Oprah Winfrey and Lucy Kaylin ’81

Enriching the Conversation

by Andrew Wickenden ’09

As a young writer at GQ, Lucy Kaylin ’81, now editor-in-chief of O, The Oprah Magazine, learned that “it’s not enough to describe things well and report things evenly. If you’re going to write for or edit an interesting magazine, a magazine that means something, you have to have a point of view.”

At O, that point of view derives from the magazine’s tagline, mantra and ongoing encouragement to the reader: “Live your best life.”

“That’s the core idea, and something Oprah really believes in and exhorts everyone to pursue, whatever that means to you,” says Kaylin, who has worked at the magazine since 2009, first as deputy editor before rising to her current role in 2013. “We’re a magazine that wants women to take more from life and not be complacent, to look deeper inside themselves and their experience and find ways to make it richer.”

While each issue tackles a specific theme from various angles in various forms, with content in print and online, the magazine tends to “gravitate toward personal narratives,” Kaylin says, “because we want to have a conversation with our readers. We don’t want to preach — we want to talk with them. And we want them coming away with a sense of support, that we’re friends on their journey.”

In the February 2016 issue, which focuses on mental health, the media mogul, philanthropist and magazine’s namesake, Oprah Winfrey, opens up about her “face-to-face” experience with mental illness, recounting that “several people close to me were hospitalized with severe suicidal depression and manic and schizophrenic thoughts.”

“Mental health is an issue affecting a vast number of American women, but it’s something that still has a lot of stigma around it and women aren’t sure about how to get the help they need,” Kaylin says. “With this issue we wanted to change that.”

By engaging with readers on an intimate level, she explains, “our interaction is alive, and readers’ connection to the magazine is not casual. I’ve been lucky to work at great magazines, but one thing I felt was unique at O was this vital and real conversation going on between us and the reader. There’s this really fleshand- blood sense of who the reader is and that we’re writing and speaking directly to her — that sense that she’s right there when I’m thinking about what to put in the magazine.”

Kaylin got her start in the magazine industry as a fact-checker at Vogue. She then spent nearly two decades working at the men’s magazine GQ, contributing more than 100 articles and dozens of cover profiles, including the controversial, widely quoted interview with Tom Cruise in 2006. Kaylin rose to features editor at GQ before becoming executive editor at Marie Claire, where she wrote cover stories, interviewed President Barack Obama and was instrumental in the development and execution of Marie Claire’s reality show on the Style network, Running in Heels, in which she appeared. Since Kaylin became editor-in-chief of O, the title has won two National Magazine Awards, the industry’s Oscars.

Kaylin is the author of two books, For the Love of God, about the decline of Catholic nuns in America, and The Perfect Stranger, about the complicated relationship between mothers and nannies. She also contributed an essay to the anthology The Secret Currency of Love, about the role money plays in relationships.

During her time at William Smith, Kaylin was a member of Hai Timiai, the senior honor society, and received the White Essay Prize. She graduated cum laude with highest honors in English and went on to receive a master’s degree in English Literature from Columbia.


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