What does it mean to be transgender? What is gender identity? This year’s Talbot Speaker, Professor Jennifer Finney Boylan, answered these questions for students and faculty, with charm, personal anecdotes, and compassionate advice. Professor Boylan is the inaugural Anna Quindlen Writer-in-Residence at Barnard College and the author of She’s Not There: A Life in Two Genders.

“The question is not how you go from being a man to a woman, or a woman to a man,” she said. “The real question is: How do you live an authentic life? How do you be you, out in the world? That well-intentioned advice, ‘Just be yourself,’ can be the most difficult advice to follow.”

Milton’s 48th War Memorial speaker, Professor Randall L. Kennedy, told students, alumni and parents that despite “a chasm that separates the circumstances in which whites and blacks typically find themselves” he is still an optimist about race relations in the United States. Mr. Kennedy is the Michael R. Klein Professor at Harvard Law School, where he teaches in the fields of criminal law, contracts, and the regulation of race relations. On Tuesday evening in the Fitzgibbons Convocation Center, Professor Kennedy continued an important Milton tradition that brings to campus public figures who discuss core social and political issues.

Although the election of President Barack Obama was an amazing and pinnacle moment for America, Mr. Kennedy said many African-Americans were deeply affected by the economic downturn and believe President Obama has “been too fearful of being charged with racial favoritism and has done too little to educate the public on the hazards that blacks face.”

Milton’s facilities department recently took great care in restoring one of campus’s most beloved buildings. Straus Library—one of the School’s original, Georgian structures—housed the Milton Academy library from 1929 to 1971; it now serves the college counseling office and is a gathering space for formal and informal events. This summer, a devoted maintenance team, led by Associate Director of Facilities Steve Zannino, corrected structural damage and completely restored Straus’s back patio.

A formal, traditional expression of School life, Convocation marks the start of the academic year: new opportunities, new faculty, and new classmates. Messages from Head of School Todd Bland, Upper School Principal David Ball, and Milton’s co-head monitors, Caroline Wall (I) and Louis Demetroulakos (I), were highlights of the ceremony. Mr. Bland urged students and faculty to approach this year with a positive, “glass half full” attitude. He drew on the example set by Lou Gehrig, whose grace and positivity in the face of his career-ending diagnosis can be an inspiration to all of us. Mr. Ball’s message, which began with a personal (and hilarious) childhood tale of horseback riding in the “grand, majestic American west,” encouraged us to practice “urgent optimism” and “infectious action”—to “stand up, stand for, and give to.” He spoke of the Wright Brothers, who as young boys believed they could transform the human experience through flight, which they did without funding or formal education. “Pedigree doesn’t determine the success of innovation,” Mr. Ball said. “Passion does.”

Walking the bustling, friendly streets of Rabat is a happy memory for Shaheen Bharwani (I), who plunged into the Arabic language and customs of Morocco this summer.

“Interacting with strangers in Morocco was easy,” says Shaheen. “They treated me like a friend and made me feel so welcome. The man at the end of my street invited me to tea one day while I was on my way to school. So we sat together before I headed off.”

Shaheen earned his six weeks in Morocco as a result of the National Security Language Initiative for Youth (NSLI-Y) program funded by the U.S. State Department. The program looks to increase the number of Americans learning, speaking, and teaching critical-need foreign languages, like Chinese and Arabic. Shaheen was selected and awarded a scholarship to travel with 15 other students, who lived with host families in Rabat. He spent five days a week in the classroom studying Arabic, including lessons in the local Moroccan dialect and Arabic calligraphy. During free time, students toured famed locations of the region: the Sahara Desert, Ibn Battuta’s tomb in Tangier, the market square of Marrakech, the palaces of Meknes, and the winding souks of Fez.

Artist Anne Neely’s large canvases, with rich hues of blues, greens and browns, hang in an exhibit hall in Boston’s Museum of Science. The paintings in Water Stories: Conversations in Paint and Sound reflect Anne’s interpretation of water issues plaguing the United States. This merging of art and science developed from a collaboration between teacher and former student.

Anne was new to the visual arts faculty in 1974, and David Rabkin ’79 was one of her students, whom Anne describes as “inquisitive and full of ideas.” They kept in touch on and off over the years. David earned his doctorate in technology and innovation management from MIT and is now director for current science and technology at the Museum of Science. Anne retired from Milton in 2012 and focused on her art, specifically the phenomena of water, a subject of her paintings since 2004.