Ariel Levy’s new memoir begins with a description of disorientation. “For the first time I can remember, I cannot locate my competent self,” she writes. “In the last few months, I have lost my son, my spouse, and my house. Every morning I wake up and for a few seconds I’m disoriented, confused as to why I feel grief seeping into my body, and then I remember what has become of my life.” In the book that follows, Levy examines the choices that brought her to this point of collapse. Was she the agent of her own destruction? Did she ask too much of life?

The story of how Levy lost her son was first published in the New Yorker in 2013. A staff writer for the magazine, she had a miscarriage in a hotel room while on assignment in Ulaanbaatar, Mongolia, when she was 19 weeks pregnant. Her son was born alive, but did not survive; Levy held him in her hand as he died. She spent a night in the hospital, then returned home to New York with “a longing – ferocious, primal, limitless, crazed – for the only person I had ever made”.

The loss caused Levy to assess her life as a hubristic experiment gone awry. “I knew, as surely as I now knew that I wanted a child, that this change in fortune was my fault,” she writes. “I had boarded a plane out of vanity and selfishness, and the dark Mongolian sky had punished me.” A doctor assured Levy that it was not the flight that had caused the miscarriage, but a placental abruption, a rare condition possibly related to her age (she was 38). Still: “The future I thought I was meticulously crafting for years has disappeared, and with it have gone my ideas about the kind of life I’d imagined I was due.”

That life had balanced domesticity with the pursuit of intellectual and sexual adventure. By the age of 35, Levy was a homeowner with an organised linen closet and a writer at an elite magazine who travelled the world. She was married to a woman. She got pregnant via artificial insemination with a male friend, a co-parent who wanted “the love without the labour” of procreation. She had chosen her career as a writer for love instead of money, but felt comforted by the material wealth of her sperm donor, who was “not insignificantly” rich. As she put it, “I had managed to solve the Jane Austen problems that women have been confronting for centuries – securing a provider for your children, finding a mate to pass the time with, and creating a convivial home – in an entirely unconventional way.”

Levy defied convention, and then her life fell apart. The title of this inquiry, The Rules Do Not Apply, refers to both the before and the after – a life lived in defiance of restrictions led to a crisis with no user manual. The cause-and-effect relationship that Levy superimposes on her tragedy is brutal in its self-recrimination. She sees the misfortunes that befell her as punishment for having lived a decadent life. As she phrases it, in one iteration: “Anything seemed possible if you had ingenuity, money, and tenacity. But the body doesn’t play by those rules.” In another: “Daring to think that the rules do not apply is the mark of a visionary. It’s also a symptom of narcissism.” And in another: “We want a mate who feels like family and a lover who is exotic, surprising. We want to be youthful adventurers and middle-aged mothers. We want intimacy and autonomy, safety and stimulation, reassurance and novelty, coziness and thrills. But we can’t have it all.”

The marriage collapsed after the miscarriage. Levy had fallen in love with her spouse, Lucy, when she was in her late 20s and Lucy in her early 40s. Having babies was postponed so Levy could focus on her writing. “The important thing was to be married, and that I had already accomplished on my own smug, non-traditional terms,” she says. The couple bought a house on Long Island where they planted beds of hydrangeas and tomatoes and cuddled with their cat. Then Levy had an affair with an ex-lover. The marriage survived, but with damage, until Lucy’s secret life as an alcoholic became an unavoidable fact. The house was collateral damage.

This book is so stark and succinct it can be read in one afternoon, and Levy’s honesty is blistering. The first publication of the account of her miscarriage shredded through the middlebrow nicety of the New Yorker house style like a tornado through a cornfield. The expansion here disappoints only when it veers into what the feminist author Rebecca Traister has described as the “don’t forget to have a baby” school of literature. The joke being: as if you could forget. It is when Levy chides herself and her friends for having waited to try to get pregnant that she loses some authority. “One day you are very young and then suddenly you are 35 and it is Time,” she writes. For now, at least in the US, the calculation to delay pregnancy for many women is more likely to come from an instinct of self-preservation than self-absorption.

The compassion Levy does not give to herself is left to the reader, who will feel it on her behalf – at the honest moments, when she describes how it feels to be sexually attracted to both men and women, or in the unexpected correspondence she takes up with the South African doctor who treated her in Mongolia. While a magazine article has to adopt a tone of authority, here Levy allows herself to revise impressions of the people she has profiled with room for doubt or admiration, and her own narrative is interspersed with stories of reporting on the South African runner Caster Semenya, the rightwing American politician Mike Huckabee and the leader of a gang of lesbian separatists named Lamar Van Dyke.

The book ends on a note of uncertainty: “For the first time in my life,” Levy concludes, “I have no plan.” It offers a sign of hope: she sought to live an original life within the conventional boundaries of feminine success (marriage, motherhood). In the end, against all her plans and wishes, conventional domesticity eluded her. It’s an unwanted freedom, but one suspects she will use it well.

• Emily Witt’s Future Sex: A New Kind of Free Love is published by Faber. The Rules Do Not Apply is published by Fleet. To order a copy for £12.74 (RRP £16.99) go to bookshop.theguardian.com or call 0330 333 6846. Free UK p&p over £10, online orders only. Phone orders min p&p of £1.99.