University of Vermont

Vermont Quarterly

A Conversation with Gail Sheehy ’58

Gail Sheehy
Gail Sheehy ’58, photograph by Gasper Tringale


A Conversation
with Gail Sheehy ’58

by Thomas Weaver

Among the pioneers of “new journalism,” Gail Sheehy has written profiles and biographies of figures such as Margaret Thatcher, Mikhail Gorbachev, and Hillary Clinton. Her 1976 book, Passages: Predictable Crises of Adult Life, was named one of the ten most influential books of our time by the Library of Congress. Going strong at age seventy-seven, Sheehy published her seventeenth book this fall, Daring: My Passages, a memoir.

So much for Gail Sheehy’s father doubting the viability of his daughter’s career aspirations as a writer, insisting that she combine her English major with studies in home economics. On a December morning, Vermont Quarterly editor Thomas Weaver talked with Sheehy about her career, UVM days, and the focus of her recent work.   

Vermont Quarterly: Looking through back issues of the university magazine, I noticed you returned to UVM and gave a talk at your twenty-fifth reunion in 1983. A questionnaire back then asked alumni to name what they saw as the three most important qualities for a person to have. Care to guess what you wrote?

Gail Sheehy: Oh, my gosh. You mean what I saw as the most important personal qualities for an individual to have at that point in their lives, right? I would say honesty, persistence, and lovingness.

VQ: You said, “Imaginative, playful, and ambitious.”

GS: Well, it's interesting, those are kind of younger qualities. They're more related to people under fifty. In that Reunion how old would we have been? Getting close to fifty. Fifty is when people take off and are often happier than at any other time in their lives.

We start out happy in our early twenties. Then with parenthood and raising children, there's a slump in the thirties into the forties. Then it starts picking up, and by fifty people begin to feel more themselves, more certain of where they're going, and then more playful and imaginative.

I said “honesty” when you asked me now because I think once you move into the “selective sixties,” as I call them because you have to select what's really important to you because you don't have all the time in the world left, being honest with yourself is essential. Taking an inventory of your life, what you've accomplished and what's missing.  So being honest with yourself —changing what you can and accepting what you can't—is a very important part of this afternoon of life. You can't afford to have a “false-self” anymore. This is it. This is, you know, the sub-totaling time.

VQ: Imagine we brought you up to UVM, and you spent the night in a residence hall room with three roommates. You talk late into the night. What would you want to tell this generation of young women?

GS: I’d want to tell them to dare. That’s what I found, when I came to the end of my memoir, has been the theme of my own life. I think it is very important to encourage young women, in particular, to be daring. Take chances. Travel to some really far off or unfamiliar place when you’re in your college years to find out how you survive. Expose yourself to other parts of the world; look back at your own country and see its strengths and its flaws.

Try a difficult sport that you’re not good at. Maybe you find out you have strengths you didn’t know. Try subjects that are not your strong suit. Everybody has to become better at tech—so take math, take computer science.

VQ: You seem to be reaching out to a younger generation of women with your web/social-media driven Daring Project. (, #DoYouDare.)

GS: It’s been exciting that I’m getting these stories from women of all ages who are doing terrific, daring things. I would love to invite women students at UVM and alumnae to send in their daring stories. I pick out the interesting stories, call them, interview them, and post them.

I’m also writing about the early daring moment of famous women, who almost routinely failed and sometimes failed a lot of times before they really took off. Some had to fight crippling shyness or fear. Gloria Steinem told me she was scared shitless the whole time she was doing Ms. magazine. It is helpful for young people to know that people who have done very, very well have really had to fight a lot of the same kinds of things that hold back young women today.

VQ: The section of Daring on your UVM years tells quite a story of an almost-elopement with your boyfriend.

GS: The good part of that really, really, really foolish act was that it gave me such a deep appreciation for the education I almost missed. I became a grind and really valued my studies. But I was also in a sorority, Alpha Chi Omega, and we learned how to throw parties.

VQ: You’re in a rare place as a writer with a high degree of celebrity. How do you balance the solitary work of writing with the more public aspects of your life?

GS: Once you learn how to do the public part, which takes a long time, it’s a wonderful balance, actually. It is solitary and lonely to work just you and your legal pad, your computer, and books. Especially doing a memoir where I was only researching myself and my times. You get to really be sick of yourself.

The way I learned to enjoy the book tour most authors hate, and I hated at the beginning, is when I realized, “Hey, this is like taking a show on the road.” You have to learn to be an actor. You have to get your wardrobe, get your makeup, get your lines, and go out and do a show. Then it is so totally different. As you get better at it, it becomes fun. You get a lot of feedback, and you learn a lot.

VQ: Did you really coin the term “aha moment”?

GS: I think so.

VQ: That’s really something. You could have “Aha” on your tombstone one day.

GS: (Laughs.) I like that idea.

VQ: Good. I wasn’t sure I could make that joke with you.

GS: After all, it’s what the aha moment took me to.

VQ: Tell me a bit about your writing process as you worked on this latest book.

GS: Morning is always best for me and I think for a lot of writers. And as I get closer and closer to a deadline, I get up earlier and earlier. So I would try to go to yoga at 6:30 a.m., get back, do a little treadmill to read the paper, then come back and get in front of the computer by 8 and really work until 1 o’clock. Then I take a brisk walk to go get lunch and shake things out. Come back and write in the afternoon. Nap at 4 o’clock. If I don’t nap at 4 o’clock, I’m actually napping at my computer and not getting much done. After that nap, it’s like I have another workday in me.

VQ: No kidding, so after that nap you go back to work again?

GS: I work until 6 on dealing with emails and various chores. Then I’ll watch the news. If I’m in the thick of a project I’ll do some research in the evening or send out emails to set up interviews… or I might go out and have some fun.

VQ: What was it like working on this memoir, focusing on your self instead of writing as a journalist?

GS: Much, much harder. That was the great struggle. The other muscle is very strong and confident. To actually delve into your own motives and thoughts and fears and try to be honest with yourself, it’s like pulling apart your ribs and doing an excavation underneath there. You find some jewels, and you find some bitter stones, and you find some expanses that are almost inexplicable. You know, “Why did I take so long to get remarried?” It would take me sometimes several months to ponder a period of my life and try to put together what was happening and why I behaved as I did.

It was very, very cleansing. I think anybody in their sixties or seventies if they wrote a memoir would find it a satisfying exercise in doing what we have to do at that age, which is come to terms with our lives and give a blessing to the life that we’ve lived. 

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