Someone once asked me if I was ever tempted to revisit a character or a storyline from one of my novels. I could honestly say I hadn’t, that it sounded like work, something I’ve tried hard my entire life to avoid. It also sounded boring, which, for me, is even worse. How can the reader be expected to care if the author doesn’t?

This changed after I wrote Why Not? Fifteen Reasons to Live, a collection of essays completed after enduring a deep depression brought on by finishing a long, difficult novel amidst the debilitating symptoms of obsessive-compulsive disorder, a disease I’ve suffered from all of my adult life and which tends to manifest itself most perniciously when I’ve embarked upon an engrossing project. (If nothing else, it’s a reminder of life’s ongoing irony: what tends to make me happiest also has the capacity to make me sick.) How to Die: A Book About Being Alive isn’t a sequel to Why Not? Fifteen Reasons to Live—a better diet, more exercise, and the correct dosage of the right medication have helped me remain as psychologically healthy as possible—but, rather, a continuation of the conversation begun in the latter book’s final chapter: Death. A conversation with whom? With myself, of course.

That I graduated with High Distinction with a degree in philosophy says less about my analytical reasoning skills or deep knowledge of any particular thinker or branch of philosophy than it does about my desire at the end of my undergraduate career to complete my degree so I could do something else. Simply put, philosophy—which from as far back as high school had seemed the zenith of human activities—had become a bore (there’s that word again). There’d been plenty of inspired and inspiring books encountered along the way—Pascal’s Pensées, Simone Weils’ Gravity and Grace, Martin Buber’s I and Thou, nearly everything written by Nietzsche—but, I came to learn, these works and others like them weren’t considered “real” philosophy by the academic community. Instead, they were dismissively lumped together as “wisdom literature”: at best, entertaining belles lettres; at worst, artsy-fartsy blather and bluster. A “real” philosopher was someone like Hegel, who, like the majority of his professorial brethren, wrote for other professors in a language seemingly created to deter comprehension about subjects as far removed from the everyday philosophical questions and concerns of most human beings as the ugly, ungainly style they employed was from lucid, illuminating prose. As it is with music, so it is with philosophy: if it doesn’t swing, it’s hard to understand the words. Or care.

One of those writers of “wisdom literature” I discovered during these years was Montaigne, someone I continued to enthusiastically read long after I’d decided that fiction was a better (and much more enjoyable) way of taking reality’s temperature. Pascal, Weil, Buber, Nietzsche, et al. were almost always interesting and often eloquent, but there was usually the unmistakable imprint of argumentation on their work. Since they were, after all, philosophers, this was understandable, but Montaigne was a different kind of reading experience. Although he offered opinions on virtually every subject imaginable (drunkenness, mortality, reading, sleep, friendship, anger, virtue, the art of discussion, experience, fame, pedantry, idleness, vanity, praying, cowardice, et cetera), these ideas weren’t the only fruit of his labours. Often, they were the least compelling part. Montaigne was born and remained a Catholic, but his ruminations on religion and humankind’s place in the universe, for example, were just that: an unflappable, unhurried exploration of every aspect of whatever subject happened to interest him, whether that led him into profundity, confusion, or even contradiction. Montaigne’s biographer and one of his finest translators, Donald Frame, described Montaigne’s style as “free, oral, informal, personal, concrete, luxuriant in images, organic and spontaneous in order, ranging from the epigrammatic to the rambling and associative.” One of the many pleasures of reading Montaigne is the sense that one is not so much reading a book as simply listening to an amiable, amusing, intellectually ecumenical human being thinking aloud about a variety of subjects that interest him, ultimate conclusions and logical consistency be damned. As befits the originator of the modern essay, Montaigne wrote foremost to find out what he thought, and his readers are invited along to listen in while he does so. Maybe best of all, Montaigne is good company.

He was also a dedicated amateur classicist, the very best kind of aficionado (he read and reread Horace and Cicero and Virgil and Ovid and Lucretius and others not to become or to appear learned, but because these ancient authors continued to stimulate and sustain him). His famous tower in Bordeaux, where he retired to ponder life and compose his essays, were packed with volumes by these cherished authors for the same reason that the home of the early eighteenth-century Scottish poet James Thomson was similarly stocked: “To cheer the gloom / There studious let me sit, / And hold high converse with the mighty dead.” Montaigne’s work is embroidered with the best that had been thought and said by these mighty dead, and he himself anticipated a possible objection to his literary method: “[S]omeone might say of me that I have here only made up a bunch of other people’s flowers, having furnished nothing of my own but the thread to tie them.” But Montaigne’s point of view is rarely overwhelmed by these other voices, which only serve to embellish and illuminate the essayist’s own thoughts and feelings. Nearly five hundred years of writers who have been inspired by, and attempted to emulate, his method may not have been as successful (myself included, utilizing many favourite long-deceased authors of my own who weren’t even born when Montaigne was alive and composing his essays), but that’s one of the reasons one keeps writing. Maybe next time you’ll get it right. Or at least closer to what it’s supposed to be.

If How to Die: A Book About Being Alive is supposed to be anything, it’s an examination of death (what it is and how we think about it) counterbalanced by a spirited rebuttal from life. When I told a friend I was writing this book, she replied, “What do you know about death?” (Meaning, I believe, both of my parents were still alive and my wife and I were healthy and happy.) All I could think to answer was, “As much as anybody who hasn’t died yet, I guess.” Additionally, an odd thing happens once one reaches the mid-century mark: people start to die. Not just any people, either, but people you know well and sometimes even love: colleagues, friends, family. And people you don’t know but have known all your life anyway: the sports and musical heroes, the movie actors and newsmakers of our youth and early adulthood, most of whom, even before they die, slowly fade from public consciousness (only to be replaced by new, younger icons who will, in time, endure their own eclipse as well.) Favourite restaurants and bars and businesses, too, begin to disappear with regularity, along with things less brick-and-mortar tangible but no less significant. When I moved to Toronto thirty-five years ago (35? No, it can’t be, do the math again—wow, yeah, 35), Toronto meant Queen Street West second-hand book buying and dive-bar slumming and Citytv; it meant Maple Leaf Gardens and the Brunswick House; it meant seven (count ’em, seven) repertory theatres. Now, what used to be Queen Street Cool is chiefly a shopping destination for 905ers visiting the city for the afternoon, Citytv is a media conglomerate’s neutered facsimile of what it once proudly, independently was, Maple Leaf Gardens is a Loblaws, and the adored Brunny—scene of so many Bacchanalian stunts and shenanigans—is a Rexall, and most people I know (myself included) get their movies on Netflix or via other streaming services, eliminating the need to ever leave the house. No doubt there are new second-hand bookstores and charmingly sleazy bars, new ways the city is electronically connected and sees itself, new ways of being what it means to be a Torontonian, but it’s unlikely I would know about them. Why would I? It’s not really my city anymore. One generation passeth away, another generation cometh, and ain’t that a drag.