Gail Sheehy
Gail Sheehy interviews Hillary Clinton for Vanity Fair in 1992. Photo courtesy of Harper Collins

[B]est-selling author Gail Sheehy ends her recent memoir with a quote from a friend who convinced the chronicler of everyone else’s “Passages” — her work by that title is one of the modern era’s 10 most influential books, according to a Library of Congress survey — that she should write about her own life.

“You’ve been fearless in exposing yourself to new experiences and challenges — you’ve taken LSD, you’ve jumped out of airplanes, you dressed up in hot pants to walk the streets with hookers, you embedded yourself in the Irish civil war before anybody ever heard of embedded reporters and got caught in crossfire, you even scared presidential candidates — didn’t the first President Bush shudder and say, ‘Is this going to be a full psychiatric layout?’”

For the 78-year-old Sheehy, it all began at the University of Vermont. But the thousands of students and supporters who heard the 1958 alumna speak at Sunday’s commencement in Burlington may have wondered why she talked more about the millennial generation than about her own school memories.

That’s because the world-renowned writer almost didn’t graduate.

Sheehy, in an interview, rewinds to the night a ladder hit the sill of her third-floor dorm window. The 17-year-old New York freshman had arrived on campus just three weeks earlier to double major in English and, to make her father happy, home economics. With the doors of the women’s hall locked for curfew, she watched her boyfriend reach out, rung by rung, with a new plan.

What looked like a scene from “Romeo and Juliet” was anything but romantic. Sheehy was secretly pregnant. Her 22-year-old beau was a Korean War veteran with physical and emotional scars. And the two were unsure of anything other than they would elope.

A last-minute pay phone call to Sheehy’s mother put a stop to that. “Of the procedure,” the author recalls of a subsequent abortion, “I remember nothing.” Sheehy took a bus back to school and stayed put until graduating. Nearly six decades later, she has reason for revealing such a personal story.

“That’s always been my bent — to expose taboos,” she says. “When we share things that are commonplace but shrouded in silence, it helps to relieve the guilt and shame of others.”

Sheehy, as a result, wrote the 1976 best-seller “Passages: Predictable Crises of Adult Life,” which has been reprinted in 28 languages. And 1992’s “The Silent Passage,” inspired by her experience with menopause. And 1998’s “Understanding Men’s Passages,” sparked by her husband’s midlife crisis. And 2010’s “Passages in Caregiving,” spurred by his 17-year battle with cancer.

The author of a dozen other books, Sheehy also has covered presidential candidates from Robert Kennedy to Hillary Clinton and world leaders from Margaret Thatcher to Saddam Hussein for such magazines as New York and Vanity Fair. Most recently, she has written commentary for Politico and The New York Times.

“I didn’t have to write about politics like the boys do, focusing mainly on the horse race and daily polls. I could explore the character of the candidates. That was the epiphany: Issues are today. Character is what was yesterday and will be again tomorrow.”

But even with such a resume, she initially wondered if speaking at her Vermont alma mater might be too much of a challenge.

“I thought, ‘How do I talk to millennials who have such a different world view?’ People in their 20s think they are reinventing the wheel. And, in many more ways than past generations, they are right.”

‘I would dare to be there’

Then again, Sheehy can relate to being a young revolutionary.

Receiving a typewriter for her seventh birthday, the aspiring storyteller was sneaking on Saturday trains from the bedroom town of Mamaroneck, New York, to the bustling streets of Manhattan by seventh grade. The first woman in her family to go to college, Sheehy graduated to a job at the J.C. Penney department store chain’s corporate headquarters, where she was hired by founder James Cash Penney himself.

Sheehy went on to marry a doctor. But seeing the 1963 March on Washington on television, she wanted more.

“I vowed I would not spend my life watching the news on TV,” she recalls in her latest book,

Gail Sheehy
A young Gail Sheehy is pictured on the cover of her memoir, “Daring: My Passages.” Photo courtesy of Harper Collins

“Daring: My Passages.” “I would dare to be there as history happened and write what I saw.”

Her only obstacle: her gender.

“Men wrote about serious issues,” she explains to today’s youth. “Girls in the 1960s wrote about beauty and baking and how to be the perfect engineer of that complex machinery called family life.”

Hired to work in the Women’s Department of the New York Herald Tribune, Sheehy one day walked into the all-male newsroom. She eyed Tom Wolfe, a nattily dressed reporter who would pen such books as “The Right Stuff” and “The Bonfire of the Vanities.” She then spotted Jimmy Breslin, a hard-drinking, chain-smoking commentator who would win a 1986 Pulitzer Prize “for columns which consistently champion ordinary citizens.”

Finally she stopped at the desk of Clay Felker, a man The New York Times would describe as “a visionary editor widely credited with inventing the formula for the modern magazine.”

“What have you got?” she recalls him asking.

While her peers were reporting on charity balls, Sheehy was writing about Harlem women on rent strike, female doctors caring for beaten civil rights workers and uninsured mothers mistreated at public maternity clinics.

Felker pitched her an idea of his own. In 1968, having just launched New York magazine, he asked her to cover Robert Kennedy’s presidential campaign.

“I’m not a political analyst,” she replied.

“The way to make your name as a journalist is not to do lots of little stories,” she recalls him saying. “Tackle a big story, something everybody’s talking about, but they don’t know the why.”

Sheehy sat beside Kennedy on a storm-battered plane when, shivering after a rain-soaked West Coast stop, he asked for his overcoat — which the reporter discovered once belonged to his late brother, President John F. Kennedy. She then skipped a post-California primary party at Los Angeles’ Ambassador Hotel to catch a red-eye flight back to New York.

She arrived home at dawn to a ringing phone.

Bobby Kennedy, her editor said, had been assassinated.

“How soon,” he asked, “can you get me the story?”

‘A lively and healing art’

Sheehy would hear that question often in a half-century writing career.

“Pussycat, how soon can you leave for India?” she recalls Cosmopolitan editor Helen Gurley Brown purring in 1971, assigning a story about Maharishi Mahesh Yogi, spiritual guru to the Beatles, that would land the author in the Himalayas alongside Beach Boys singer Mike Love.

A trip with Felker to the Hamptons led her to discover Big and Little Edie Beale, the reclusive relatives of Jacqueline Bouvier Kennedy and subject of a 1972 New York magazine story, “The Secret of Grey Gardens.”

Sheehy’s own instincts propelled her to war-torn Northern Ireland, only to wind up in the middle of the 1972 “Bloody Sunday” massacre in which British soldiers killed 13 unarmed civil rights protesters.

“High-velocity rifle fire sang into the unarmed crowd,” she would write. “A man grabbed my legs and pulled me down. I lifted my head to see the boy’s face. A bloody socket where one eye should be. What monsters shoot children?”

Sheehy credits her reporting style to anthropologist Margaret Mead, with whom she studied as part of a Columbia University fellowship.

“She gave me brilliant instructions for how to become a cultural interpreter,” says the author, summing up Mead’s advice: “Whenever you hear about a great cultural phenomenon — a revolution, an assassination, a notorious trial, an attack on the country — drop everything and get on a bus or train or plane and go there, stand at the edge of the abyss, and look down. You will see a culture turned inside out and revealed in a raw state.”

In the case of Northern Ireland, however, Sheehy returned home with symptoms of post-traumatic stress disorder at a time when doctors had yet to recognize the condition. Adding to her discombobulation, the writer had divorced — her doctor husband admitted to an affair — and started dating Felker.

Gail Sheehy
Gail Sheehy’s 1976 best-seller “Passages” has been reprinted in 28 languages.

Receiving a $9,375 advance, Sheehy began researching a book about people wrestling with midlife, mortality and meaning.

“Was there some way to demystify professional jargon?” she wrote in its first pages. “To make a lively and healing art of self-examination available to people who, like me, were finding themselves caught in the snarls of growing up adult but, having no guide, were holding themselves or their partners to blame?”

Three years later, Sheehy released “Passages.” The book became a No. 1 New York Times best-seller and remained on the list for three straight years.

Soon she was partying with Jacqueline Kennedy and Harvard economist John Kenneth Galbraith as author Norman Mailer threw a drink in colleague Gore Vidal’s face. And interviewing Egyptian President Anwar Sadat for Esquire and Philippines leader Corazon Aquino for Parade. And writing a New York Times Magazine story on Cambodian refugee children – before deciding to adopt one.

And she was only getting started.

‘Into the world with something to give’

Sheehy would go on to produce “humanized political profiles” for Vanity Fair on figures ranging from self-destructing 1988 Democratic presidential candidate Gary Hart to 2000 Republican contender George W. Bush. The author opened the latter story by asking Bush if he had any reaction to Vermont’s then-new first-in-the-nation civil unions law.

“I missed that,” she quotes him. “Is that like gay marriage? I haven’t heard anything about it. I’d only be interested if it were an issue in Texas.”

In 1992, Sheehy was one of two dozen writers – including Maya Angelou and William Styron – honored at the Literary Lions gala at the New York Public Library.

Gail Sheehy
Gail Sheehy and her husband, Clay Felker, attend the 1992 New York Public Library Literary Lions gala just hours after they learned he had cancer. Photo courtesy of Harper Collins

It was the same day she learned Felker, her new husband, had cancer.

Day after day, Sheehy pureed his food and poured it into a feeding tube, helping him defy medical expectations and prolong his life for at least a decade. But by 2008, covering the last days of Hillary Clinton’s first presidential campaign, she watched his health disintegrate.

“My mind was splintered between the 24-hour cable-news squawk cycle and our own 24-hour life-or-death vigil,” she recalls in her memoir. “I had one week to capture the whys and wherefores in a 10,000-word story for Vanity Fair. I also had to plan a funeral. My powers of concentration deserted me. The fear persisted: Could I still write?”

Felker died July 1, 2008. Sheehy grieved while working on “Passages in Caregiving” and 2014’s “Daring: My Passages.” The 496-page memoir shares everything from her dancing at the University of Vermont with Bill Pickens, grandson of the co-founder of the NAACP and her sole African-American classmate, to her drowning the loneliness of widowhood with wine, leading her to a 12-step program.

“The great heroism of a sober life is getting up in the morning and facing the day, greeting others, going out into the world with something to give,” she went on to write. “When we are in the grave of our own thoughts, feeling like we will never be able to crawl back out, our fingernails packed with dirt, how is it that sometime later we can be laughing, and laughing hard?”

Sheehy continues to work, although not like in the pre-Internet days when paperback rights to one of her books — the titles range from “The Man Who Changed the World: The Lives of Mikhail S. Gorbachev” to the Sept. 11, 2001, inspired “Middletown, America: One Town’s Passage from Trauma to Hope” — once reaped as much as $1 million.

“You can’t really make a living at it today,” she says. “It’s just a very, very difficult thing.”

Sheehy is no fan of social media like Twitter.

“There’s an awful lot of energy that’s not going into adult thinking and writing.”

But the author of the 1999 biography “Hillary’s Choice” can find some good in the current-day candidate generating the most buzz, Vermonter Bernie Sanders.

“Bernie has injected a dose of raw reality into politics and massively broadened the conversation, but he isn’t the first Jewish socialist to win hearts and minds — let’s remember that other radical nonviolent revolutionary who never called the poor ‘lazy,’ never asked a leper for a copay, and was a wild-haired progressive,” says the author, testing out a commencement speech joke about Jesus.

For the rest of her address, Sheehy interviewed students (“I’m thinking about writing about ‘Passages for Millennials’”) so she could speak to their current challenges.

“We used to think that our large brains stuffed with a fine classical education made us unique as humans,” she told nearly 3,000 graduates before quoting French philosopher Rene Descartes’ famous phrase, “I think, therefore I am.”

But that has changed with the advent of computers and smartphones.

“Today, we may better define what sets us apart as humans with a different declaration: ‘I care, therefore I am,’” she said. “Caring may be the key to establishing the unity of mankind.”

With that, Sheehy basked in warm applause. What’s next? The woman who told students that “I could be older than your grandmother” is wondering, too.

“I live life in the interrogative. There is no end to my curiosity. I’m always asking questions.”

Gail Sheehy
Gail Sheehy interviews a University of Vermont student in advance of Sunday’s commencement. Photo by Thomas Weaver/UVM

VTDigger's southern Vermont and features reporter.

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