CHOATE’S TEACHING EXCELLENCE SERIES
BULLETIN FALL ’23 | WINTER ’24 | SPRING ’24
Connecting Alumni in the Classroom
by susanne Davis
Photo credit: Foster Wiley
The soul-shifting experience of inspiration often precedes human advancements and drives us forward to new levels of achievement.
At Choate, teachers engage students in the deep inquiry associated with inspiration to create this kind of transformational learning. Choate’s academic environment provides dynamic engagement with texts, collaborative learning, and individual inquiry. But, on occasion, the School goes one step further to add to the alchemy — connecting alumni to students’ learning.
This academic year, the Bulletin offers a series to look at how teaching happens here, peering through the lens and stories of three inspiring alumni to see past, present, and future.
Featured in this issue, two-time Pulitzer Prize winning former New York Times reporter and Emmy award-winning producer and correspondent Hedrick Smith ’51; in winter, cybersecurity expert and technology visionary, Window Snyder ’93; in spring 2024, Diversity, Equity & Inclusion expert Natalie Egan ’96. Through their stories and experiences back on campus, they contribute to and help highlight the extraordinary teaching at Choate.
HEDRICK SMITH:
PAYING ATTENTION TO HISTORY
For 70 years, Hedrick “Rick” Smith’s formidable reporting skills have taken him all over the world. In 26 years with The New York Times, Smith covered Martin Luther King Jr. and the civil rights struggle, the Vietnam War in Saigon, the Middle East conflict from Cairo, the Cold War from both Moscow and Washington, and six American presidents and their administrations. In 1971, as chief diplomatic correspondent, he was a member of the Pulitzer Prize-winning team that produced the Pentagon Papers series. In 1974, he won the Pulitzer Prize for International Reporting from Russia and Eastern Europe. His 2012 book Who Stole the American Dream? was hailed by critics. He is at work on a new book about the story of our times.
As a student at Choate, Smith was Editor in Chief of The Choate News
Of the many groups Hedrick “Rick” Smith belonged to at Choate, he served on The Choate News board from 1947-1950, and was president of the board from 1950-1951.
He remembers the moment he felt inspired to follow his path. “It happened at Choate,” Smith says. “In a history class taught by Burge (C. Burgess) Ayres ’38. Burge knew I was running The News and he suggested I look at the muckrakers (reform-minded journalists of the Progressive Era of the U.S., 1890s–1920s). Lincoln Steffens, Ray Baker, Ida Tarbell, and William Allen White immediately became heroes of mine. What inspired me was that they were not just out to show the criminality of political corruption, they were looking at systemic issues of labor suppression, of economic corruption, of unfair trusts.”
Smith’s curiosity about how systems work and how they fail has driven his reporting throughout his entire professional life. “What is communism like? What works? What doesn’t? What can we learn from what works and what doesn’t?” He has applied that same kind of systemic questioning to American politics and to the economy, as well. “I’m looking for the big picture through concrete examples.”
By covering stories this way, Smith explains, his education has gone on forever. “Curiosity drives me.” There is no question in his mind that the suggestion from Ayres to read about the muckrakers was a major influence shaping him — “the idea that journalism can make our country and our politics better.”
Smith’s return to Choate last spring marked his first time back to campus since accepting the Alumni Seal Prize in 1981. “I was thrilled that the School asked me. I’d had the fun of interacting with the JFK (John F. Kennedy Program in Government and Public Service) kids in Washington. I was impressed with the caliber of questions, the curiosity, and their savvy.”
Head of Student and Academic Life Jenny Karlen Elliott saw how many students lined up to talk to Smith during that Washington trip and invited him to campus. She had to revise the itinerary — it wasn’t full enough, he said — to include three class visits, a meeting with The Choate News staff, lunch and a later afternoon drop-in for any interested students, a walking tour with Head of School Alex D. Curtis, and a dinner with the JFK Program students.
TOP Hedrick Smith’s The Brief Choate yearbook photo from 1951 MIDDLE Yearbook photo of the Honor Committee. Front row, left to right: Hedrick L. Smith, Herbert P. Ladds Jr., Gary E. Leinbach, and W. Roberts Wood Jr. Second row, left to right: James R. Bartsch, Joseph T. Consolino, Robert C. Leinbach, Archibald L. Gillies, William W. Pitkin, and Paul Draper.
BOTTOM/RIGHT Hedrick Smith visits classes.
STUDENTS ARGUE MOCK SUPREME COURT CASE INVOLVING SMITH AND THE NEW YORK TIMES
When Smith visited Ned Gallagher’s Constitutional Law class, students were arguing two Supreme Court cases, The New York Times Co. v. United States (Pentagon Papers case) and United States v. Caldwell. Smith had been involved in the NYT v. U.S. case and knew the reporter involved with the Caldwell case.
“I couldn’t believe it was high school kids arguing those cases,” Smith says. “They gave sophisticated, college-level argumentation, and it was thrilling.”
At Choate, the upper-level history class is popular with students. The first half of the term covers an overview and the major themes of constitutional law from 1787 to 1937; the second half is designed as a mock court covering three dozen landmark Supreme Court cases. Gallagher explained that each student in the class is assigned to a case — to write briefs and summarize the case; the rest of the class reads the briefs and hears the oral argument.
Teaching reaches a “quality engagement” for Gallagher when kids talk to each other and listen to each other. “What I do is set up a situation and prepare kids, so their contributions are high level. In the second half of the Constitutional Law course the kids take over.” Gallagher says he’s
always been a political junkie. “But truly, I’m standing on the shoulders of giants. I give full credit to the colleagues who preceded me.”
“What Hedrick Smith contributed that day was incredible,” Gallagher adds. “New York Times v. U.S. was a milestone freedom of the press case, and he was part of it. He knew both cases, and the people involved.”
Julen Payne ’24, a student in the class says, “That day was special. Mr. Smith went into depth about the cases; they were pertinent to him. He gave us a firsthand view of history. You don’t really get to see the people involved in historical events, but that’s what is special about Choate. Choate alumni are those people.”
Regarding Smith’s comments on the caliber of student presentations, Payne muses, “That’s only possible with kids who are at that level. Putting kids in the shoes of lawyers and justices allows us to get new perspectives. We’re learning history, but we’re also pretending to be part of history. Teachers here make the way they teach really unique.”
Payne’s focus of study is economics, not history, but he appreciates being able to “take interesting classes.” His learning extends beyond the micro and macroeconomics he says other high schools offer; this year he plans to take Developmental Economics, International Economics, and Behavioral Theories. “We’re allowed to go deeply into something. There’s always another rabbit hole to go down to pursue our passions. We never hit the floor at Choate.”
IN ANOTHER CLASS, STUDENTS
DISCUSS SMITH’S DRAFT BOOK CHAPTERS ON VIETNAM
In Jenny Elliott’s The U.S. in Vietnam (1961–1995), students read in advance two draft chapters of Smith’s book-in-progress, and came to class with typed responses, prepared to talk about it with him.
“The students were honored that Hedrick wanted their opinions,” Elliott says, “The chapters he shared dealt with his coverage of the Vietnam War and reflections about its long-term implications. It was perfect for what we’d been studying.”
“What the students in Jenny Elliott’s class shared as responses to the material was more personal than in Ned Gallagher’s class, they asked smart questions, and they were at a level of civic engagement that I couldn’t believe. That’s partly a sign of the times,” Smith says, “but also a credit to Choate.”
The students’ questions to Smith included:
“How did reading the Pentagon Papers change your view of government?”
It didn’t, Smith answered, because his view had already changed. “The sergeants and majors in the field in Vietnam were already telling us reporters that the U.S. was losing the war, contrary to what the government was telling the American people.”
“What impact did the publishing of the Pentagon Papers have on American public opinion?”
Smith painted a picture for students. “By 1971, tens of thousands of guys your age had burned their draft cards. I was at Harvard in 1969 to 1970 and the campus was aflame. Nationwide, the public was fiercely divided over the war. The long-term effect was an erosion of trust that the American people felt about our government.
“The Pentagon Papers were a watershed. They had an ever-larger impact on that erosion of trust in government, than on the conduct of the Vietnam War, and sadly, the erosion of trust has continued to this day. We need to understand our history better — for example, to see the longterm consequences of our mistakes in Vietnam, because what we don’t understand, we’re likely to repeat.”
WAKING STUDENTS UP.
“IT’S YOUR LIFE,” SMITH TELLS THEM
Smith’s 2012 book Who Stole the American Dream? analyzed how, over four decades, our nation became two Americas with growing economic inequality, the super-rich 1 percent vs. the 99 percent, and the rise of political polarization and the political tactics of dark money, gerrymandering, and vote suppression. In Jonas Akins’ Democracy, Media, and Politics class Smith urged students to pay attention “because these issues will affect your lives.”
He provoked a conversation designed to wake them up to their own power and stressed the importance of their civic engagement to their personal futures and the country. “I’m trying to shake you up,” Smith told students. “There are all kinds of things going on in our system with people and parties trying to ensure a lock on power. To take our democracy back, we need your participation.”
Hedrick Smith pauses for a photo with Alex D. Curtis and Jenny Karlen Elliott.
Photo credit: Susan Zox
When he asked students their impressions of democracy and one answered, “Democracy can be skewed based on wealth, power, and access,” Smith shot back, “Money is how it’s played. But what kind of money?”
“Dark money,” the student replied.
“But why does dark money matter?” Smith pressed. “Because politicians don’t want the public to see whom they are getting money from. They are hiding that connection,” he said.
As the conversation progressed into the issue of political polarization, students asked, “Do you hold media responsible for any of this?”
“Absolutely,” Smith said. “I hold the media responsible for a major role in the polarization of politics which makes them unworkable. By highlighting conflict and extreme opinions, the media is making this a much less governable country.”
He pointed to the different impact of social media from traditional media and the laws governing them both. “If you say it in The New York Times, or on PBS, it has to be true, or you can be sued. There is no libel law that applies to Facebook, Twitter, TikTok, nor Instagram. Algorithms drive their sites. These entities have no legal incentive to be honest. Congress passed a law that exempts them. That law should be abolished.”
The Choate News Editor in Chief Lauren Kee ’24, who is considering whether to pursue media and journalism in the future, says “Mr. Smith was in my role as Editor-in-Chief of The News 70 years ago, and being in the same room together was so surreal. I particularly enjoyed hearing about his experience with the newspaper ... I appreciated that he took the time to hear about our personal thoughts regarding our work on The News His thoughtful insights on the current state of the media in the face of technological advancements and political polarization were intriguing and valuable.”
History has lessons to teach us and guide us, according to Smith. His new book looks back over six decades: “How did we get where we are? It’s an effort to get Americans to focus on history, to understand the roots of our current problems. We think what is happening right now is the most important thing, and we say, ‘How will we get through this?’ History gives you insights, it gives you a footing, it gives you values. In a lot of ways, it gives you hope. If you think about what Lincoln went through, or our nation during World War II — we have examples from history to give us hope.”
Secondly, Smith is conveying the historical lessons of culture. “The Russia I covered in the 1970s and today, if I did my job well, should mean Putin is no surprise. Same thing in the Middle East. This is not a memoir about me. It is about what I saw. And it is important to see what went wrong, what went right. We can’t hide from history, but we can learn from it.”
On issues of economic and political reform, Smith suggests that people of retirement age can work well with young people by sharing their experiences with reform and civic engagement. “Hope requires engagement. We who are retired and the younger generation, aged 20–35 and younger — our generations are more hopeful in general, and can be more engaged in working on issues.”
CELEBRATING THE LEGACY OF JOHN F. KENNEDY ’35 AT CHOATE
Director of the John F. Kennedy ’35 Program of Government and Public Service Ned Gallagher contributed these words about JFK’s enduring legacy at Choate, honoring the 60 th anniversary of his death.
“Reflecting on the impact that his own Choate education had on him, John F. Kennedy observed in 1963, ‘It would seem to me that the task for the future ... is to make sure that our private schools prepare young men and women for service to the community and to the nation. The inheritance of wealth creates responsibilities; so does privilege in education.’
Sixty years after his death (November 22, 1963), the most popular signature program at Choate Rosemary Hall is the one that bears President Kennedy’s name: one dedicated to government and public service. Each spring 18 rising fifth formers are selected to engage in a course of study centered on the disciplines of philosophy, politics, and economics.
Smith says learning, really learning history — the systemic issues raised by concrete events — may inform and guide us in the present moment to make our country and politics better. Choate students seemed to take the lesson, much as Smith took a lesson decades ago from his mentor, Burge Ayres.
In addition to their classes, these students participate in a meaningful off-campus experience related to public service, and — as the culmination of their work in the program — deliver a TEDTalk-style presentation about a public policy solution to some national or global issue in need of greater attention. As part of their onboarding, the newly selected students also read a biography of JFK the summer following their fourth form year, in the hopes of connecting their own journey through the program with the life and work of the School’s most famous alumnus.”
Cybersecurity Rockstar Window Snyder Inspires Students
by susanne Davis
While still enrolled in undergraduate studies at Boston College, Mwende Window Snyder ’93 launched her career as an ethical hacker. As one of the few women in this new field, Snyder took the handle “Rosie the Riveter.” Since then, she has helped to shape the systems that we all use today, including Microsoft Windows, macOS, iOS, and Firefox, to solve a core problem: how to keep our data safe. She has been called a visionary in the field of cybersecurity, blazing trails for corporations like Microsoft, Apple, Mozilla, Fastly, and others to make positive security improvements.
When Snyder, who was on the School’s Board of Trustees from 2007 to 2013, returned to Choate last spring to accept the 2023 Alumni Award at School Meeting, Head of School Alex D. Curtis called her “an online security rockstar.” The renowned cybersecurity expert captured the attention of the student body when she told them that despite all her achievements, in fact, she had struggled academically her first year at school. “I learned that being smart is not enough,” Snyder said. “Being smart and working hard is the killer combination. I never worked so hard for anything in my life. And after leaving Choate, nothing was ever hard again. Not because I didn’t do hard things, but because I knew how to get hard things done.”
As we see the world changing with rapidly developing technology and use of artificial intelligence, this second installment of our series on teaching excellence at Choate — seen through Snyder’s visit — is an opportunity to see how our students embrace that evolving world, while exhibiting the central qualities of a Choate education.
CULTIVATING A SUPERPOWER
As a student at Choate, Snyder excelled in poetry, Spanish, and theater. She had the lead role in A Chorus Line, and for her many contributions in the performing arts, was awarded the very first Legacy Robe. She thought she might become a writer. (In fact, she did, and has co-authored a book with fellow Microsoft application security specialist Frank Swiderski, entitled Threat Modeling.) While she did not study computer science as a high school student, she credits her theater experience for giving her the communication skills she has needed in her work as a cybersecurity expert. “Learning to get up on stage, make a mistake, and keep going, to experience failure — to have that experience? That is a superpower I learned at Choate.”
SUPERPOWER EMPLOYED
Snyder attributes her determination and love for technology to her mother, who left her teaching career to become a software engineer when Snyder was a child. Her mom taught her to program BASIC, an early programming language, on a Texas Instruments PC when she was just five years old. It was as an undergraduate that she turned her creativity and willingness to explore — central tenets of a Choate education — to studying computer science and mathematics at Boston College, where she was developing tools and working on security research before she even met others in the Boston hacker community.
Snyder was a software engineer on security critical systems and developing security products before she went to the computer security firm ATstake. She moved to Microsoft as a senior security strategist, and says her major contribution at Microsoft was owning security sign-off for the Windows operating system. “I was the first in this role, and it meant that every security bug and feature went through me for multiple major and minor releases of the OS.” There, she also pioneered the Blue Hat Microsoft Hacker Conference, bringing Microsoft developers together with hackers to detect and fix vulnerabilities within the software.
Snyder’s experience at Choate on the stage and expressing herself effectively in a variety of media honed communication skills that helped early in her career to convince Microsoft to include security as part of the software development cycle, rather than a feature added on afterward. She contributed significantly to developing the first versions of the Windows operating systems that implemented those developments, led Mozilla’s security team, managed Apple’s privacy and security teams, and built the security team at Fastly. She was also chief security officer at Square. Many of the roles she held did not exist before she created them.
Then came a moment, as had happened at other times in her career, where she saw another security gap, in something called the Internet of Things (IoT) — those devices that connect to the internet and have varying levels of security: cars, washing machines, refrigerators, coffee pots, cell phones, as well as devices that manage civic systems such as aviation control, municipal water management, and medical facilities. What those devices have in common is that they house a fully functional computer within — often without adequate data protection security. In 2021, Snyder launched her startup, Thistle Technologies, and set to work trying to address vulnerability, with the intention of creating discrete security capabilities that developers could incorporate into all kinds of devices to increase security resilience.
SHOWING STUDENTS THE DIGITAL FRONTIER
On the day Snyder returned to campus to accept the Alumni Award, she attended Matt Bardoe’s Autonomous Robotics class. The course is part of the Advanced Robotics Concentration (ARC). “I often felt then and thought during my visit, wow, these are classes I’d like to take,” Snyder says. “I felt a little bit of envy that I’d like to go back to school and take Autonomous Robotics. I took Robotics as an advanced elective in college, where only a small group of students got into the class. You couldn’t take it until far along in the program, and it filled up quickly.”
Bardoe says there was a great back and forth conversation between Snyder and the students: “She was one of the best alumni visitors I’ve ever had in a class. She connected with the students as a fellow Choatie and inspired them to take the lessons learned here to make a positive impact in the world.”
The students demonstrated to Snyder the robots they built, and Bardoe says,
“Even
though Window uses different kinds of technology than the robotics students were doing in the course, there was a general understanding of the field. Window talked about her work protecting computers from hacking, and what it is like to face the challenge of being a diverse student in the field.”
Favour Olagunju ’25 says Snyder’s words and experience with computer security helped her figure out what type of engineering she wanted to pursue. “As a black female in STEM, there have been times throughout my life when programming and STEM seemed intimidating because there weren’t many females with the same passions as me,” Olagunju says. “However, Ms. Snyder serves as an inspiration, and demonstrates that women like me can succeed in STEM fields. She gave me hope.” After Synder told the class about the threat modeling she developed for Microsoft, Olagunju says she now wants to be involved in cybersecurity, “protecting information from malicious attacks.”
Eric Yang ’25, a second-year student in the ARC program, took Design and Fabrication and Competition Robotics courses before Autonomous Robotics. He was interested to hear Snyder talk about the security in the students’ robots:
“In the real world, we must design systems that are not only practical, but secure. Ms. Snyder is a major part of the industry. She shared experiences we cannot otherwise get. Her saying that she learned to do hard things at Choate was a strong takeaway for me. That’s the mind set we acquire here.”
“The students were a little in awe of Window,” says Travis Feldman. Snyder visited Feldman’s Machine Learning class. “She was very personable, down to earth, and there was a real spark of curiosity that the students displayed when she gave them narratives of what it is like out there on this digital frontier. They are interested in being on the edges of any known career path, not so much to follow her directly, but enthusiastic about her example.”
Feldman says Snyder gave a clear instance of real-world perspective. “These kinds of visits give points of traction,” he says. “This helps students move the class work and the tutorial exercises to application beyond the classroom.”
Learning that is directed outward toward the world is a major focus of Choate’s Lin i.d.Lab, which Feldman directs. He is an English teacher and says the lab’s multidisciplinary approach draws classes from across campus, where students explore their passions, not mere assignments.
Work in the i.d.Lab encourages creativity and resilience. “Students experience for themselves that it is okay to fail and experience the benefits of acknowledging that, working with what appears and might be a failure in front of you. It’s a perfect opportunity for us to cultivate one of the central qualities of a Choate education: to balance perseverance and resilience with humor and joy.”
While the i.d.Lab did not exist during Snyder’s time at Choate, it fosters a culture of taking risks, learning from failed attempts, and building resilience much like what Snyder described on the Choate stage and in her Choate academics. Feldman says, “The i.d.Lab serves as a catalyst for our curriculum. It takes students beyond the traditional STEM subjects, science, technology, engineering, and math, and incorporates the art of elegant design.”
AN ELEGANT DESIGN
Snyder illustrated the concept of elegant design when asked just how visionary thinking is developed.
CENTRAL QUALITIES OF A CHOATE EDUCATION
Alumna Window Snyder displays characteristics of a life-long learner and the central qualities of a Choate education. She graduated two decades before a 2014 committee articulated in a formal document those core qualities, including perseverance and resilience balanced with hu-mor and joy, self-advocacy balanced with commitment to serve others, cultivating creativity and a willingness to explore. But the result of the committee’s work made explicit the Choate student experience that alumni surely recognize.
“ There are three things,” Snyder says. “First, you must assess where you are. Next, assess where you want to be, and third, ask the question, what are the gaps between the two that need to be addressed?”
Snyder’s advice may apply to most anything in life. The quickness of her mind gives a glimpse of her intense curiosity and commitment to excellence. Her Choate visit serves as both an example and inspiration to students who are also eager to be a positive force in the world.
The Central Qualities of a Choate Education align with the School’s Mission, Statement on Character, and Statement of Expectations and was joined by the Institutional Statement on Diversity, Equity and Inclusion and our commitment to sustainability to create a collection of documents that reflect our values and priorities in the student experience. It reads, and remains true today:
“Dynamic balance characterizes the Choate Rosemary Hall experience. It is at the core of what we value and teach, both in and out of the classroom, preparing our students especially well for success in a world filled with challenges and opportunities. Those who seek to contribute in the global community must balance a wide range of interests and perspectives. Doing so requires understanding and adaptability along with a commitment to action, a desire to be a positive force in the world.”
The School’s values regarding the student learning experience have been constant, even as we practice a dynamic balance and embrace new frontiers. Amid evolutionary cultural changes, we celebrate the enduring compass the School’s core values and the Central Qualities of a Choate Education provide.
Read more about the Central Qualities of a Choate Education:
The Power of Representation
by sus Anne dAvis
Photo
This academic year, the Bulletin has offered a series looking at how teaching happens here at Choate Rosemary Hall, peering through the lens and stories of inspiring alumni who made recent visits back to campus. In the fall ’23 story, two-time Pulitzer Prize winner Hedrick Smith ’51 implored students to really learn history to inform and guide our present moment to make our country and politics better in the future. Cybersecurity Rockstar Window Snyder ’93 balanced a present, real-world perspective of the digital landscape with the kind of visionary thinking that has always been at the core of a Choate education in the winter ’24 issue. In this third and final feature, we offer a story highlighting tech entrepreneur Natalie J. Egan ’96, whose visits to campus illustrate that teaching excellence extends beyond the classroom and includes our support for the whole person as part of the educational journey.
NATALIE J. EGAN
TECH ENTREPRENEUR
Recently, Choate alum Egan shared a simple message to a packed room of students, faculty, and staff on campus: “We can’t understand each other until we understand ourselves.”
Photo credit: Joey Avena
Egan presenting “Cultivating Connection & Belonging” on Diversity Day
For Egan, a serial technology entrepreneur and CEO of a training software company called Translator, Inc., that understanding took many years. She remembers a time when she was five years old walking into her mother’s closet, trying on some of her clothes, looking into the mirror and feeling pretty for the first time. When her mother walked in, Egan remembers, “I thought, ‘I can never do this again, I’m supposed to be a boy!’ But more than that, I was supposed to be a bro!”
“To my big brothers,” says Egan, “I was Lil’ Bro; to my younger sister, I was one of three ‘Big Bros.’ And of course, I didn’t want to let anyone down,” says Egan. That was part of her family legacy, as was Choate. Her grandfather, William C. Egan C 1932, was an alum, along with her father, Raymond ’62, brother Stouffer ’87, and sister Erin (Egan) Eastland ’97.
“ The message and the pressure were implicit: don’t mess this up. I wanted to be a successful business‘man’ like my brothers and my father and my grandfather, but it never felt right.”
Natalie, age 4, center
Natalie at Choate
Natalie with her children
Photo credit: Trillium (Sellers) Rose ’96
Photo credit: Fran Spangler
Photo credit: Lynn Lynn
COINCIDENCE LEADS TO CONNECTION
Director of Alumni Relations Andrea Solomon recounts the story of Egan’s calling in 2016 in advance of Reunion Weekend so “we could have her name tag right.” Coincidentally, fellow alum Alison FitzSimmons ’91, who had also recently transitioned, was coming back too. The two women had not known each other beforehand. “That’s when we started to think that this might be a cool opportunity to do a program, if they were willing,” Solomon says. The program was originally scheduled to be held in the Science Center lounge, but so many people showed up that the program was moved to Getz Auditorium and still overflowed, with about 150 guests.
Then-Director of Student Activities Jim Yanelli moderated the panel as the two trans women talked about their adventures through time and across genders, sharing honest stories about the joys and challenges of their lives in various roles, including child, student, spouse, parent, and employee, coworker, or colleague. Solomon says it was one of the most moving alumni programs to that point.
Egan says after that, she looked up to FitzSimmons as a big sister and a mentor. When FitzSimmons, a lawyer, passed away suddenly, it was a wakeup call for Egan.
“There are so few of us ‘out’ as transgender alums. How can I help destigmatize the trans identity and create representation for current and former Choate students, so they don’t feel they are alone?”
FOR THE CULTURE
As one of this year’s Diversity Day workshops, Egan shared her story, accompanied by photos, through her different “Bro” phases to cultivate the kind of connection and belonging she has been working for since her transition. She named her first phase the “Lil’ Bro” phase, followed by the “Lego Bro” phase. “I built worlds I could be in,” she says. “I imagined myself the Princess in the castle, but no one knew that.” Egan says her “Choate Bro” phase formed “some of my best friendships. Even though I couldn’t be myself, Choate helped me start to see the world differently beyond what I thought was possible, especially for the time.” Her “Frat Bro” phase at Cornell marked her employing toxic masculinity. “This was where I learned weaponization of humor, and I used drugs and alcohol to get away from myself.” Egan’s “Dad Bro” phase she calls “one of the most amazing experiences of my life, and also one of the most confusing because I truly wanted to be a mom.” Today, she has three children: Van, age 18; Brook, age 16; and Teddy, age 11. In her “CEO Bro” phase, she started her first software company, PeopleLinx, and raised $7 million in venture capital. Egan says being a CEO was also part of her family legacy (her father and brothers were business owners or CEOs). She felt she was born to “be a CEO, like it was a rite of passage or something I was supposed to do.”
Photo credit: James Emmerman
Natalie featured in Elle Magazine
“But, in 2016 everything crumbled, including my marriage,” Egan explains. “I came out as a transgender woman, and my business fell apart. Suddenly, at age 39, I faced bias, discrimination, and hatred for the first time. As a white cis male, no one had questioned me. I didn’t know what privilege was until it was taken away from me.” The journey to empathy started then, with her coming to terms with who she really was.
Dean of Equity and Inclusion Rachel Myers said she knew Egan’s Diversity Day presentation would be powerful and well received.
“Natalie is a living representation about how one’s mindset and experiences around culture and diversity is not fixed. We do change and grow over time, and the people and places we encounter impact us in powerful ways. Sure, Natalie is not the same person that she was when she attended Choate — but what is most powerful are the ways in which she reflects on her cultural journey during Choate and afterward: how she experiences a cultural shift and how others treat her because of it. And she has used her incredible talent and intellect to create a software product to help organizations be better at creating inclusive, positive workplace culture among diverse employees.”
— Rachel Myers
To illustrate the power of the Translator software, Egan guided students, faculty, and staff through a real training workshop using the technology platform. During the session, the software provided an automated curriculum focused on Diversity, Equity, and Inclusion while participants anonymously entered stereotypes and labels they had experienced into the app. Egan showed some of those words on a screen, making the point that often these words revealed stereotypes, full of critical judgment. She then asked participants to enter into the software program words they felt identified their authentic selves, words that were much more positive. “Where are we cultivating community, and connections?” Egan asked the audience. “And where are we stereotyping, gaslighting, and/or disregarding?”
When one student asked, “how do we cultivate connection?” Egan responded, “Empathy and humility. These qualities are displayed through curiosity, not judgment.”
Photo credit: Michael Branscom
CONNECTING WITH STUDENTS
In 2023, Egan visited Kyra Jenney’s Queer Studies and Gender Studies classes. “Profound gratefulness exists at Choate for Natalie,” says Jenney, History, Philosophy, Religion, and Sciences Department head. “Her continued involvement at Choate, even as she’s in a high-pressure business environment, and what she has done with Translator shows her genuine interest in sharing for the benefit of others. She has a strong affinity for and love for this place. It is so helpful for our students to see people successful in business as entrepreneurs, and also to see her as a full person,” Jenney says. “For multiple trans and nonbinary students, Natalie’s visit to our classroom was their first time seeing an out trans person visiting Choate.”
Mikayla DaSilva ’24 said Egan’s visit to Queer Studies showed “real-life aspects of what our class covered from queer praxis to just living her life as a queer person and what that means to her. In a class environment, you’re studying from a third-person perspective. Sure, you can use primary sources, but to speak to someone who went to Choate and therefore had similar formative experiences to you and to learn about their life puts the theories into a relatable context. That way we’re not just studying ideas, but the implementation of ideas into the daily lives of queer people in our community.”
During her campus visit in 2023, Egan also spent time with the Counseling Center staff, and Director Raynetta Gibbs said, “Embracing one’s true self is a journey of courage and resilience. Natalie visited us in the counseling office to share her story and insights on navigating the complexities of identity during those formative years. We were happy to hear her ideas about facilitating programming that fosters understanding and acceptance for students who struggle with identity in independent boarding schools and will continue to have open dialogue on ways to help students in our community.”
DEVELOPING AN INCLUSIVE ENVIRONMENT
Jenney says that when she arrived at Choate in 2012, there was a gender studies course called Women’s Studies that offered a global focus. As increased interest began to develop, the courses got revamped with a focus on gender studies and gender theory. As more trans and gender-nonconforming students enrolled, the School responded not only with courses, but also with schoolwide programming, affinity groups, and all-gender housing options.
“With the increased rate of suicide ideation among teens, let alone among LGBTQ+ students, we need to support representation in this area,” says Jenney. “We have an opportunity to address some of our societal problems by creating more representation and more empathy.”
When asked what it meant to her to see the changes at Choate since her time as a student, Egan says,
“ The world has changed. If I were a student at Choate today, one of the things I would see is more representation. The power of representation is everything. Sometimes we can move the needle just a little, so someone, somewhere, somehow, might feel so not alone.”
ALUMNI VISITS TO THE CLASSROOM
Kristen Andonie ’17 visited — as part of the i.d.Lab Alumni Series — and hosted a robotics and software engineering workshop focused on the scrum design process.
Dipti Bramhandkar ’96, a guest artist for two days, visited Postcolonial Literature, Acting II, Screenwriting/Playwriting, Improvisation, and Acting III, Honors. She also performed her monologue American Rookie in the William T. Little ’49 and Frances A. Little Theater.
Natalie Egan ’96 offered a Diversity Day workshop “Alumni for the Culture,” demonstrating Translator training platform.
David Mills ’84 visited a Reading and Writing Poetry class and gave a poetry reading from his book Bone Yarn
Wake Smith ’75 met with KEC students to discuss his book on climate change, Pandora’s Toolbox: The Hopes and Hazards of Climate Intervention
Tom Viertel ’59, P ’89 spoke to the student body during School Meeting after receiving the Distinguished Alumni Award. While on campus, he visited Acting II class, met with Arts Concentration students, and watched the rehearsal for the spring musical Into the Woods
From the most formal, to the more casual, we appreciate the time and experience alumni share with our students each year. They enhance the classroom experience for every student and connect students to the lives of leaders in the service of others.