The Cautionary Matrons

I asked Caryne why she thought our mentors have taken to enjoining rather than encouraging us. She said she had to think about it and rang me a few days later.

“They are the first generation of women who were presented with choices,” she said. “I think they are in the process of reflecting on a half-century of existence and are realizing that ‘having it all’ was really a lie. Sometimes I think the idea of ‘having it all’ can almost be more disempowering than ‘having it all’ because one is never allowed enough time or energy to excel in one area of their life.”

When confronted with grim advice, some young women go on the offensive. Said Jenny of her Cautionary Matron: “I think there is an element of jealousy there. If she can go back and do it over again, she would. But she can’t and I’m here so …”

Ms. Gottlieb had a response to this: “I think it’s part denial and part arrogance. I get it because I used to be that way in my 20s. I wanted the fairy tale. I thought that I deserved to have it, that it was my inalienable right! So that’s the arrogance, and the denial is that they simply can’t acknowledge that they, too, could become these older regretful women who wished they knew what was important in love earlier on. We’re not envious—we’re wiser.”

Ms. Wurtzel echoes this sentiment, writing in her Elle piece: “Age is a terrible avenger. The lessons of life give you so much to work with, but by the time you’ve got all this great wisdom, you don’t get to be young anymore.” And later: “Oh, to be 25 again and get it right.”

When I contacted Ms. Wurtzel, hoping for an extra pearl or two about how I, as a 25-year-old, might learn from her mistakes and “get it right,” she emailed that she “didn’t have an audience in mind when I wrote it, but if anything I was thinking in terms of people who could relate to it, not so much people who could learn from it.” She also backpedaled a bit from her cautionary stance. “Of course, I’m 42 and I’m not married, but I don’t feel sorry for myself. … It’s not that I’m not sad sometimes, but I’m definitely not sorry.”

Perhaps. But then there’s this part in her piece about her love life today: “Dating this person for three months, that one for a few weeks, sometimes longer. They come, they go, someone is always coming as someone else is going; it’s not like there’s no one, but it’s all so lonely.”

When Jenny—already fearful about turning 32, thanks to her personal Cautionary Matron—read Ms. Wurtzel’s article, she emailed me the following: “Ugh. Now I am going to sit, coma-like, on the sofa and contemplate my impending decay. Great.”