My parents were 26 when I was born—1976—and I just remember them rolling with life. Memories are faulty, sure, but my mom and pop tell stories about going out when they were dating, and it just sounds so nice. They would eat Chinese takeout and watch All in the Family and M*A*S*H and take Opie’s car to get gas during the 1973 oil crisis. See? Simple. Pleasant. Fun. You ate what you were given. There were no designer menus. There was no worrying about whether your kale or your tampons were organic. My dad used to let me help make meatballs—two years old and just crushing some raw meat with my bare hands. I’m not sure how many parents would let their kids do that now, but it was so fun, and I survived. There are more than a few photos of me sneaking the last sip out of a beer bottle.
I don’t want to give you a “when I was your age” speech—I like organic kale, I invest in an organic tampon company because I believe they truly are life-changing, and I often order lunch through Seamless, which is maybe the complete opposite of “You ate what you were given.” Today, we have many more choices, and while these choices allow us a freedom I could never have imagined growing up in tiny Rhinebeck, they also make it easier to veer off course.
To be fair, I had a lot going for me. Until my sister was born, I was the only granddaughter on either side of my family, and I got a lot of attention. But I don’t remember seeing things other people had and wanting them. I remember specific moments when I just felt content, and I still am. I think that even at a young age, I had a sense that life was what you make of it. That, and the confidence that jelly donuts are about the best thing on Earth. The two things are probably related; if a $1 jelly donut makes you really, really happy, you can get through a lot with a little.
If I’d had parents whose goal for me was to be successful—to be a doctor or a lawyer or a CEO—I probably never would have ended up where I did. It’s also safe to say that if I had woken up one day during high school and said, “Mom, I figured it out. I want to be deputy chief of staff for the president! I think I can swing it by the time I turn thirty-five. What’s for dinner?” I wouldn’t have ended up there either.
I was the first woman to occupy the physical office whose previous inhabitants included George Stephanopoulos, Rahm Emanuel, Karl Rove, David Axelrod, and David Plouffe. That might mean something to you, or it might not mean anything at all. It’s not exactly the kind of job six-year-olds are naming for the “What do you want to be when you grow up?” question. It’s not even the kind of job precocious 26-year-olds are gunning for. Most people who hear the title don’t really know what I did. (Though they know enough to be impressed—especially if you say it kind of loudly, while raising your eyebrows and making a big gesture.) Jobs like this—the kind of job of which there are many, the kind that are definitely good but that no one teaches you to want—are found only with an open mind and a willingness to do your own thing.
One of my biggest advantages is that I was raised to be independent. (Not having Google around to answer any question that might have occurred to me helped.) My pop put himself through college stocking shelves in a liquor warehouse. My mom went to fashion school, worked until the day before she went into labor with me, and saved enough money from her job to buy our first house. A story I grew up hearing about my Omie is that after spending time helping Jews leave Germany before the war, she fled the country—her home—by herself, traveling through Switzerland and the UK with only my uncle Dieter, who was a baby at the time. One of the few possessions she had with her was a set of aquamarines; she hid them in his diaper. These are good role models.
Here’s a childhood anecdote that is kind of corny but very useful in constructing a metaphor: I was probably two or three years old, and Omie, my mom, and I were at the 44 Plaza shopping center in Poughkeepsie around the holidays. We had just parked the Chevy Malibu and were crossing the parking lot to the Hallmark store when my grandma told me, “Schatzi, hold Omie’s hand.”
“No, Omie!” I said. “I hold my own hand!”
She promptly grabbed me by the hood, but I did hold my own hand.
It’s kind of like life, right? We start by holding our own hands, kind of knowing someone has got us by the hood. I later tried to touch some crystal ornaments in the Hallmark store, and the hand I was holding myself with was smacked—an apt illustration of how independence can get you in trouble sometimes. (I never touched crystal ornaments at Hallmark ever again.)
Things were cruising until my sister Moosie was born. Moosie’s real name is Lauren, but one Sunday morning when my pop was testing me on my middle-school French vocabulary, he pointed to a grapefruit on the table. Lauren was walking down the stairs as I said pamplemousse, and she replied, “I am not a plump little moose!” She is 36 years old now and still Moose.
But back to 1980. I don’t really remember my mom being pregnant or the fact that she was having a baby. I do remember the night she went into labor: We packed up the car and Mom and Pop dropped me off at Mrs. Endsley’s house. Kimmie Endsley was my best friend, and her older sister, Kristen, was really cool. I got to try Lucky Charms for the first time. (At 19 Vincent Road we had only Cheerios and Rice Krispies.) These were the true benefits to having a little sister!
When my mom called to say Moose had arrived, Mrs. Endsley asked me if I wanted to talk to her. I really didn’t want to. Kimmie and I were having so much fun! But I did. I heard I had a sister.
I also heard that Omie and Opie were driving up from New Jersey. JACKPOT AGAIN. Omie brought me a tea set as a present for becoming a big sister. We washed the drapes. It was the best.
Then Moose came home. Even when I was four, I knew she was cute—big cheeks, bigger thighs, and a huge head. She was really tan. All of this annoyed me. Her room was painted yellow, which annoyed me more, because my room was white, which seemed, at the time, objectively worse. (Looking back, her room was basically mustard yellow, so I don’t know why I cared.) I did not want to hang out with her—I was with Omie, in the way that you are with people when you’re young. I was very possessive, which was OK, because I was four years old, and although I had my independent streak, I didn’t understand that the grown-ups had lives and preferences and friends they occasionally met up with for lunch or a walk (or some wine). I was the favorite, and I had to continue to be the favorite. Moose had only been around for a few days and really only pooped!
A little while after she was born, I think this attitude was showing. I remember brushing my teeth on my stepstool—it read, “To sit / To stand / This stool is really grand”—and I had a ponytail. My mom came in, gently grabbed my ponytail, and said, “This attitude ends today.” After that, I tried to think about—at age four—the upside of being a big sister. Maybe there were perks? Maybe this was someone who would be required by blood to always think I was cooler and smarter?
Um, not the case. Moosie turned out to be taller, thinner, and a terrific dancer who always won awards. She was also a little aggressive. When she would get mad, she would roll down the hall in her walker and bite my bed. She liked to eat dirt from the houseplants and carry around a small bottle of bourbon (unopened). Her claim to fame was being called out at Freedom Plains Nursery School for getting on a tricycle and plowing through a castle some kid had built. You really never want her mad at you—she’ll just stop talking to you.
(Now, Moosie and I talk almost every day. She can tell when I’m upset by how I punctuate my text messages and is always quick to suggest a mani-pedi or some Shake Shack to lift my spirits. When she got married, I toiled for two weeks to make my homemade granola and thyme-roasted marcona almonds as favors for all the guests.)
Being the oldest, as any oldest would attest, is a lot like being a pioneer. My first day of kindergarten was eye-opening, a wonder. Kindergarten was where I realized that, aside from the occasional “good girl Twinkie,” we ate really healthily in my house. There was a much more exciting culinary world out there.
I liked school a lot, and I loved to read. I read way ahead of my grade level, but my
mom never censored my books. I loved Judy Blume, and I think 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?
Around first grade, I wanted to join Girl Scouts, so I became a Brownie. This may have been the very first time I noticed a theme in my life that would go on to fail me again and again: Everyone was doing it, so I wanted to try, too.
Back in the early ’80s, getting promoted to Girl Scout wasn’t just about being old enough—you had to sell enough cookies. When the time came to sell those damn things, my mom made it clear she wasn’t going to lift a finger, aside from buying the Thin Mints, Samoas, and Tagalongs we would have bought anyway. She wasn’t going to pimp my cookies for me. Not like our dance instructor—let’s call her Barb—who would put her daughter’s order form at the door so parents could fill it out. Once the cookies arrived for distribution, Barb’s dance studio looked like a Girl Scout Costco—Do-si-dos were flying everywhere. (Peanut allergy awareness was much lower than it is today.)
I, however, was on my own. For all the talents I may claim to have, sales is not one of them. Even today, I cannot stand fund-raising or asking people for things. I didn’t make these cookies. What did I really care if I didn’t sell them?
Mom and Pop got me a walkie-talkie and sent me up and down Vincent Road, the gospel of Thin Mints playing on repeat in my brain—you can keep them in the freezer and save them for months!—as if I were not a five-year-old kid but a stressed-out mother of two looking to streamline her cookie storage processes. I was not good. I was quite bad. We lived in a neighborhood with lots of Girl Scouts, making competition stiff and plentiful, but that wasn’t really my problem. No, my approach was flawed: I mostly stood at a lot of front doors without ringing the bell.
I never made it to Girl Scout. When it was time to congratulate all the girls in my troop for selling exemplary numbers of cookies, I got a little award that was different from everyone else’s.
This experience, while inducing a tear or two from five-year-old me, was beneficial: It taught me that failure was survivable, that it wouldn’t ruin my life. (It helped, of course, that my mom did buy those few boxes, which I snacked from to console myself.) I failed on my own. I didn’t think Barb’s daughter was such a genius—her mom did all her work! I also learned at a young age that I was not, and never would be, a saleswoman. An easy thing to cross off the list of potential futures.
Over the years, my parents let me hold my own hand a lot. I think they always just hoped my sister and I would turn out to be good people—they didn’t care about how successful or prominent or wealthy we would be. For example: dance classes, the extracurricular of choice (or parental pressure) for countless young girls, no matter your generational era. I took tap, ballet, and jazz for almost 12 years, and what I lacked in natural ability, I made up for in enthusiasm. I rationalized that I danced in the wings at our finales because of my height. I assumed that if I was sweating, I was succeeding.
Moosie, though, was a killer. A really great dancer. As I got older, I realized—partially because I could see an example of someone who was so suited to dance, unlike me—that I was investing a lot of time, hours and hours each week, in something I wasn’t that good at and not enjoying all that much. It actually made me feel bad. I never had a solo.
I was 16 when I finally told my mom I wanted to quit. Although quitting is a thing many people now are taught to never, ever do, she didn’t flip out. She didn’t lose her mind or berate me about having extracurriculars on my college applications or say I had been dancing for so long that I should keep going. She said it was OK. If you do it responsibly, quitting something that isn’t benefiting you—whether it’s dance classes that “everyone is taking” or a soul-sucking job that has nothing to do with anything you’re interested in—can change your life.
After I finished dance, I didn’t sit around eating Now and Laters and cruising the highways and byways of Rhinebeck. I was first flute in the band in school. I took French. I babysat for a family down the street every Saturday night, and I also worked at their anemone barn. I would wrap the flowers in wet paper towels and newspapers to prepare them for long trips back to the city with tourists every Sunday. This wasn’t some bougie “barn”—it was an actual barn, with power tools and a tiny space heater. My best friend, Cara, visited me every weekend and brought me soup or donuts or a bagel. I loved it there.
I also had a job as a checker at Kilmer’s IGA Market, a grocery store in the center of town. Anyone who has worked at Kmart or Walmart or their own local grocery store may not believe me when I say this, but I really liked it. Sure, some days you definitely want to hang with your friends instead, but I was good at bagging groceries, and it meant I could afford tickets to see Phish or God Street Wine or the Dead. I could buy crystals—they were cool then, too—and smock dresses from Winter Sun.
I also learned a lot about people. What they bought. Who used coupons and who didn’t. Who helped you pack and who just stood there and waited. Who watched you scan every item and questioned the price.
Our store was one of only a few that accepted food stamps in the area, which gave me more perspective than almost anything else I experienced growing up. It’s a moment when you see a woman with a kid, or an older person, trying to figure out what the food stamps cover. The humiliation they can endure while holding up the line, or having to put things back. It forever formed my opinion on how we should help those in need: humanely and respectfully. Maybe that sounds obvious to you, but unfortunately there are a lot of people who would disagree.
Years later, we were having a discussion about food stamps in the White House. My job was never policy focused; I scheduled and coordinated and planned, dealing with times and dates as well as with personalities. But I often sat in on policy meetings so that I could understand our priorities and be able to use my judgment as my team decided, out of a hundred different choices per day, how best to use POTUS’s time. This discussion was a follow-up to a conversation Obama had had with someone else; often he’d gather senior staff to talk over issues as a group after meeting with a particular person.
Because of the economic recession, there were a lot of people on food stamps at the beginning of Obama’s presidency. That number dropped over his term, but we didn’t only have meetings about what was happening right at that moment, because if you’re just dealing with things as they’re happening, you aren’t prepared for something to come out of the blue. This meeting was in the Roosevelt Room, but I wasn’t sitting at the table—I was sitting along the wall. Seating is surprisingly limited in the West Wing—the chairs are huge and not that many fit around the conference tables, many of which are historical or have some other kind of significance, so invitations to meetings are kind of exclusive. Everyone in the room needs to have a good reason for being there.
From the beginning of my career in politics, I had a personally imposed policy about swimming in my lane and not overcommenting on things I wasn’t an expert on. But in this case, 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. I could feel my face get red and hot. I usually think you start losing your argument when you physically reveal how worked up you are, especially in a plac
e like the White House, where, theoretically, what you say should be based on facts and figures and evidence; if your face is red, aren’t you showing too much emotion? I don’t know, but I got my point across. It wasn’t a conversation intended to resolve or change anything at that moment, but POTUS made it clear he was on my side.
The best part about those jobs in high school—all of which I gained some satisfaction from and remember fondly, even if at the time I was thinking I would rather be watching 90210—was that they taught me a very important way to rationalize when my career seemed doomed or my life felt like it was veering totally off course: If I am never good at anything else, I know I am good at this. You might think that sounds depressing, but it’s given me a lot of comfort over the years. There is no greater feeling of independence than being able to provide for yourself, knowing that if you really hate a job—and you will probably hate jobs at various points throughout your life—you can leave and be OK.
When it came time for me to apply to college, I had one of those moments where I needed to remember that, at the end of the day, at least I was really good at bagging groceries. That if I didn’t get into Harvard (or even choose to apply), I would end up where I was supposed to end up.
The time period was 1992–94; there was no email, no Internet. We drove to Barnes & Noble and bought the US News college guidebook. Cara and I spent hours and hours tagging pages and talking about where we wanted to go. I underlined addresses and, in the summer before my senior year, wrote away to request applications.
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