"Anything worth doing," G.K. Chesterton wrote, "is worth doing badly." The aphorism, offered as epigraph to Manhood for Amateurs, is Michael Chabon-worthy for its wit and embrace of absurdity. The author even recasts the sentiment to suit his theme: "A father," he notes, "is a man who fails every day."

A father, Chabon reports elsewhere, is also a man aware of his own inconsistency. Railing against the Captain Underpants books for children, he grants that his dislike of this particular generation of pop "crap," while fondly recalling his own variety of the same phenomenon, leaves him open to charges of hypocrisy. "I'm a father," he says. "Being a hypocrite is my job." His four kids might well nod in agreement.

The various roles and functions of the "husband, father and son" that is Michael Chabon preoccupies Manhood for Amateurs. Though being pitched as the prolific U.S. novelist's first complete work of non-fiction – the essay collection Maps and Legends was published in 2008 – the text is actually composed of 39 short personal essays, many of which originally appeared in magazines.

Regardless of its origins, the book reads well as a whole – so long as the whole in question is Chabon's singular and remarkable sensibility. No how-to advice or self-help directives are forthcoming. Quite the opposite: As the title suggests, Manhood for Amateurs asks its questions about the contemporary male at the point where, in a sense, expectations of having any answers end.

The majority of the 39 forays into "amateur" manhood are hilarious – line for line, Chabon is one of the funniest writers working today – and all of them contain insights. A few are outright pioneering, their brevity notwithstanding.

The Cut mulls over the circumcision ritual and secular parenting. The Wilderness of Childhood meditates on the "significant shift in our idea of childhood" that has left, in the view of the follow-up essay, "no corner, no alleyway, no space anywhere in their lives that was free of adulthood supervision, adult mediation, adult control."

Then there is Burning Women, a surreal glimpse into the derangement of desire. It narrates the story of an affair between author's divorced mother and a local Lothario, and of a conversation between the teenaged Chabon and another woman, jilted by the same man, who waits in a car outside a house in suburban Maryland. "And tell him I had fun last night chasing him all over town," the "burning woman" says to the teenager.

Line for line, as readers of the novels The Amazing Adventures of Kavalier & Clay and The Yiddish Policemen's Union will attest, Michael Chabon is also a blazing stylist. His prose is elegant, alert and no less inclined than his imagination to follow a notion, a riff, even simply a cadence, wherever it leads him. But that is how all literary prose should be, a writer's voice being no more – or less – than how he perceives the worlds around, and within, him.

In the case of Chabon, that voice is intensely self-aware. The divorce of his parents and his "cool customer" single mother are only two of the private details up for discussion in Manhood for Amateurs. Other essays explore his own sexual awakening at 15 with a much older woman and a disastrous first marriage.

Nothing, it seems, is too raw or intimate. Some may find Chabon's depictions of himself as a domesticated creature – he cooks and bakes; he praises his wife as the real warrior; he speaks of the emotional presence needed to be a good parent – irritating, a clammy claim to membership in the club of the kinder, gentler contemporary male. Several of the essays are certainly the more affecting for their underlying emotional frankness, a tonal range, it is worth noting, that fellow writerly students of manhood, including one as likewise probing (if far darker hued) as Martin Amis, either won't attempt or can't pull off.

But debates over whether Chabon's persona in Manhood for Amateurs is generous and courageous or trendy and smug are irrelevant to the book's larger impulse. Some four centuries ago, French writer Michel de Montaigne published his Essays. By doing so, he initiated the slow, steady revolution in how Westerners both view, and employ, their own identities to understand their societies and times. "I am myself the matter of my book," Montaigne famously admitted of the first volumes.

He then added a very Chestertonian, or Chabon-like, disclaimer. "You would be unreasonable," he wrote in 1580, "to spend your leisure on so frivolous and vain a subject." Montaigne meant, of course, the reverse; his essays were interesting precisely because their subject was willing to expose his contradictions and limitations; to be fully, richly, even foolishly human on the page.

Michael Chabon's big-brained, bigger-hearted essays are of similar high, humane ambition.