Off the Sidelines

by Kirsten Gillibrand

  I didn’t know any of this when I was at Davis Polk. I was too young and too inexperienced. And I missed a few opportunities because of it.

  Which is not to say that I didn’t work hard. Boy, did I work hard. I didn’t care how many hours I put in or how many weekend or vacation plans I canceled. (I even canceled my first chance to meet my future husband. A friend invited me to join a group of ten planning to attend a black-tie gala together, but I had to work all weekend and couldn’t even break away on Saturday night.) I was single, with few responsibilities. Working until 9:00 P.M. or midnight just meant that I’d miss meeting friends or I’d go to bed later.

  My focus was on the office, where I was deliberate about how I carried myself, how I did my job, and what I said. I wanted to be seen as an excellent lawyer, not an excellent woman lawyer. I wore flats or two-inch heels. My business suits were all black, gray, navy, and brown. (Adventurous for me was a red Talbots jacket, which I wore with a white shirt, navy skirt, and pumps. I had one hot-pink Talbots suit, with faux-pearl buttons, which was mostly for weddings.) From watching the older women at my firm, I gleaned that high heels or body-hugging dresses were not rewarded. One lawyer a few years ahead of me ventured beyond the corporate uniform, and she never made partner or got the respect she deserved. Admittedly, an equally smart, if not smarter, female colleague who dressed head to toe in Brooks Brothers didn’t make partner, either. Regardless, I played it safe.

  My plan seemed to work, at first. The partners liked me because I was capable, dedicated, and eager. They also knew I’d played tennis at Dartmouth, so they often asked me to replace a missing fourth in a doubles match. I filled in for two different games: one foursome at the River Club, the other at Grand Central Terminal. The matches were aggressive. One of the litigators, Jimmy Benkard, started each game by whispering, “Take no prisoners!” (When he sent a donation for my first campaign, he wrote that one sentence on the card he enclosed. I hung it on my bulletin board and didn’t take it down until we won.)

  I loved the matches. I played often and grew to know those partners well, but I also felt a little uncomfortable. I worried about coming across as fun-loving and sporty at the expense of serious and smart. Was this a legitimate concern? I had no idea, and at the time I didn’t have anyone to ask. I had a few women mentors at the firm, but their advice remained in the realm of office politics and the importance of accepting the tough assignments.

  After about a year and a half of playing tennis with the partners, I decided the games could hurt me in the long run, so I informed them that I was focusing on squash and stopped joining their games. I now think that was a mistake. Those matches were a great opportunity to let my bosses know that I was tenacious and fearless, qualities that would serve the firm well. Maybe if those partners saw those traits, one would have sponsored me and taken me under his wing, but, like many twenty-five-year-olds, I didn’t place enough importance on personal relationships. I believed my capabilities would just shine through and I’d be successful on my merits alone. It’s always more complex than that.

  One of the most lasting pieces of advice I got during my Davis Polk years came during a sabbatical I took to work as a law clerk for Judge Roger Miner, on the Second Circuit Court of Appeals. His chambers were in Albany, and my co-clerks and I all had quirky little jobs. In addition to our more serious duties, one of us was the driving clerk, another the library clerk, and I was the soup clerk, which meant I ran the errand of buying the judge his lunch—a cup of soup. I loved delivering it to him in his chambers and having a few minutes to chat about an opinion I was drafting. He took time to help improve my legal writing, but in some ways the most important thing the judge did for me was call me Kirsten. I know that doesn’t sound like much, but up until that point in my life—ever since I was a baby and my big brother, Doug, couldn’t pronounce my name—everybody called me Tina. Judge Miner would have none of that. Kirsten was my formal name, and he was a formal man, so Kirsten it was.

  I assumed I’d go right back to being Tina when I returned to Davis Polk. But shortly after I moved back to New York City, I had dinner at an Italian restaurant with my sister, my father, his girlfriend, and their friend Barbara Jones, who was a judge, too. My parents had separated when I was in college, which came as a surprise to me. Growing up, I always saw them as a perfect couple. They shared a law practice as well as half a dozen hobbies, everything from hunting to golf to gardening. At the time they split I’d had exactly one boyfriend, and the disintegration of their marriage left me so sad, disappointed, and disoriented that for many years my thinking about my parents’ relationship was black and white: mom good, dad bad. I didn’t know anything yet about marriage and how challenging it can be.

  That night at the restaurant, I told Judge Jones about Judge Miner and that I wasn’t sure how I’d like to be addressed now.

  Judge Jones was very definite, saying, “You know, you really should use Kirsten.”

  I was surprised she cared.

  “Yes,” she said firmly. “Tina is too diminutive. You’re a big New York City lawyer. You can’t possibly go by Tina. Your real name has more gravitas. It’s a better name.”

  Kirsten? It still hardly sounded like myself. But I took her advice. I was already a diligent student of how women are perceived, and I realized that, for better or for worse, something as simple as whether you went by a nickname could impact how seriously you were taken. So from then on I introduced myself as Kirsten. Still, to this day I adore hearing someone shout “Tina!” from across a crowded room. It’s a sure sign of family or a very old friend.

  Life at Davis Polk was a grind. For nearly five years I traveled what felt like almost every week, spent ten to fifteen hours a day reviewing documents in windowless conference rooms, and drank way too much Diet Pepsi. To alleviate the tedium and stress, my friend Kathy Baird and I ran almost every day we could. (I finished the New York City marathon twice.) For a few years I also lived with Erin, my sister. She was a perfect counterpoint for me, especially at that stage of life. She was a renegade struggling artist, and I was a straight-and-narrow fancy-pants lawyer. She worked as an actress off-off-Broadway and did commercial work whenever she could. I covered the rent, bought groceries, and paid for our weekly sushi dinner dates. On weekends, I sponsored a student in a program dedicated to taking C and D students out of public high schools, mentoring them, and paying their tuition for parochial school. That meant on Saturdays, I’d take the subway uptown, several stops past Harlem, to see Melissa, one of these students. We’d watch a movie or walk around Central Park, and I’d encourage her to stick with math, at which she excelled. After high school she enrolled in New York University, but later dropped out for financial reasons. I wish I hadn’t lost touch with her. I think about her often when I’m advocating for affordable college tuition or science and math education for girls.

  My own life, while tidy on the surface, was a bit of a mess underneath. Throughout my twenties and early thirties, I was always looking for a guy that I considered a catch. To me, that meant a man who was good-looking, athletic, smart, talented, promising, hardworking, or all of the above. My relationships tended to last four or five years and end in either disappointment or disaster. Some of the men I dated undermined my sense of self-worth, convincing me that I wasn’t smart, attractive, or interesting enough. One even became hostile and controlling. I needed to find a way out, which proved harder for me than I expected. I started worrying about myself. Friends and family grew concerned, too.

  Breaking my bad relationship patterns became a priority, and somewhat to my surprise, faith helped me a great deal. I started attending a weekly women’s Bible study class, and quickly grew to adore it. Once I started thinking more about faith, I began to see how lost I’d been. I needed to find a partner who was loving and kind. A man who would make me happy and would also allow me to thrive. Jonathan came along at the right moment. He’s handsome, charming, and sharp-minded, and he also exudes a thoughtful and genero
us kindness—the whole package. I was intrigued.

  After I’d canceled that first date (the gala with a group of ten, including some of Jonathan’s friends from Columbia Business School, where he was studying at the time), we finally had a proper one, and it was fantastic: brunch, followed by browsing in Barnes & Noble, then a walk, a trip to midtown to pick up some work (yes, romantic), the evening “singles” mass at church, dinner, and a stroll back home, ten hours after I’d left. I felt so happy and comfortable with Jonathan from that first day. He never made snide remarks. He never insinuated that I wasn’t entitled to an opinion. Never said that I wasn’t his type, or that I ran funny or that I needed to lose five pounds. It’s amazing how many strong, self-empowered women get caught up in bad relationships. I know you all know this, but believe me: You really do want to go for the nice guy, not the hot, flashy, or cool one.

  On Sundays, during those years of trying to sort out myself and my love life, I’d go to church. For six years I attended a progressive evangelical church—a bit odd, since I was raised Catholic, but I really liked the preacher. I also taught a Bible study class to ten-year-olds, and I joined the church community in volunteering to help those most in need, in part through the Little Sister Project, dedicated to assisting women who’d been prostitutes and in jail to integrate back into society. Raising money for the Little Sister Project was my first foray into fundraising, and I honestly enjoyed it. I didn’t expect this; all anybody ever says about fundraising is that it’s awful. But I was hooked when I realized that the money isn’t for you—it’s for creating a change that you believe in.

  The voice that motivated me to take my life in a new direction came from a woman in a pink suit. On September 5, 1995, Hillary Clinton, then still first lady, spoke at the Fourth World Conference on Women in Beijing, China. At that point, my work at the firm was not capturing my heart, and on that day, Hillary said her line about women’s rights being human rights, a line that I’ve repeated almost once a week for the past ten years. Her words were so simple, brave, and powerful, and when I heard them, something woke up in me. I cared about China. I’d majored in Asian studies and spent a semester there in college, devastated by the poverty and pollution but inspired by the culture and the strength of its people. I even spoke passable Mandarin. With her words, Hillary put me back in touch with my childhood dream. I needed to alter the course of my life and get involved in politics. That was who I was and who I had always wanted to be. It was time to embrace what mattered to me most and overcome my fear that others would disapprove of my ambition or view me as presumptuous or entitled.

  My family’s political world was all back in Albany, so I called a friend whose mother, Nancy Hoit, was active in politics nationally. When I called Nancy, she couldn’t have been nicer. She told me to join the New York City chapter of the Women’s Leadership Forum. The organization, in turn, said they’d be just thrilled if I joined. All I needed to do was write a check for $1,000.

  My first thought was “That’s a lot of money!” (My actual thought might have included some swearing.) I’d never written a check that large except to pay my rent. My salary as a single attorney was much more than I needed, but even so, I got a little anxious filling out the “Pay to the Order of …” line and the amount. But I did it. It was the one piece of advice I’d been given about getting involved in politics in New York City, so I took it.

  My grandmother Polly had taught me that, in politics, you do what’s needed. If a candidate you support needs an envelope stuffed, you stuff an envelope. If that candidate needs a breakfast hosted, you host a breakfast. When you believe in a cause, you aren’t picky; you just help. In New York City, I quickly learned that what candidates really needed help with was raising money. So that’s where I focused my energy. I liked the challenge—it wasn’t unlike selling Girl Scout cookies, piquing my competitive instincts by providing a measurable goal.

  My early days working in politics in New York City had none of the gritty charm and romance of a room full of Polly’s girls in their sleeveless shirts. But I threw myself into it. The Women’s Leadership Forum supports Democratic nominees for president. The women involved knew everything and everybody, or so it seemed to me. From them I learned why supporting candidates directly is crucial. Until that point in my adult life, I had never said, even to myself, “Politics is important to me.” Now I did, and it was one of those great young-adult epiphanies, an exhilarating moment of clarity when you stop traipsing down the path you’re following and discover the one you really want to be on. I didn’t run for Congress for ten more years. But that was the first step in defining where my life would go.

  As a direct result of writing that check, I found myself in 1995 listening to the first lady that day when she came to speak at the River Club. As I stood in the back of that ornate room, she said the line that woke me up and that I still repeat: “Decisions are being made every day in Washington, and if you are not part of those decisions, you might not like what they decide, and you’ll have no one to blame but yourself.”

  Those words cut through me. If I went into politics, I risked giving up financial stability, but I knew I couldn’t just keep volunteering: I had to figure out how to make public service my job. So I joined every board and political group I could, and I sought out political mentors.

  When you want to be taken seriously in politics, you have to prove you can deliver, often financially. But as I soon learned, getting people to write checks to a political organization or candidates isn’t nearly as easy as getting them to support, say, the Little Sister Project. Nine out of ten people don’t care much about politics, and the contributions aren’t tax deductible. I had to beg my Davis Polk friends to come to events, which they usually did just to be nice. (I think a lot of my friends still come to political events only to be kind to me.)

  Then, in 2000, Hillary Clinton declared she was running for Senate from New York. I was beyond excited. Here was this incredible woman who had influenced me so much, running to be my senator. I tried to get hired by her campaign office, but I didn’t get far. I had no experience, and I wasn’t all that well connected yet. The fundraising I’d done and the donations I’d made were very small ball. Jonathan, who by that point was my boyfriend, thought I should step up my contributions. “If you really love politics and want a future in it, then you really need to invest your money, too,” he said over dinner one night. I was making close to $200,000 a year, far more than I needed. So he suggested I increase my donation budget from $2,000 to $10,000 a year.

  The whole notion made me anxious. These days I’m constantly trying to get women more comfortable with political giving. A lot of women, myself included, give themselves license to spend money in ways that project their values if they are related to their family or their home. But that does not seem to translate to political action or supporting candidates. Men seem more comfortable spending money on a wider scale, often to project their power. We all know the cliché of the man buying the flashy car in the midlife crisis. In my experience, men write big checks to political candidates for similar reasons: to make themselves feel powerful.

  So I wrote another $1,000 check to attend a Hillary Clinton fundraiser at the beautiful Upper East Side home of Felice Axelrod, a major Hillary supporter. The apartment was elegant, filled with modern art and beautiful flowers. A new friend, Helen Cook, who’d worked on political campaigns for forty years, had suggested that I arrive early so I’d have a better chance of speaking with Hillary. So I put on my best gray wool suit and arrived at 5:15 P.M. instead of 5:30 P.M., joining a dozen other early birds nearly as enthusiastic and starstruck as myself. With a glass of red wine and an absurdly broad smile, I waited for my chance to talk to Hillary. When I reached her, I started gushing. “I’d love to do anything to help you. Really, I would just love to help in any way I can. It would be my pleasure. I’m so excited about your campaign.”

  “I’d love that,” Hillary said graciously. She clutched my hand for a mo
ment and then we were done, Hillary moving on to the next woman waiting in line. But I clung to our brief encounter. Next morning I called Hillary’s campaign headquarters to report to her staff that Hillary had told me, herself, that she would love my help. When this did not translate into anything besides a chance to make phone calls and stuff envelopes, I dipped back into my donation budget and spent another $1,000 to attend another Hillary fundraiser, this one at donor Charles Myers’s house in Tuxedo Park, about an hour from New York City.

  That time, when I reached the front of the reception line, I said to Hillary, “I followed up with your staff about helping, but they said there was nothing in particular they needed right now, so I’m just volunteering in the headquarters. But, truly, I’d love to help in any way I can. I’ll do whatever it takes to get you elected.”

  Hillary focused for a moment. “I would love you to do one thing,” she said. “I would love you to host a fundraiser with young women your age.”

  “Oh, I can do that!” I said. “I’ll get that done!”

  Hillary gave me her assistant’s card, and the next day, feeling triumphant, I called and announced, “The first lady said she wants me to host a fundraiser with young women my age, and I’m going to do this for her!”