In this recording of our 30-minute teleclass with best-selling Passages author Gail Sheehy, you’ll hear about women—Sheehy included—who have mastered their fear in order to achieve their potential.
Sheehy, who recently launched the “Daring Project,” encouraging women to be different so they can start dreaming dangerously, talks about what it takes to be daring and the pivotal times in her life when she was afraid to do something but overcame her fear. She’ll inspire you and give you the confidence to leave your comfort zone—and go all out for your dreams.
Listen to the complete 30-minute recording or read the transcript below.
Gail Sheehy is the author of sixteen books, including the classic New York Times best-seller “Passages,” named by the Library of Congress as one of the ten most influential books of our times. As a literary journalist, Sheehy was one of the original contributors to New Yorkmagazine, and has been a contributing editor to Vanity Fair since 1984. She a seven-time recipient of the New York Newswomen’s Club Front Page award for distinguished journalism and won the Washington Journalism Review award for “Best Magazine Writer in America.” A popular lecturer, she was named AARP’s Caregiver Ambassador in 2009.
Conferences for Women
“Women Who Dare”
Guest: Gail Sheehy
Interviewer: Karen Breslau
October 28, 2014
Karen: Welcome to the Conference for Women teleclass Women Who Dare. Our guest today is Gail Sheehy, renowned author of 16 books including the classic New York Times bestselling Passages, which was named by the Library of Congress as one of the ten most influential books of our time. Through her work, Gail Sheehy has changed the way millions of women and men around the world look at the stages of their lives. And as a literary journalist Sheehy was one of the original contributors to New York magazine, and has been a contributing editor to Vanity Fair since 1984. Gail Sheehy’s latest work is Daring: My Passages, a memoir of her life as a trailblazing woman journalist and author. We’re going to be sharing highlights from today’s call on Twitter. You can follow along and join the conversation @Pennwomen, @Texaswomen and @Masswomen. Gail Sheehy, welcome.
Gail: Hi. I’m delighted to be with you.
Karen: Your new memoir is called Daring: My Passages. I’m wondering what the word daring means to you and why you chose that theme?
Gail: Well, when I finished my memoir after three years, I had to sit and ponder, “What was the theme of my life?” We don’t actually spend an awful lot of time sitting around contemplating that. But I was at an age, in my mid-70s, when that was exactly the right thing to contemplate. And I realized it was daring. It was what I do to get beyond my fears. When I fear, I dare. It doesn’t always work. Sometimes I fail. Fortunately I failed early in my career, so I knew I didn’t die from it and I was able to do it again and again. But today failure is kind of the default position for anybody who is daring or willing to take risks, start something new, open their own business, make their own app. You only get there by failing a few times. Failing up, I call it.
Karen: And what is it would you say that holds women back from daring? What keeps them from doing the things you just described?
Gail: I think it’s fear that you’ll be thought to be too impetuous, too aggressive, too unfeminine and mainly that you will fail. That you will embarrass yourself. That you will show that you are not a master of whatever it is you’re attempting to do. And so it’s really important to try to do some things early in your life that you don’t master and realize that “Hey, that’s okay.” But I learned something new and I can do it from time to time, but I’m not going to be the champion surfboarder of the East Coast. And I write about a young woman on my website, where I’m encouraging young woman to share their daring moments. And she was a freshman in college. Her best friend was killed in a terrible automobile accident that wiped out her whole family and the girl wanted to go to Cape Town, South Africa. It had been a lifelong dream.
And so the young woman I wrote about just decided she was going to go to Cape Town for her friend. And she was going to learn how to surf. Well, she never followed surfing. She didn’t know how to surf. She wasn’t even a particularly [sporteous] young woman. But she went to Cape Town. She used her own money. She found a surf shack. They gave her a job. And in exchange for that she got housing and a place to surf and equipment. And she spent six months with girls from all over the country who were doing the same thing. All over the world, I mean. And she never mastered it, but she found out she didn’t die from it. And she had a great time. She felt much stronger. She came back. And when she finished college, she was able to read behind her majors in art and found that she liked writing and went to wrote to an MSA program at Columbia and is now in the middle of her first novel.
Karen: Wow, that’s an amazing story. Let’s give people that website for your daring project.
Gail: Oh, good. Its sheehydaringproject.com. It’s S, like Sam, H, double E, H-Y, and then D-A-R-I-N-G, and the project, P-R-O-J-E-C-T.com.
Karen: Where have you learned? I mean, the story you just told was incredible. What else are you learning about interviewing women about their daring moments? What themes are you picking up?
Gail: Well one of the main surprises is how many fears even the boldest women that we look up to have had to battle. Notably, Gloria Steinem, the icon of feminism. She was a colleague of mine back at New York magazine in the late ‘60s and the ‘70s. I thought I knew her very well. But it was only when I interviewed her for a story for the daring issue of Harper’s Bazaar, which will come out in November, that I learnt what kind of incredible trauma she went through as a young woman, who had a mother who was nonfunctional, that Gloria had to take care off while she was a child. And a father who was charming, but a vagabond, and left the family when Gloria was ten. She didn’t even get to go to school full-time until she was 11 years old.
So her whole life was colored by this experience and never wanting to have the responsibility for anyone else. Because it only reminded her of how bitterly she felt and failed as a child trying to take care of a sick mother. But she’s conquered it and conquered it over and over again. And when Gloria Steinem tells people that she never wanted to be the poster woman for the feminist movement, people definitely think “Oh well, that’s just false modesty.” But it’s true. She was terrified. When she started Ms Magazine and then, even though she had colleagues working on it with her, she told me “I was scared” – if I can use this word – “shitless all the time I was running Ms. Magazine.” But she kept on and that publication became kind of the script for women who were trying to master feminism. So I find that these fears that we often cover by looking confident are pretty deep in many woman.
Karen: I’d like to talk a little bit about your amazing career which is covered thoroughly in daring. What was your first assignment as a journalist?
Gail: Well, my first assignment I gave myself. I was working at the Herald Tribune, which was the petri dish for new journalism, and I was pregnant – five months pregnant. And I was afraid I was going to get fired. Because that was what people usually did in those days because they didn’t think you were going to stick around. And I went to the editor-in-chief of the newspaper and said “I’m going to be completely honest with you but I’m pregnant, but you can use that. I’m five months pregnant and that’s when the intervention of medical care and maternity exams is most useful. And if you don’t get maternity exams and aren’t followed for the last months of pregnancy, the incidence of infant mortality increases vastly. And we have a terrible infant mortality problem in the United States and, even worse, in New York City. So let me go on take out the role of a waitress working day-to-day as a single mom and I’ll see what kind of maternity care you get free in New York.” And he bought it.
And I did a series of three stories about all the maternity clinics that are in East Harlem and The Bronx and all over the place. And it really got a lot of attention. The city government stepped in. They began closing some of the worst maternity clinics and developing neighborhood clinics that people could actually get to, instead of having to go to a distant hospital. So I won an award for it. That was a nice confidence-builder.
Karen: I can imagine that. I wanted to take just a moment to remind our listeners that we are sharing highlights from today’s call on Twitter and you can follow along and join the conversation @Pennwomen, @Texaswomen and @Masswomen. So your first assignment as a journalist, Gail Sheehy, was a confidence builder. It was also a very bold way of turning something going on in your own life into a story that would resonate with other women. What was the hardest assignment you had as a journalist?
Gail: Well the first of the hardest assignments, there was many of them, was to go and cover Bobbie Kennedy’s presidential campaign. I’d never written a political story and this was proposed by Clay Felker, who was then already a rather famous editor of New York magazine. He had just started and he came to see me up in my 4th Floor walk-up on the Lower East Side, in a limousine that he’d come from the Four Seasons where he had the opening night party, and said “What do you know about politics?” And I said “Well, my father is a country club Republican, and my mother is a bomb-throwing Irish rebel, so what I know about politics is about arguing at the dinner table.” And he said “Well, then you’ll understand Bobby.” I said “Bobby who?” He said “Bobby Kennedy.” I said “Why would I want to understand-?” He said “I want you to cover him in Oregon and California.” I said “I’ve never written a political story. I can’t possibly cover Bobby Kennedy.” He said “Gail, everybody has to learn. The main thing you need to know about being a journalist”- and this is the best advice I ever got – “is don’t just write a whole lot of little stories. Write the story that everybody is talking about and give them the why.”
Well, I went out on the campaign and it was only a few days before he died, and he had to go up and down the Cascade Mountains in Oregon for a last trip. And he – nobody wanted to go with him. All the senior reporters said “No forget that.” There was a thunder storm. It was going to be a terrible trip. So I got on this tiny little plane with him. I got to sit next to him, with Freckles the dog at our feet, and I got to interview him. I couldn’t believe it. And we had a really deep interview, but the most important thing was, as we were approaching the airport the clouds descended and we were in complete milk fog. And all of a sudden something broke through and it was the nose of another plane heading straight towards us. And the pilots just dropped almost a thousand feet at once and the other two reporters on the plane shrieked. I couldn’t even get a sound out of my throat. And Bobby Kennedy, while we were falling, said “I knew Gene McCarthy was desperate. I didn’t think he was that desperate.” And we all laughed and said “My God, what a fatalist.” Thank God Bobby Kennedy was a fatalist. There had been so many deaths in his family. And that gave me the key to my story.
Karen: That’s amazing. If you could go back and interview one of your subjects again, whether that’s Bobby Kennedy, or Margaret Thatcher, or Hillary Clinton or any of the other remarkable people you’ve written about, who would it be? And what would you want to know from them?
Gail: Well, I could tell you right away. I would like to interview Hillary Clinton right now. She’s so guarded that there’s no chance. But what I would want to find out from her – and of course I wouldn’t ask her directly. But what I want to find out from her is does she have the fire in the belly to run for president? I know it’s what she’s wanted to do all her life, that’s what she’s been groomed for. It’s what she’s given up a great deal for and made herself the darling of the Democratic Party and what appears to be the shoe in for presidential candidate. But I don’t know if she has the fire in the belly. When she’s interviewed now, she says, when she’s asked, “Well, why wouldn’t you run? And she’ll say “Well, I have a really nice life now. I really like my life.”
In other words, she has money, she has fame, she has the highest approval rating of-, way beyond Bill Clinton, when she became Secretary of State. It’s dropping now, as it would for anybody who’s running for president. Because that’s the way our system works when you get shot at as a candidate. She’s a grandmother. She is 68 years old. She can run around the world as a director, along with her daughter, of the Clinton Global Foundation. Does she really need to be cut up, thrown out the window and vilified, and lies and all kinds of things spread about her for the next two years? And then get to be President when the world is blowing up? I don’t know. Does she really want to do that that much? Now she will do it, probably. Most likely, she will do it. But I don’t know if you can get elected unless you have the fire in the belly. That’s what I’d want to find out by interviewing her.
Karen: I think there are many, many people who would like to ask the same question and figure it out, as well.
Gail: Really? Wouldn’t that be an interesting story.
Karen: That would be a great story. You have dared throughout your life. You were embedded in a war zone as a journalist. You were an activist. As you mentioned, you also dared to be a single mother, while working fulltime. Where did that come from? Where did that daring spirit of yours come from?
Gail: Well, I think some of it is inborn. But I also think a lot of it comes from being allowed to challenge yourself as a kid. And there was one study that seems to back this up. When I was a kid in the late ‘50s, we didn’t have helicopter parents. They didn’t really much care, once you were ten years old, where you were on Saturdays, as long as you kept out of their hair and got home in time for dinner. So, I was able-, my grandmother gave me the opportunity to live out my dream, which was to follow a radio show that was called Grand Central Station: Crossroads of a Million Private Lives. And there were these tense psychological dramas, like Oh, Henry that were acted out. And I thought “Oh my gosh, I have to go to Grand Central Station. I have to see these fascinating lives and write about them.”
And so when I was in 7th grade, my grandmother kept my secret and let me go, gave me the money to go and call her if anything happened. Somebody would push me up the washboard train steps so I could get up as high as the steps were in those days. Going from the Mamaroneck, New York, 43 minutes to New York. Go up to the balcony of the Grand Central Station and look down on this melee of people crisscrossing like crazy. And I’d see one in a floppy hat and a man with dark glasses, and they come together and they seem to be whispering and I’d say “Oh, obviously, they must be Communists. They must be spies.” And I’d get out my little pencil and paper and scroll notes about them. And when I-, after I’d done that for a couple of hours, I’d take the train back, take my bike home and write stories. So that was-, the idea of being able to do something, and not get in trouble for it, and nobody knew about it, find out what another part of the world was like and make something of it, art, pretended it was art, was very confidence building.
Karen: Did that give you the bug? Did you decide as a child, “I am going to be a writer”? Did you look at any other careers?
Gail: You know, I never thought of it as a career. Because I thought writers don’t-, they just have to do that for fun, on the side. You have to actually go to work in some office to make any money.
Karen: Gail, I want to ask you about the early days of your magazine career when you joined New York magazine with a very charismatic editor, Clay Felker, who would later become your husband, and from whom you learned a great deal and you worked with on some of the most amazing stories of the time. Could you give us a sense of what it was like in the New York magazine newsroom in those days?
Gail: It was thrilling. Most of us were from the suburbs. We were fugitives from the suburbs in the late ‘60s and we wanted to get into the City and get into the gritty parts of the city the city and figure out what was really going on. Tom Wolfe was our captain. And I remember him, I met him first at the Herald Tribune, where we were both working and he had told me the Herald Tribune, “New York magazine is the Tijuana bullring of competitive male journalists. That you have to be brave. So those were my working order. And so I would just say outlandish ideas and he would always love them. And I was always doing stories about social change. The first bachelor were mothers, and many-, you know, the changes that feminism were brining and all the divorces that were going on.
But there were many other journalists who were joining in and we had just a great club. And once a week we would have editorial lunches, and everybody had to come prepared with at least two ideas. So you could hardly bare to eat because you were so nervous that your ideas were not going to be good enough. But then you would get all kinds of cross fertilization from the other writers at the table. And your ideas would get better, or you would find out you would be given a source. So we had an absolute ball. And there was always-, I think it was the first weekly city magazine ever in America. We were just pioneering a whole new form. But the deadlines were killing because we were trying to put out what’s essentially a monthly magazine that explains the why of things, on a weekly basis.
So there was a lot of yelling and screaming, and a lot of laughing, and a lot of pot smoking late at night when people would be in trying to finish off their deadlines. And it was-, it happened so fast and was so exciting that we didn’t realize what we were really doing. That it was a revolutionary magazine concept. And we were living in the golden era of magazines, which has been declining ever since. Not because of us, but just because of social change and the digital age.
Karen: I’d like to talk also about your book, Passages, which made you a household name and was a global bestseller. When was it published and why do you think it resonated so much with readers for such a long time?
Gail: It was 1976. and it was the epicenter of this earthquake of change gender. It was happening in the US, but it was also happening in other parts of the world, or it was beginning to bubble up. And here comes a book that gave people a new way of understanding their lives. [Unintelligible 00:21:50] therapist and what they had already figured out. But it gave them a way to say “Wait a minute, I’m not the only one. I’m feeling uncertain. I’m feeling – I’m bored. The defenses I’ve had don’t work anymore. I’m not quite satisfied with where I am in my life, or with my marriage, or with my career, or with not having children, but that’s okay. Now I can say I’m in a passage, and it’s probably because I’m in this stage of life. Or I’m in another stage of life where I’m much more contemplative. Does that mean I’m just slowing down? No, it means I’m in another stage of life.
And it was liberating to many people, men and women, who may have been trained to think that being safe, being set, being in kind of a corporate channel, being living in the suburbs, having x number of children, being married, having the mortgage, was the right way. And if you weren’t totally satisfied with that, forever, there was something wrong with you or your marriage or your work. But actually being able to change feeling that this was normal, that it was healthy, and that it was a way to grow, liberated many people.
Karen: Now, you’ve started a new online movement, as we discussed earlier, called the Sheehy Daring Project. This is an online movement. Tell us what it is and how women can participate.
Gail: The Sheehy Daring Project is my website in which I present stories of women, famous women and everyday younger women, who have dared in some way, small or large, as an inspiration to women to be more daring, and to see what the payoff is. And I’m inviting women to send me a little capsule of their most daring moments. And I will then call those who sound like they have a really good story, interview them and write their story and put it up online, so that it will be useful to others. So I hope people will go to Sheehy Daring Project and enter their stories. I want to hear from them.
Karen: Wonderful. So that’s www.sheehydaringproject.com. To hear more from Gail Sheehy, please to join us at the Texas Conference for Women on November 13, or at the Massachusetts Conference for Women on December 4th. This concludes today’s teleclass. Thank you so much, Gail Sheehy, and thank you all for listening today.
Gail: My pleasure.