the cashier had forgotten to put the sticker in our bag. Later, when my dad got the mail and I opened my very thin letter from Georgetown—and all the others—we realized it was a sign. (Signs like this work only in retrospect.)
I ended up choosing between the University of Vermont and the University of Wisconsin–Madison. Coming from such a small town, I was worried I would be too fish-out-of-water-y in Madison, so I happily and proudly signed up to be a Catamount in the freshman class of 1994. When I sent in the forms to register for housing, a meal plan, all that stuff that makes you feel like your new life is about to start, I had never set foot on campus.
Sometimes I do leap and then look, for better or for worse. Sometimes it works out great. Other times… maybe things could have gone a little better.
If I had a sense of myself in high school, I lost it in college. This was the first time I realized that money mattered and how you spent it mattered more, and since my family put value on getting the most out of your car—I thought Ford Taurus station wagons were aces because they lasted forever—I had no idea who I was. I grew up in a town where you didn’t know who had money and who didn’t. The wealthiest families were probably the equine veterinarians, and they drove beat-up Suburbans and Wagoneers. I don’t really remember anyone wearing makeup, save a little cover-up for sweet teen acne. I wore clothes from the Gap or Marshalls, and my hairstyle rode the wave from Magic Mushroom bowl cut to Eddie Vedder shag. (Think about it: When his hair was shorter, the layers were very similar to the Rachel.)
It wasn’t all bad. I was good friends with my roommate, Amy, and our floor had a lot of Joni Mitchell and Indigo Girls listening sessions, and a lot of talks about “what bugged you out.” The mid-’90s “bug out” could describe any number of situations: when you encountered someone weird, when you smoked bad pot, when you experienced your first bout of insomnia because the guy in Intro Psych didn’t sit next to you and you just couldn’t figure out why. In retrospect, this was very fun.
My classes helped me branch out, too. I majored in French and also became very good at Japanese, which I signed up for on a whim. One semester I took a course in rural sociology, which focused on poverty in the Northeast Kingdom of Vermont, and I later used what I’d learned to make small talk with Oprah while we waited for an Obama event in Iowa to start.
Still, around the beginning of sophomore year, I began to realize my French major was maybe not taking me in the direction I wanted to go. Vermont is very political—people say what they think. They disagree without being disagreeable and have discussions without fighting. State and local officials were always on campus; Governor Howard Dean came to register us to vote; I got to jump on a reviled Republican’s car. I found myself gravitating toward the political stuff, whether it was on or off campus. That winter, I decided to apply for a summer internship with Bernie Sanders.
When spring break rolled around, I found out that the budget for the French department was being cut and it might not be offered as a major any longer. I thought this was a sign, so I reapplied to the University of Wisconsin–Madison to transfer in my junior year, and I was accepted. A few weeks later, I also got the Bernie Sanders internship, working from May through August in his Burlington congressional office.
The internship didn’t pay, but I was able to stay with a couple of friends in Burlington, in an apartment on South Street behind a liquor store. I slept on a futon and more than once woke up to see a spider I had crushed in my sleep.
But it didn’t matter: Nothing had ever been more exciting. It was an election year, so Bernie was in the office a lot, and he met with constituents more than any politician I’ve known since. I was kept very busy, which I loved. I answered phones and took down notes from voters. I faxed press clips. I filed. At night, I would call people in all parts of Vermont, trying to raise money. I wasn’t super successful, but I did a great job at reminding people to register to vote and telling them about events Bernie would be doing around the state.
From time to time, I also got to drive Bernie around. He looked the same way he looks now—super disheveled, his tie a little loose, always brusque but fair. He would usually read the newspaper, even though we always had the windows down—never air-conditioning. Sometimes he asked about my family, and where I was from, and explained to me what was going on in the world. I once tried to impress him by telling him about the time my friends and I had climbed on Newt Gingrich’s car. Bernie was unmoved; his attitude was basically, “Well, what else would you have been doing?”
Before I met Bernie, I had always thought politics was about theater and showmanship and that nothing really happened or got fixed. But instead of focusing on the large-scale changes many people expect from politicians, he showed me how to see the people whose problems he could immediately impact and solve. The people who worked for him also seemed genuinely dedicated to helping his constituents, which is not necessarily true of other senators; many politicians have staffs made up of climbers, who move from one senator to another to get up the ladder, with the ultimate goal of becoming a legislative director or chief of staff. (Of course, some politicians’ staff members want to go on and run for office themselves, but a lot of times ambition in Washington is just about being powerful, and you can be powerful without a seat in Congress.) Bernie was so committed to his issues, and to Vermont, that politics didn’t feel gross. Before I left for Madison, I changed my major to political science.
One day at the end of my internship, two important things happened. The first was that I saw a call come in for Bernie from a 608 area code, which was Madison. Bernie was running late, so I told the man on the line, Ed Garvey, that he might have to wait a few minutes.
In the meantime, I asked questions. I always tried to learn about the people coming into the office, especially people meeting with or talking to Bernie; I wanted to know what made them important enough to warrant his time and attention. I researched everything I could.
So when I got Ed on the phone and he had to wait, I saw my chance. I knew that Ed was a very important labor attorney; he had unionized the NFL Players Association and was a progressive leader in Madison. I told him that I was going to be transferring to Madison in a month. He replied that I should come see him when I arrived on campus. I worked for him for the two years I lived there.
The other important thing that happened that day was that Bernie’s
team invited me to be an intern in their DC office the following summer. I don’t know if anyone in that office will ever understand what that meant to me. I felt like Wonder Woman. I was ready to strike out. I packed up and went back to Rhinebeck for a week or two, and then we drove out to Madison.
I saved all my money that year—from working for Ed Garvey, from babysitting for a family outside of Madison a couple of times a week, and all of what I got for my 21st birthday—for my summer in DC. I lived in Tenleytown with a friend from Rhinebeck, Shannon, who was going to law school at American. I drove to the metro, parked, and took the train to Capitol South. I had exactly five outfits to rotate each week. I made tomato and mayonnaise sandwiches and packed some pretzels for snacks.
I walked into Bernie’s office feeling ready to jam, but this was a way different vibe. These interns were kind of competitive, and I’d rather bang in a drum circle all day than ever have to compete. I had a minor crisis of confidence. Then I remembered that I knew a hundred times more about Vermont than these guys.
I was busy every day walking briskly and professionally over the halls of Congress. Getting signatures on bills or amendments. Running anything and everything to other offices and helping to draft letters to constituents. If Legally Blonde had come out by then, I would have fancied myself a version of Elle Woods meets Norma Rae, the union organizer. When my internship ended—and I was basically out of money—I was convinced I would be back the following summer after graduation to start my career as a humble and committed government employee. I didn’t get to interact with Bernie that much, but it didn’t really matter: Working for him had given me back a clear picture of who I was and what I wanted to do.
CHAPTER 4
Self-awareness, or Are You There, FEMA? It’s Me, Alyssa
By the end of my senior year at Madison, I knew I needed to start planning for graduation and the new life I had fully envisioned for myself in DC, so I went to the career office to figure out how to apply for jobs. I wrote cover letters and attached my 22-year-old’s résumé, which still included hostessing, babysitting, and being a checker at Kilmer’s. I was confident; I had worked hard, I was proud of what I’d done for Bernie, and I was certain I wanted to be in government. I applied to be the person who answered the phones for every member of Congress from New York State, Wisconsin, and Vermont. I applied to work for the Democratic National Committee and Democratic Senatorial Campaign Committee. I had no delusions of grandeur. I would have just been happy to be there.
No one called me. No one wrote me back. I called my friends in Bernie’s office, and they broke the news that they weren’t filling any junior positions.
The lease in Madison was up in mid-August. What the hell was I going to do?
Young people are not known for their acute sense of self-awareness, and I was no exception. Unfortunately, that’s by design; you haven’t had a lot of time to get to know yourself yet. The only way to get through periods of confusion like the one I’m about to describe is to ask yourself a bunch of questions and slowly find the answers to them. Who am I? What do I want in life? What am I good at? What am I bad at? Does my hair actually look good with so many layers? Do I care?
To encourage me, in a backhanded kind of way, my pop told me this story about when he graduated from NYU. He had offers for jobs in Hartford, but he really wanted a full-time job at IBM. He was waiting to hear from IBM, but he knew he might have to go to Hartford.
Capitol Hill was my IBM. I thought, Is Pop telling me to go to Hartford?
He was. (Though he himself did not end up having to go to Hartford.)
Before my lease was up, I flew from Madison to Rhinebeck and took the train down to Manhattan to see some headhunters.
Headhunters are rough. It’s their job to get you to take a job, so telling you how amazing you are isn’t on the top of their list; they want you to feel grateful for whatever they land you. And in my case, it was my job as a paralegal at Thacher Proffitt & Wood. My salary was $26,000 and I was eligible for overtime. I had no idea what that meant.
I went back to Madison and accepted that I wasn’t going to work in Congress—maybe ever—but I was going to be an awesome paralegal. Even though I had no idea what that meant, either. My mom took me shopping, and I got a brown suede suit from Banana Republic that I wore on my first day, even though it was about 85 degrees outside.
I did my training with Volpes and Kara O’Leary (Kolea), who was also very cool. A woman named Emma taught us all about Redwelds (accordion folders with ties on them), why you always wanted to have enough lobster traps (metal accordion folders that hold closing documents and keep them orderly), and how to do a Uniform Commercial Code (UCC) filing. The UCC governs commercial transactions in the United States; in 1998, UCCs still had to be done on the typewriter for carbon copies (like physical carbon copies) for Arizona, New Jersey, and Massachusetts, and I did a lot of them. This advice was more relevant a few years ago, but still: Never brag about your ability to type. It will never get you anywhere you really want to be.
I was not rushing back and forth through the halls of Congress, but I was in the World Trade Center, helping lawyers close deals for millions of dollars. That was something, right?
After about a year, paralegals cycle out. Volpes got into law school. Kolea was moving to Buffalo (“the Buff”) to live with her boyfriend (now husband). Because I had spent a lot of time at bars in the Financial District surrounded by finance people, I decided to leave for a job at Merrill Lynch.
“Wait,” you say. “What?” No fucking idea. My friends were leaving, and I had to go, too. Months earlier, I had gone through an arduous interview process to become an assistant in International Paper Trading at Lehman Brothers, only to make it to the bitter end and decide that I absolutely did not want to do that. But working in finance seemed like something a “successful” person would do, and everyone in my crew was doing something new, so I gave it another shot. (In case you were curious, Investopedia defines “paper trading” as the practice of “using simulated trading to practice buying and selling securities without using any actual money.” It lets investors practice trading, basically. I know more about paper trading from looking it up to try to explain it here than I did when I was interviewing for the job.)
The headhunter got me an interview at Merrill Lynch, which was in the World Financial Center, right across from the World Trade Center. I don’t remember much about the process, except that I was offered $35,000 to be an assistant to the managing director in rubber, which I think means that his group analyzed rubber sales and the cost of buying rubber globally. I was really wowed by the salary, which is insane, since I made a base of $26,000 at TPW and got overtime, which meant I grossed about $42,000 in 12 months. Why the hell did I care about $35,000? I got to $42K working crazy hours; this job was not eligible for overtime, which meant that no matter how many hours I worked, I would only get $35K.
In the interview, I did not ask questions. They kept talking about me being “support,” and at one point they asked me how many words I could type per minute, but I didn’t think about it. I was determined to work in finance, and I would do whatever that meant when the time came.
On my first day, a woman from Human Resources took me to my desk, and I saw that it was a desk among many desks that sat outside offices, like in Mad Men. You never want to be able to compare your work environment to Mad Men. As in Mad Men, all the desks were occupied by women. Some very simple but useful advice: Always ask to see where you’ll be sitting.
My heart started to race. I had taken the job thinking I would be the most junior person on the rubber team. What I had not realized, but what my security badge made crystal clear, was that I had taken a job as the rubber team’s secretary.
I told myself I had made my bed and now it was time to lie in it. I sat down. I programmed my voice mail. I got the password to my computer. I tried to care about what people were saying to me. But I didn’t.
I knew I would regret it i
f I stayed, but I also had about $65 in my checking account and no savings to speak of. I don’t know why, honestly. My friends and I didn’t go out to eat much or buy fancy things; taking a taxi to the Upper East Side was seen as a luxury and treated that way. But in New York there is like a $10 toll just for stepping out of your apartment. (Today it’s more like $25.)
I called my mom and dad to tell them I had been duped—well, it was probably my fault, but that isn’t what I told them—and had to quit. I said I might need some money, and they said to ask if I did, but I didn’t want to have to.
I quit by leaving a voice mail on my boss’s office line at the end of my first week (don’t do this) and never went back there again.
It was the infernal New York summer, and our apartment didn’t have air-conditioning. Because I was sitting around in it all day, I quickly broke down and used $30 of the $65 in my checking account to buy an oscillating fan. I had the fan less than 24 hours before my roommate decided to do some cooking in our 75-square-foot living room/kitchen and moved it onto the hot stove. It melted and became a crooked fan that couldn’t oscillate.
Every morning, I would go out to get a paper or magazine—Village Voice, Daily News, Post, New York Times—to check for job listings, which I would go through at the coffee place Cara and I called Suspect Coffee—an equivalent nickname today might be Sketch Coffee. It was kind of vicious of us, since Adam, the guy who worked there, gave me the day-old corn muffins for free after he noticed that I was coming in at around 9:30 instead of my usual 7:00 and I told him it was because I was now unemployed.
I took the free corn muffins and interviewed at loads of places. Tokyo Mitsubishi Bank (I ended up doing a Japanese minor). Some French mineral company. Another place that had something to do with rubber. I ended up as the assistant to the CEO at an Internet start-up called SenseNet on Hudson Street. I had no interest in the Internet, or venture capital, or really anything I was doing, but the people were nice and I could wear whatever I wanted to work and it was within walking distance of our apartment. Sometimes, for a little while, that’s enough. Though I didn’t make much money, I was diligent about putting $10 or $20 aside whenever I could. I never wanted my corn muffins to be in jeopardy again.
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