Rachel E.Skiffer

This piece, giving us a glimpse into Rachel Skiffer’s life before she arrived at Head-Royce, was written by Head-Royce alumnus Cole Reynolds ’22, with editorial contributions from Jayanti S. ’23 and Charis W. ’23. Reynolds is in his first year at the Medill School of Journalism at Northwestern University.

SNAPSHOTS IN TIME WITH RACHEL E. SKIFFER

By Cole Reynolds ’22

Elliot Kirschner has this image of teenage Rachel Skiffer ingrained in his mind. Eyes closed, head thrown back, smile gleaming, she’s halfway through one of her distinctive laughs—one that her friends say comes so easily. To Kirschner, while the subject is clear, the rest of the image is a bit blurry. Time will do that. Sometimes when he recalls it, they’re driving Skiffer’s old Taurus station wagon through the Sunset District. Or through the Richmond District (always with music, likely a little Billy Joel, he adds). Other times it’s at a house party or during their classes at Lowell High School. Maybe, Kirschner suspects, the image is more of a mosaic—one pieced together from countless memories of Skiffer.

“She would always just be the center of our world and our conversations— pulling people together,” Kirschner says.

“Even then [back in high school], you could sense that this was a person that people relied on, that they trusted, that they went to in times of uncertainty.”

The traits Kirschner describes make Skiffer particularly suited for her new role as the 12th Head in the School’s history. In a way, Head-Royce came to her in a time of uncertainty. Still recovering from the pandemic and continuing to await approval on the South Campus construction project, the School finds itself in a new state of normal. And like her friends, HeadRoyce, too, benefits from Skiffer’s sharp eyes and fresh perspective.

According to Kirschner, that’s a strength of Skiffer’s. Even now, he fancies her a weaver of sorts, holding threads of knowledge spun from her personal experiences and education. Kirschner, now a journalist and filmmaker, still solicits Skiffer’s advice to contextualize the racial, gender-based and historical elements of his life’s work. And he is not the only one that seeks her input and candor. According to Kirschner, he is one of many. “She has this incredible network of people that she’s accumulated—that’s not the right verb—that she has...inspired.”

Capers And Mushrooms

Take Ariel Wilsey-Gopp. Her first image of Skiffer is on the playground at Katherine Delmar Burke School in San Francisco, Skiffer’s hometown. It’s of a 4th grade Skiffer blasting the ball out of the field during a game of kickball and watching it sail over the fence. “She had the hardest kick,” Wilsey-Gopp remembers. “She would get all the homeruns.”

And while her kickball skills were legendary, Wilsey-Gopp recounts many of Skiffer’s other admirable qualities. Some are the expected things: good grades, exemplary essays, lead roles in the school play. But what 4th grade Wilsey-Gopp especially remembered about 10-yearold Skiffer is that she liked capers and mushrooms. Whenever Skiffer was at Wilsey-Gopp’s house, she’d eat all of the foods in the refrigerator that Wilsey-Gopp found disgusting. “My parents thought that was so great. She was always getting compliments on how great she was from my family,” Wilsey-Gopp says. “She definitely excelled at everything.” Even when eating “grown up” foods, it seems.

Benji

Skiffer’s family was—in many ways—the impetus for her success. Her maternal grandmother grew up in Jim Crow Mississippi. And while she was privileged to have access to an accredited high school education that most Blacks were not afforded in the 1930s, it was still at a segregated school in her town.

As Skiffer’s grandmother made her way to Chicago during the Great Migration, she never forgot that Mississippi school— passing along her family’s legacy of respect for education as a pathway to self-determination. She made it a point to take a young Skiffer to visit one of the old teachers from that high school who lived in Chicago. Skiffer approaches education with a reverence shaped by her family history.

While her grandmother helped instill the importance of education in young Skiffer, it was her parents that safeguarded her educational experience as a Black child in a predominantly white elementary school. Skiffer thinks of her parents’ help as “running interference.” Like the time when her first grade teacher refused to let her check out the book “Benji” from the school library unless she read a portion out loud. Skiffer read with her finger underlining the words across the page while she said them, as she had been taught by the teacher. The teacher said that was evidence she wasn’t a good enough reader to understand a chapter book like “Benji.”

That evening, Skiffer casually told her parents what happened. And the next

Rachel as a young baby with her parents morning, “Benji” was sitting on her desk. Skiffer came to realize that in her younger years her parents walked up the steps of her school many times to advocate on her behalf and right unjust wrongs. She is now a proud member of the school’s Board of Trustees

Destructo

Skiffer’s success continued in high school. She and Kirschner were well-liked and surrounded by friends, Wilsey-Gopp says. They received the lead roles in plays, were the presidents of clubs and the students in AP classes.

Wilsey-Gopp wasn’t. “I was kind of a dork,” she says. Still, Skiffer made sure to keep up with Wilsey-Gopp, whether through a “How’s it going?” in the hallway or a laugh in the classroom. But most of their friendship was sustained through the soccer team. Neither Skiffer nor Wilsey-Gopp have particularly nice words to describe the experience as a whole. “My high school was the place that Title IX forgot,” Skiffer says. “We trained with the boys and only played against middle school teams.”

Skiffer came to realize that in her younger years her parents walked up the steps of her school many times to advocate on her behalf and right unjust wrongs. She is now a proud member of the school’s Board.

Wilsey-Gopp remembers the coach, an intimidating, European man. “He was so gruff,” she says. While they played, the coach would hurl a slew of insults at the players—to the point where other teams would stop and stare in shock. But for WilseyGopp, Skiffer was the antidote to that stream of profanity. “Her place on the team was one of team spirit and camaraderie,” she says. “Kind of like weaving and bringing people together. She would do that on the team.”

Although Wilsey-Gopp swears Skiffer had the hardest kick, Skiffer nicknamed Wilsey-Gopp “Destructo Leg.” So whenever the ball rolled towards Wilsey-Gopp, Skiffer would scream “DESTRUCTO!” as Wilsey-Gopp blasted the ball forwards. “It was endearing,” she remembers. “It was like an anthem.”

There’s one last image that Wilsey-Gopp has of Skiffer in high school. Registering for classes at San Francisco’s Lowell High School was a disaster. Students were lined up outside the gym in alphabetical order, with teachers inside waiting to register them for classes. “Ready, set, go,” would ring through the air. The doors would swing open. The students would stampede in.

Harvard Law Drama Society with Tori Jueds to Rachel’s right in the front row

Wilsey-Gopp can picture Skiffer sprinting up the line—her hands grasping pencils, her long strides weaving through the sea of people. She might have invented this image, Wilsey-Gopp concedes. Still, her association of Skiffer with confidence and self-assuredness remains, qualities that would serve Skiffer well throughout her life…but not without plenty of humor sprinkled in.

Laughter

Tori Jueds met Skiffer because of a shared laugh. It was Jueds’ first year at Harvard Law School and Skiffer’s second. They were backstage at Harvard Law’s drama association production. And by chance, they locked eyes and burst into a fit of laughter. Nobody else joined them. The moment was theirs alone.

In many ways, laughter charted their way through law school. They were a writing team on Harvard Law’s SNL-like comedy show, “The Parody,” creating satirical verses for Def Leppard and Britney Spears songs, among other projects. There’s this pressure permeating Harvard Law, and its storied past weighed down upon Jueds’ shoulders during her time there. Her laughter with Skiffer was a respite from that. “It’s necessary for everyone to remind ourselves that we’re all ridiculous. None of us have figured it all out,” Jueds explains.

That relief was especially important for Jueds, who never really wanted to be a lawyer. She’d been an activist for reproductive rights and wanted a Juris Doctor to launch an activist career. To an extent, Skiffer wasn’t set on becoming a lawyer, either. “I treated law school like grad school,” she says. Skiffer decided to go to law school because of her undergraduate experience. In college, she did as much as she could, from economics classes and creating her own Women’s Studies major, to joining the Harvard University choir and acting in a theater production with Rashida Jones (an actress best known for her role on the show, “Parks and Recreation”).

However, one thing from her college experience jumps out in particular: her. “It really illustrated powerfully to me this talent of Rachel’s, to connect with fascinating, excellent, wonderful people and to nurture those friendships over many years,” Jueds says.

A few years after she graduated from Harvard Law, Jueds needed that friendship. She had just lost her dad. Skiffer has this phrase: “fly out moment.”

It’s for the times when a friend of hers is thrust into vulnerability. And it describes her reaction to them: to drop everything and fly out to their city. So when Jueds’ dad passed away, Skiffer was on the next flight to New Jersey.

It’s been a long time, so Jueds can’t remember the exact conversations they had once Skiffer landed. But she remembers it being like talking to a mirror—that Skiffer could connect with her and support her so intimately. “Those were the sorts of times when just the presence of a really good, soulmate- level friend means more than anything,” Jueds says. “And Rachel has been able to provide that a number of times.”

For Kirschner, it’s these complexities, these vulnerabilities in Skiffer’s story that make her advice the most useful and her shoulder the easiest to cry on. “Life isn’t simple,” he says. “She really understands that, and she’s able to help you navigate through that.”

Searching

Skiffer and Jueds graduated law school when consulting firms— lacking business school graduates who were flocking westward towards Silicon-coated fortunes in Palo Alto— were forced to turn their attention towards other highly-educated professionals. And McKinsey & Company snatched up Skiffer.

Skiffer talks about the skills she acquired at McKinsey—how she learned to use Excel and what a PowerPoint was. But she reflects on those days with an uncharacteristic dullness. Except, of course, when she mentions the day her colleague walked away from that same high-paying McKinsey job to work the floor at Sephora in preparation for founding a cosmetics company. “That was brave,” Skiffer laughs.

A week after her colleague left, Skiffer considered leaving McKinsey, too. At a college football game, she met an old friend who worked in the Harvard Admissions Office. That friend later lent her (perhaps “illegally”) some applications to read. Skiffer was hooked, poring over every word of these students’ lives—getting to know people she’d never meet.

a life-changing class on the Warren court. Through the class, she gained a “window into [her] history as an African American.” Education was one of her family’s key values and in that class, Skiffer got the chance to learn more about just how hard others fought to obtain it. And so, Skiffer’s decision to go to law school—like Jueds’ as well—wasn’t about training for the bar exam. It was for choosing niche classes and finding new knowledge.

FLY-OUT MOMENT

Knowledge wasn’t the only thing Skiffer gained during her educational journey. She also created an array of lifelong friendships.

For one special occasion, Jueds came up with the idea of a scrapbook filled with pictures and memories and words from everyone floating in Skiffer’s orbit. What she didn’t envision, however, is the magnitude of people who would contribute. What resulted were pages of people, some who had shared monkey bars or a slide with Skiffer; others who had shared an office or classroom with

Receiving a blessing from Pope John Paul II

Skiffer couldn’t shake the feeling that she was being called to the world of education. The stories of students beckoned her toward the field. So when that friend called her a few months later, letting her know about a permanent spot in the Harvard Admissions Office, she remembered her old colleague who was now working for Sephora when she responded. “Yes. Yes, I’ll go for it,” she said back into the phone.

Skiffer knew she had landed in a career that she loved—one perhaps inspired by her grandmother, who had instilled in her the value of education so long ago. And yet the timing wasn’t right. After a few years, student loans kept calling, forcing Skiffer from the ethereality of that Harvard Admissions job into the slog of commercial real estate law. On one hand, it was a continuation of family legacy— Skiffer’s mother was a city planner and her father was a commercial real estate developer. On the other, “My heart just wasn’t in it,” she says.

And so Wilsey-Gopp has one more image of Skiffer that stands out from the rest. She found herself sitting in the passenger seat of Skiffer’s car, talking about work. They’d pulled in front of a convenience store on top of a hill overlooking San Francisco.

Skiffer cut a defeated figure against the backdrop of sunlight blistering through the windshield. “I’m just so tired of this,” Wilsey-Gopp recalls her saying about her job. And what Wilsey-Gopp remembers most is how different that Rachel Skiffer looked from the Rachel in her mind—the one sprinting through hordes of students to register for the class she wanted.

“When people are so driven, and they always know what they’re doing— what they want,” Wilsey-Gopp says, her voice trailing off. “It’s rare to see them in these moments, not quite knowing what’s next. And so it stood out for me.” But as soon as it came, the moment was over. Perhaps Skiffer didn’t know what she needed from her career, but she knew she needed groceries for that night. So, they sped towards the supermarket and away from that ever-so-evanescent moment of uncertainty and vulnerability.

Skiffer had endured a much more prolonged period of vulnerability before, though. Her mother was supposed to have a routine hysterectomy. But after complications, Skiffer’s mother passed away from the surgery. Skiffer was only 19. The suddenness of it shrouds much of the moment in haze. It’s still difficult for Skiffer to talk about. She makes a lap around her office in search of tissues before she recounts the story. But it is still one that she shares. The funeral was a couple of days later. Legions of former teachers and classmates filled the pews, in support of Skiffer. The service is a bit of a blur, but Skiffer still remembers a distinct feeling sitting in the church. “I just felt so held,” she says, pulling out a tiny bottle of eyedrops from her bag. “And I just feel the need to pay that forward.”

At Home

There’s this panorama as you drive down Lincoln Avenue. Flashing through the tree branches are glimpses of the jagged San Francisco skyline, grasped by the Bay’s morning fog. Somewhere in those mess of buildings is where Skiffer grew up—had “Benji” placed on her desk and dominated kickball. Her brother still lives in the area, too, also in education as the Urban School’s Athletic Director and varsity basketball coach. Skiffer’s circuitous path to becoming the Head of School gives her the skills to excel in the position. Law school gave her pedagogical knowledge and real-estate gave her an understanding of business. Her time in education—as an admissions officer and student, a dean at one of the oldest American boarding schools and the leader of Sal Khan’s start-up K-12 in Silicon Valley—gave her the background she needs to run the School. Skiffer is here to give Head-Royce something she has provided on every one of her travels: a listening ear, curiosity about each community member’s story and a care for the people around her.

Vangeria Harvey, co-chair on the Head of School Search Committee, raved about Skiffer’s positive qualities, “We wanted someone that was collaborative, thoughtful and just had a care for young people and a love of education.”

Harvey also appreciated Skiffer’s commitment to diversity, equity and inclusion (DEI). “She rejected the tension of DEI and academic excellence—because you can’t have one without the other,” recalls Harvey.

While Skiffer brings her vast array to the School, she is getting something back in return: a destination, both as an educator and as a person.

Skiffer was drawn to Head-Royce because of its location in Oakland. Her godparents lived here, and she remembers spending holidays at Fairyland. When she had kids of her own, everything came full circle. Even while living in the South Bay, she took her kids on “pilgrimages” to Fairyland, Lake Merritt, Oakland Museum of California (OMCA) and jazz shows at Yoshi’s. “I wanted them to soak up the diversity of Oakland,” she explains.

Skiffer chose Head-Royce partially because of its reputation in the Bay Area. Her godbrother attended for eight years, and she’d visited campus for numerous faculty development programs over the years. “The faculty here are held in high esteem within the Bay Area,” she claims. And Skiffer wanted to be a part of that. She still remembers the history lecture on indentured servitude that she sat in on when she first applied to be the Head of School. She recalls being impressed by both the teaching and the questions the students asked. She had found her passion for lifelong learning reflected by the school community.

“I remember walking here on my first day,” Skiffer says, her eyes wistfully drifting to the top corner of the room. “It just kind of felt like home.” And so it is. With a scrapbook full of people who trusted and relied on her wise counsel, fresh perspective and grounding in times of uncertainty, Skiffer is well-equipped to lead HeadRoyce into the next phase of growth.

“In some way, it feels like my entire career has led me to this place, to this position,” Skiffer says. “With the South Campus construction project on the horizon, Head-Royce represents the culmination of every role I’ve held to date. I’ve never felt more certain that all my travels have brought me here…and I hope to stay for as long as the School will have me. I have a kindergartener, after all!”