Ada Calhoun Probes the Conflicts Facing Gen X Women in ‘Why We Can’t Sleep’

In her new book, Ada Calhoun poses the question we all feel too tired to ask.

Ada Calhoun
Ada Calhoun. Gilbert King

I felt seen. I believe this is a phrase appropriated and made popular by Millennials, but upon reading Ada Calhoun’s Why We Can’t Sleep, this encapsulated my overwhelming impression upon turning the final page. In her new book, Ada Calhoun poses the question we all feel too tired to ask. Unspoken as it may be, this question has touched a nerve; her book is enjoying its second week on the New York Times best seller list.

Born between 1965 and 1980, Generation X is now squarely middle-aged. Caught between the larger profiles and populations of Boomers and Millennials, Generation X quietly trudges along. While some of us are new parents, others are tending to aging parents—and some are juggling both caretaking roles. The last generation to grow up without the Internet, we enjoyed early adulthood in the shadow of 9/11 and the so-called death of irony. During the years in which we should have shored up our careers, we weathered recessions, busts, housing market and financial market fallouts.

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Generation X women carry the burden of our mother’s second wave feminist history and their expectations. After being told they could “have it all” and encouraged to live out the dreams they wished for themselves, Generation X women punish themselves for their failure to achieve a mythical work-life balance. Calhoun remarks in Why We Can’t Sleep, “We were an experiment in crafting a higher-achieving, more fulfilled, more well-rounded version of the American woman. In midlife many of us find that the experiment is largely a failure.” Our skewered sense of time and identity becomes less puzzling when you recognize that we are perpetually striving for the future while constantly aware of the past. It’s a condition that makes it incredibly hard to simply live in the moment. Constantly compromising and struggling to make ends meet, Generation X suffers from downward mobility. Generally speaking, we will be the first American generation to not surpass their parents’ incomes or lifestyles. Even without our current political chaos, there’s a lot that keeps us up at night.

Ada Calhoun recognized as much in herself. After publishing her second book, despite a happy home life and professional success, she found herself in debt to the tune of $20,000 after a string of scheduled freelance jobs, “evaporated.” Her shaky sense of job security kept her awake at 4 a.m. It became clear that she wasn’t alone.

After writing an essay for in 2017 titled “The New Midlife Crisis,” which identified a clear trend of anxiety plaguing Gen X women, Calhoun reflected in a phone call with Observer, “The piece really resonated.” Like her, many women were finding themselves unhappy with their lives yet incapable of admitting it. While she had written a lengthy magazine piece that held a mirror up to this condition, there was more nuance to capture and greater detail to explore.

“I used it as a starting point to take each of these areas that I covered and blow them up to make a book,” Calhoun notes in conversation. “I tend to over-report articles so going into the book, I already had a lot of material. There hadn’t been a lot of hope in the article—it had been relatively bleak—so I thought for the book, I wanted to add a section that’s more hopeful in terms of reframing your life, about narratives and what we can do.” With that motivation and audience as a starting point, Calhoun gained access to’s social media channels to construct Google docs of hundreds of people answering her questionnaire. “I could get in touch with people individually from there. I also wanted significant regional and racial diversity so if I found that I was lacking, I would target it. I’d look at message boards to find women talking to each other online and contact the ones who had good stories.”

At the opening of her book, Calhoun makes mention of the fact that she excluded lower income Generation X women who face a far more perilous struggle than middle to upper class women. There’s a distinct reason for that choice, which has to do with the guilt shared by women who dismiss their anxiety and unhappiness. She relays in conversation, “There were a lot of things that I didn’t expect going into this project, but one was the similarity of the language that women were using even in different parts of the country—even if they were atheists and fundamentalists in Texas. Two of the things they said was, one, ‘I’m so lucky. I have no right to complain.’ They would minimize their own experience. And the other thing was ‘What did I do wrong?’ No matter how many outward differences these women might have, they still blamed themselves if they weren’t doing better and they thought they were lucky and to complain was to be whiny.” When asked what surprised her the most, she confesses, “I was surprised that Generation X has had such bad luck. I think that the march of non-progress of downward mobility and the rise in costs was very validating. I found just getting through the month was really expensive. It seemed like it was it so much easier at other points in time—paying for college, paying for housing—and I found that to be true.”

The cover of Ada Calhoun's Why we can't sleep,.
Why We Can’t Sleep. Grove Atlantic.

Throughout the book, Calhoun draws out stories that speak to an overwhelming sense of panic. Her chapters turn from women torn between their desire to be a parent while also dreaming of landing a high profile position to the topics of dating in one’s forties and fifties, facing divorce, what feels like the betrayal of our bodies during perimenopause and menopause, and the lie of social media. Throughout the various chapters, Calhoun returns again and again to the historical context that brought us here and the added stress that masks itself as solutions.

Nailing the tension women feel when self-care becomes another item on our endless “to do” list, Calhoun remarks in her book, “Our problems are beyond the reach of ‘me-time.’ The last thing we need at this stage of life is self-help. Everyone keeps telling us what to do, as if there’s a quick fix for the human condition. What we need at this stage isn’t more advice, but solace.” Reaching that solace is a challenge we try to squeeze in between searching for childcare and hustling for more side gigs to make ends meet. While the advice comes from a genuine place, achieving that goal can feel like an economic luxury out of reach for many women.

Calhoun admits the struggle is real, noting over the phone, “I have mindfulness people after me now because, in an interview with the Toronto Star, I said, ‘Oh, now I have to be mindful, in addition to making dinner, cleaning my house, taking care of my parents and I’m supposed to revel in every second?’ No, I’d rather just bang it out and I think it’s one more pressure. If only we can really dwell in the moment or do enough yoga, somehow all of this is going to be easier. I don’t feel that’s going to work for all of us. For some people, sure, they may reach a higher level of peace where their lives are better but I think that when people are overwhelmed, telling them to do one more thing is just cruel.” To Calhoun, that’s just a reinforcement of the the idea that a woman’s condition is entirely her fault. That, she says, is a message they’ve already receivedloud and clear.

But the question remains: How do we forge institutional change when we’re all cobbling together various fixes, working around the system when what we actually need is something larger? And who has time to collectively organize? Calhoun steps back to say, “The first step is to really look at it and say that it is not sustainable for a lot of very tired women who are really stressed out to actually suffer. When women kept telling me, ‘No, I’m lucky, I’m lucky,’ I wanted to say, ‘but are you? Look at how hard your life is?’ Women too often see what they don’t have rather than what they do have; yet they keep saying how lucky they are. Where’s the balance between the two. There’s a lot of envy at play as well. Instead of recognizing the nuances of what we’re all collectively going through, we tend to cycle between feeling awful then feeling lonely. Social media only exacerbates the problem of feeling we’re the only ones soldiering through a crisis.”

In addition to the falsehoods perpetuated by social media, Calhoun wants to dispel another myth, “I think we get pitted against each other all the time. The ‘Mommy Wars’ was a total conspiracy. It’s not real. Then women who have kids or don’t have kids. I look at my friends and our generation is so spread out in terms of what we’ve done. I have friends my age with babies and others who have adult kids. It’s such a spectrum. We’re all trying to get what we can from a system that wasn’t built to support us so why do we see one another as enemies or different from one another? We’re all trying to get whatever we can.”

One way to combat these pervasive social perceptions is to put down our phones and listen to one another in person. It’s exciting to enjoy the success of connecting with readers through book sales, but Calhoun has found another point of pride. “Some people are telling me that they’re using the book to start a club, which is my dream come true. They use it to get together in person to talk about the book as a midlife crisis club. I think there’s no higher compliment than that because I do think that makes a difference.” Making time to meet up with friends is what brought Calhoun out of her own funk. “I starting this group, the Sob Sisters, with my friends Susannah Cahalan (author of The Great Pretender) and Karen Abbott (author of The Ghosts of Eden Park). [It] includes a really wide range of ages—from people in their 20s to people in their 60s, but a lot of middle-aged people. We all come together once a month in a room to talk about writing, hear from an editor or a writer with a new book out, have drinks, sit around. It’s been transformative for me and given me a real anchor.”

The consciousness raising groups of the 1970s have a lot in common with the Sob Sisters. “It’s similar,” reflects Calhoun. “I think our mothers and grandmothers got it. They were so smart and knew they needed community so they found one in various places. Whether it was a church group, a stitch and bitch, a consciousness raising group, they built it into their week that they would see other women and talk with them. We’ve worked that out of our lives to our peril.” Perhaps Generation X internalized the wrong impression of our mothers’ expectations. They wanted us to feel free to choose what we wanted rather than want it all. We needed more encouragement to talk these decisions out together. Why We Can’t Sleep offers a special call to mend these misunderstandings through connection rather than apply additional scrutiny to the problems at hand.

Ada Calhoun Probes the Conflicts Facing Gen X Women in ‘Why We Can’t Sleep’