FOR AS LONG AS self-help books have been around, highbrow readers have seen fit to sneer at them. When Samuel Smiles published the original of the genre, Self-Help, in 1859, one representative detractor called him “the arch-Philistine” and dismissed his book as “the apotheosis of respectability, gigmanity, and selfish grab.” A century and a half later, that tradition endures, resulting in a persistent two-way deficit: books about bettering your life don’t have many literary champions, and literary champions don’t have many books about how to better their lives.

Into this rift comes British author Sarah Bakewell with How to Live, an intellectually hefty book that restores both history and legitimacy to the project of trying to help ourselves. “How to cope with a friend’s death, how to work up courage, how to act well in morally difficult situations, and how to make the most of life”: problems like these, Bakewell reminds us, were the stuff of philosophy long before they were the ingredients of Chicken Soup for the Soul.

In fact, Bakewell’s book is so sincerely engaged with the question of how best to muddle through life that it takes a chapter or two to remember that what you’re actually reading is a biography of the great French essayist Michel Eyquem de Montaigne. And no sooner do you get your mind around this fact than you realize that there’s more. How to Live not only tells the story of Montaigne, the man; it also tells the story of (in Bakewell’s wonderful phrase), “Montaigne, the long party.” For more than four centuries, readers have crowded into the capacious chambers of the Essays to listen, laugh, think, thrill to, and argue with one of the greatest minds in history. It is that conversation, as much as the man who started it, that How to Live animates and explains. In sum, this book, like its subject, is expansive, genre-defying, and preposterously smart.

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Montaigne was born in 1533, to an aristocratic father with distinctly experimental ideas about child-rearing. Montaigne père promptly sent the boy away to be raised by peasants — not to disown him, but because he believed his infant son would absorb, in Bakewell’s words, “an understanding of commoners’ ways along with their breast-milk.” Once this phase of the experiment was over, the elder Montaigne swung dizzyingly in the other direction, summoning the toddler home and decreeing that his mother tongue would be Latin. Never mind that nobody’s mother tongue was Latin anymore; in Renaissance France, hiring a Latin tutor was like setting up a trust fund — a way to set your kid on the path to a swanky school and a lucrative career. The Montaigne family merely took the matter to its logical extreme, securing a tutor and then forbidding everyone in the household to speak to the boy in any other language.

This strange start in life explains m...