Gail Sheehy Leads Daring Life

Originally published Nov. 4, 2014

She has sat with world leaders, absorbing their ins and outs—both Presidents Bush and Bill Clinton, British Prime Minister Margaret Thatcher, and Egyptian President Anwar Sadat, to name a few—before penning books and articles for the masses to read.

Her accolades include the Washington Journalism Review Award for Best Magazine Writer in America and the Anisfield-Wolf Book Award, joining the ranks of Langston Hughes and Martin Luther King Jr. Her book “Passages” was named by the Library of Congress as “one of the 10 most influential books of our times.”

Her name is revered in the biography world and journalism sphere, with a career that has spanned decades and transcended fame, power and inherent danger. She is a lesson in feminism, with a story of her own that has empowered women around the world.

But when Gail Sheehy arrived at Page at 63 Main on Sunday for brunch, she was simply a local returning to a staple eatery in downtown Sag Harbor after taking a yoga class around the corner.

The 76-year-old blew in with a strong wind, wearing a tangerine parka and matching sweatshirt, black yoga pants, and sparkling blue sneakers. The energy she brought to the brunch table could be felt across the room—familiar to a reporter, because she spoke and listened with the same eagerness of an interviewer sitting across the table.

When it comes to other people, Ms. Sheehy has studied them closely. She has traveled overseas to understand the struggles of wartorn areas. From assignments for New York magazine and Vanity Fair, to her work as a biographer, she has witnessed the struggles of both political heavyweights and everyday Americans—spending a year in New Jersey after the September 11 attacks, interviewing the families of those who never made it out of the Twin Towers, for her book “Middletown, America.”

But to write her latest work, a memoir titled “Daring: My Passages,” Ms. Sheehy studied herself. She went back to friends and family members, recalling her triumphs and pitfalls as a female journalist breaking the glass ceiling—or, more accurately, sneaking down the back steps of the New York Herald Building to pitch a story to the esteemed editor and creator of New York magazine, Clay Felker, her future husband.

“Life,” she said, “is about these daring moments. And that one was the most daring moves I’ve ever made.”

That moment, she said, led to a successful career working under Mr. Felker at New York magazine, the couple’s longtime home in East Hampton for 30 years—she now rents a house in Sag Harbor—and a passionate relationship that would last until his death in 2008.

“We shared what I called ‘creative intimacy’ before it was romantic,” she said, taking a sip of her English breakfast tea and honey.

When she spoke of her late husband, it was as if he were still alive, waiting for his wife to come home from brunch. When she spoke of his later years—specifically, the decade-plus he spent battling throat cancer, as she took on the role of his caregiver—her eyes sparkled, as though each day was nothing less than a dream, as though her life, though trying, was a fairy tale, dictated by what was right for her in the moment.

Throughout her career, Ms. Sheehy broke down barriers both in the home and the workplace that unlocked a blend between being a family-oriented woman while also successful in her chosen career—which is where she differs from modern-day voices, such as Arianna Huffington and Sheryl Sandberg, she explained. Ms. Huffington and Ms. Sandberg have written recently on women’s roles in the workforce and in the family, both making a case for equal priorities in work and family life.

“I don’t subscribe to having it all,” Ms. Sheehy said. “I think that’s a false promise that’s only going to lead to disappointment for most women. What matters is having what matters, and what matters changes at different stages in your life.

“In your 20s, you’re finding out who you are … You’re failing,” she continued. “Oh, yes, it’s very important to fail, and that’s the time to do it. You find out that you don’t die from it. Then you learn how to fail upward and learn how to take that failure and use it toward the next step, and how to be daring.”

Daring, for Ms. Sheehy, is the best way to overcome trepidation—the motive behind writing her narrative.

“When I fear,” she said, “I dare.”

The title of her memoir is a nod to her most famous work, “Passages,” published in 1976 after three years of research and 115 in-depth interviews about personality changes common to each stage of life, the developmental rhythms of men and women—which she found, perhaps not surprisingly, to be remarkably unsynchronized—and how to combat inevitable crises.

Since “Passages,” the author has penned 16 books and profiled a handful of the world’s most powerful leaders—including both President Clinton and his wife, former Secretary of State Hillary Clinton. Digging into her own history and exposing herself was an entirely foreign challenge, she said, likening it to “pulling apart your ribs and digging under there. God knows what you’re going to find.”

What she found, however, was worth the prod.

The memoir, which Ms. Sheehy plans to discuss next month during a League of Women Voters of the Hamptons-sponsored reading, takes readers through Ms. Sheehy’s journey as a pioneer for all women searching for balance in life—for those who wanted to do only what mattered to them in that moment.

“I wrote what I lived,” she said of her memoir, which was published in September by William Morrow, an imprint of HarperCollins. “It wasn’t for any ideological purpose. It was about being honest about what I lived and what I learned.”

For more information about Gail Sheehy and her memoir “Daring: My Passages,” visit