1. While DARING: My Passages traces the path of Gail Sheehy’s life, it also is a fascinating insider’s account of the ways in which journalism has evolved from the 1960s to the present day. How different is the media world today from the world she describes? What changes have come about for the better? Has anything gotten worse? If you were a journalist and could pick any decade to “fall into” career-wise, which one would you choose? What stories or moments in history would you most like to cover (or have covered)?

2. As a journalist, Gail Sheehy was --- and still is --- fearless. “Why couldn’t a woman write about the worlds that men wrote about?” she asked herself early on and throughout her career. Do you think you would’ve had the guts to be a female reporter during a time when journalism was dominated by men? What qualities do you think she and other pioneers like Gloria Steinem possess that enabled them to court long-standing success despite the risks involved?

3. Though Sheehy enjoyed a short first marriage and a long-standing on-again, off-again relationship with visionary journalist Clay Felker that later culminated in marriage, she was a single mother and thriving career woman for much of her adult life. Throughout DARING: My Passages, she writes about her attempts to balance motherhood with a successful career. What do you make of the way she approached this struggle? How are the challenges she faced then different from those working mothers face in today’s society? If you were in Sheehy’s shoes, do you think you would have juggled career and motherhood as she did, or would you have given up one for the other?

4. Were you surprised to learn about the humble beginnings of a well-known publication such as New York? How about the publishing world’s now muckety-mucks like Nan Talese, Helen Gurley Brown and Gloria Steinem?

5. Nowadays, it seems everyone can have a hand in journalism through social media, keeping a blog, and submitting online reviews or opinion pieces. Keeping in mind Sheehy’s roots in New Journalism and her increasingly prestigious career, do you think what she does and how she rose through the ranks to achieve notoriety was more respectable or worthy of merit? Or do you prefer today’s version of freeform journalism where there are no hierarchies, and everyone can participate and nab their five minutes in the spotlight?

6. Margaret Mead was a mentor to Sheehy. Mead once said, “One child does not necessarily interfere with a woman’s producing important work. One child can always be put in a bureau drawer. It’s having two children that really changes a woman’s life.” Do you agree with Mead’s assessment? If you have children, does it interfere with your work? Would you say that having two instead of one makes any difference?

7. In her groundbreaking book, PASSAGES, the then-30-something Sheehy wrote, “Women can have it all, but not all at once.” In DARING: My Passages, she further expands on this statement by writing, “Young women, like young men in their twenties, need time to extend their education, try out different partners and career paths, survive failure and build resilience, before they are ready to balance the competing demands and delights of marriage, family, and career.” Do you agree with Sheehy’s assessment? Looking back on your life, has your opinion on this subject changes as you’ve journeyed through life’s stages?

8. On page 165, Sheehy laments that at 34, she hadn’t done enough. She was dissatisfied with her life. Given all that she had accomplished up to that point, what do you make of the indictment? Why do you think she felt this way? What role do you think privilege has in these feelings, if any?

9. When Sheehy got involved with Clay Felker, she was already a hard-working, driven, and independent woman. Yet she made the choice to move from her East Village apartment to the grandiose world of the Upper East Side at the beginning of their courtship. What do you think she gained? Gave up? Given that she had a child, do you think it was a smart move? How do you think her life would’ve been different if she had made a different choice?

10. Having the courage to take a leap of faith in order to enforce change is a prominent theme in DARING: My Passages. Sheehy writes, “When we come to a dead end, if we dare to make a major life change, we will grow from it. When one door closes, that makes room for another door to open.” Would you agree? On the flipside, isn’t said change only possible for those who are able to do so, whether to afford their own furnished apartment on the Upper West Side (like the one Sheehy rented during a “break” with Clay Felker) or forge a new path in other ways? Are financial constraints a factor, or is that just an excuse to stay in a non-working situation?

11. After the publication of her wildly successful book, PASSAGES, Sheehy began to research “pathfinders”: people who find unique paths to growth in physical, emotional, social, and spiritual dimensions of their lives during particularly difficult passages. She states that these people are willing to take risks, have handled important transitions in an unusual way, and have learned how to find true meaning and direction in their lives. Given these characteristics, would you describe yourself as a pathfinder? Why or why not? Are there others who are pathfinders in your life, and what makes them so?

12. Sheehy’s PASSAGES is one of the most influential books of all time. In it, Sheehy interviewed women about how they felt during various stages in life. One response she received was, “Why couldn’t I have been the sort of person who just settles down and doesn’t give anyone a moment’s trouble, meaning, have a baby and the whole thing. I didn’t want it, but felt I SHOULD have.” Do you relate to this statement? Why do you think so many women feel the conflict between having babies and pursuing their careers (aside from biology, of course)? What about women who forgo one in pursuit of the other? What are the “shoulds” in your life, and what is your approach to dealing with them?

13. Toward the end of DARING: My Passages, Sheehy writes that the most satisfying stage of women’s lives is when they are in their 50s --- at least this holds true for the majority of healthy women. If you are 50 or over, would you agree with her? If you are under 50, what do you think about this statement? If you had to choose a phase of life in which you thought you’d be happiest when you where 19, what age would that be? Has that idea evolved, as you have grown older?

14. DARING: My Passages is decidedly a book about a woman’s path to fulfillment in marriage, motherhood and career. Would you describe this as a “woman’s book”? Why or why not? Do you think men would find different value in reading it, or does gender not make a difference?

15. Sheehy has written 16 previous books and countless articles on love, family, sex, politics, social movements, global policy and more. Have you read any of her other books? If so, which was your favorite? How does her memoir compare to the others? If you were her editor for this memoir, were there sections where you would have used your red pen to edit out or embellish? Do you think she succeeded as a journalist and writer, turning inward to write about her life as a whole?