The Socrates Express: In Search of Life Lessons from Dead Philosophers

by Eric Weiner

There’s a difference. Information is a jumble of facts, knowledge a more organized jumble. Wisdom untangles the facts, makes sense of them, and, crucially, suggests how best to use them. As the British musician Miles Kington said: “Knowledge is knowing that a tomato is a fruit. Wisdom is not putting it in a fruit salad.” Knowledge knows. Wisdom sees. The difference between knowledge and wisdom is one of kind, not degree. Greater knowledge does not necessarily translate into greater wisdom, and in fact can make us less wise. We can know too much, and we can mis-know. Knowledge is something you possess. Wisdom is something you do. It is a skill and, like all skills, one you can learn. But it requires effort. Expecting to acquire wisdom by luck is like expecting to learn to play the violin by luck.

Most schools today don’t teach philosophy. They teach about philosophies. They don’t teach students how to philosophize. Philosophy is different from other subjects. It is not a body of knowledge but a way of thinking—a way of being in the world. Not a “what” or a “why” but a “how.”

It was not the meaning of life that interested them but leading meaningful lives.

Duty comes from inside, obligation from outside. When we act out of a sense of duty, we do so voluntarily to lift ourselves, and others, higher. When we act out of obligation, we do so to shield ourselves, and only ourselves, from repercussions.

“Our culture has generally tended to solve its problems without experiencing its questions.”

Of course. The inscrutable, inevitable Socrates. Philosophy’s patron saint. The King of the Question. Socrates didn’t invent the question, but he altered the way we ask them and, in turn, the answers they yield. You think and act differently because of Socrates, even if you know nothing about him.

Socrates ate little, bathed rarely, and always wore the same shabby clothes. He walked barefoot everywhere, even in the dead of winter, and with a strange gait, somewhere between a waddle and a swagger. He could go days without sleep, drink without getting drunk. He heard voices—well, a voice. He called it his daemon. “This began when I was a child,” he explained during his trial on charges of impiety and corrupting the youth of Athens. “It is a voice, and whenever it speaks it turns me away from something I am about to do, but it never encourages me to do anything.” Taken together, Socrates’s peculiar

They possess an otherness that borders on the alien. Even Marcus, a Roman emperor, felt like a misfit. Diogenes, a founder of Cynicism, was the ultimate oddball philosopher. He lived in a barrel, masturbated in public, and in general traumatized the good people of ancient Athens.

boats. They have too much at stake. Not philosophers. They’re outliers. Aliens. Socrates was a practitioner of “Crazy Wisdom.” Found in traditions as disparate as Tibetan Buddhism and Christianity, Crazy Wisdom operates on the premise that the path to wisdom is crooked. We must zig before we can zag. Crazy Wisdom means casting aside social norms and risking ostracism, or worse, to jolt others into understanding. The original shock therapy. No one likes to be shocked, and we often dismiss practitioners of Crazy Wisdom as more crazy than wise. Here is how Socrates’s student Alcibiades describes him: “He will talk of pack-asses and blacksmiths, cobblers and tanners, and he always seems to be repeating the same things so that someone who wasn’t used to his style and wasn’t very quick on the uptake would naturally take it for the most utter nonsense.” Yet, Alcibiades concludes, spend some time truly listening to Socrates and you realize it’s

anything but nonsense. “This talk,” he says, “is almost the talk of a god.”

For Socrates, the worst kind of ignorance was the kind that masquerades as knowledge. Better a wide and honest ignorance than a narrow and suspect knowledge.

The universe may be fascinating, but it’s not much of a conversationalist, and conversation was what Socrates craved the most.

Socrates couldn’t fathom why his fellow Athenians weren’t more interested in these kinds of questions, given their zest for improvement, be it a better way of making statues or practicing democracy. Athenians, it seemed to Socrates, worked tirelessly to improve everything—except themselves. That needed to change, he thought, and he made it his life’s mission to do so.

The examined life demands distance. We must step back from ourselves to see ourselves more clearly. The best way to achieve this perspective is through conversation. For Socrates, philosophy and conversation were virtually synonymous. Socrates talked to all sorts of people: politicians, generals, craftsmen, as well as women, slaves, and children. He talked about all sorts of subjects, too, but only important ones. Socrates wasn’t much for chitchat. He knew life was short and he wasn’t about to waste one second of his allotted time on trivialities.

By talking to others he learned how to converse with himself.

As Voltaire said, the best judge of a person is not the answers they give but the questions they ask.

The child’s questions irk us not because they are silly but because we are incapable of answering them adequately. The child, like Socrates, unmasks our ignorance, and while that may be beneficial in the long run, in the short run it’s annoying. “If you do not annoy anyone, you are not a philosopher,” says Peter Kreeft.

The goal was not to humiliate but to illuminate, to facilitate a kind of intellectual photosynthesis. Socrates as gardener. He loved nothing more than “planting a puzzle in a mind and watching it grow.”

Philosophy is definitely interested in the destination,

but the journey can’t be rushed. That is the only way to ensure you arrive not merely at clever answers but “answers of the heart.” The other kind, answers of the head, are not only less satisfying but, in the deepest sense, less true. Arriving at answers of the heart demands not only patience but a willingness to sit with your ignorance. Staying with the doubt, the mystery, rather than rushing to solve the problem, to check off another item on your endless to-do list. This takes time, and courage. Others will mock you. Let them, says Jacob Needleman, and Socrates, too. Ridicule is the price of wisdom.

A good question prompts not only a search for answers but a reevaluation of the search itself. A good question elicits not a clever reply but no reply at all. From ancient times, long before Socrates, Indian sages have practiced brahmodya, a competition where contestants aim to articulate absolute truth. The contest always

ends in silence. As author Karen Armstrong explains, “The moment of insight came when they realized the inadequacy of their words, and thus intuited the ineffable.”

This is exactly what Socrates aimed to induce: a state of ruthless self-interrogation, questioning not only what we know but who we are, in hopes of eliciting a radical shift in perspective.

Corollary Number One: The examined life that doesn’t produce practical results isn’t worth living. Contemplating one’s navel has its pleasures but it is far more satisfying to see results, a better navel. Eudaimonia, the Greeks called it. Often translated as “happiness,” the word signifies something larger: a flourishing, meaningful life. Consider, as the contemporary philosopher Robert Solomon suggests, two people. One has an elaborate theory of generosity, while the other does not. “Generosity just flows from him, unthinkingly, as water flows from a fountain.” The second person is clearly leading the exemplary, meaningful life. Corollary Number Two: The unexamined life may not be worth living, but neither is the overexamined one. “Ask yourself if you are happy and you cease to be so,” said the British philosopher John Stuart Mill, articulating the Pleasure Paradox (also known as Paradox of Hedonism). The more we try to seize happiness the more it slips from our grasp. Happiness is

a by-product, never an objective. It’s an unexpected windfall from a life lived well.

He was philosophy’s first martyr. After his trial, his fate sealed, he gathered with a few of his followers. They were heartbroken, but not Socrates; he remained sanguine, and coyly opaque, until the end. “And now it is time to go, I to die, and you to live, but which of us goes to a better thing is unknown to all but God,” he said. Those are excellent last words, and indeed that is how many a biography of Socrates ends. There’s only one problem. They were not the philosopher’s last words. Plato, in a dialogue called Phaedo, tells us what transpired during Socrates’s final minutes.

“Crito,” says Socrates, speaking to his friend. “We owe a rooster to Asclepius; make this offering to him and do not forget.” “It shall be done,” replied Crito. “But have you anything else to say?” There was no reply. Socrates was dead.

What to make of this seemingly pedestrian exit? For centuries, scholars have pondered that question. Some interpret Socrates’s last words darkly. At the time, roosters were offered to the god of healing, Asclepius, so perhaps Socrates was saying life is like a disease we must cure. Or maybe it was Socrates’s way of calling us back down to earth, even as he ascended to heaven. Maybe he was reminding us, as we grapple with life’s big questions, not to forget the small stuff. Don’t overlook your obligations as a citizen and a friend. Be a person of honor. If you owe someone a rooster, give him a rooster. There’s a simpler and less profound possibility: the hemlock had begun to take effect, and an addled Socrates was mumbling gibberish. No one knows for certain, ...

planting one more puzzle in our minds. One more quest...

Jean-Jacques Rousseau was a man of multitudes: philosopher, novelist, composer, essayist, botanist, autodidact, fugitive, political theorist, masochist. Most of all, he was a walker. He walked often and he walked alone. Yes, a stroll with a close friend has its pleasures, as do walking clubs, but at its heart walking is a private act. We walk by ourselves and for ourselves. Freedom is walking’s essence. The freedom to depart and return when we wish, to meander, to, as Robert Louis Stevenson put it, “follow this way or that, as the freak takes you.”

Walking saved Rousseau’s life. It also killed him.

He ran frantically, but it was no use. He was too late. Sleeping outside the city walls that night, Rousseau vowed never to return to Geneva. From that day, he led a nomadic life, traveling ceaselessly, and almost always by foot.

Walking enabled Rousseau to escape the eyes of others. He was shy. Severely nearsighted, an insomniac like Marcus, and with a lifelong urinary problem (eventually diagnosed as an enlarged prostate) that required frequent visits to the toilet, he avoided social contact whenever possible. Throughout his life, he imagined people were staring at him. It probably didn’t help that he had an odd compulsion to expose his rear end to strangers. Rousseau was an avowed masochist who enjoyed a good spanking, like the one he received as a delinquent schoolboy. “I found in the pain, in the shame even, a mixture of sensuality

that left me desiring more,” he writes in his memoir, among the first to contain such personal, and salacious, details. Walking was an obvious fit with Rousseau’s philosophy. He advocated a return to nature, and what is more natural than walking? Natural, that is, for most of us.

Rousseau’s philosophy can be summed up in four words: nature good, society bad. He believed in the “natural goodness of man.” In his Discourse on Inequality, he paints a picture of man in his natural state, “wandering in the forests, without industry, without speech, without domicile, without want and without liaisons, with no need of his fellow-men, likewise with no desire to harm them.” Nobody is born mean-spirited, petty, vindictive, paranoid. Society makes them that way. Rousseau’s “savage man” lives in each moment with no regrets about the past or worries about the future.

No wonder so many philosophers walked. Socrates, of course, liked nothing more than strolling in the agora. Nietzsche regularly embarked on spirited two-hour jaunts in the Swiss Alps, convinced “all truly great thoughts are conceived by walking.” Thomas Hobbes had a walking stick custom made with a portable inkwell attached so he could record his thoughts as he ambled. Thoreau regularly took four-hour treks across the Concord countryside, his capacious pockets overflowing with nuts, seeds, flowers, Indian arrowheads, and other treasures. Immanuel Kant, naturally, maintained a highly regimented walking routine. Every day, he’d eat lunch at 12:45 p.m., then depart for a one-hour constitutional—never more, never less—on the same boulevard in Königsberg, Prussia (now Russia). So unwavering was Kant’s routine that the people of Königsberg set their watches by his perambulations. Good walkers, all of them. None, though, compares with Rousseau. He’d

regularly walk twenty miles in a single day. He once walked three hundred miles from Geneva to Paris. It took him two weeks. For

The walking philosopher gives the lie to one of the discipline’s greatest myths: that it is a mental pursuit wholly divorced from the body. From Archimedes’s eureka moment in the bath to Descartes’s masterful fencing to Sartre’s sexual escapades, philosophy has a swift corporeal current running through it. There are no disembodied philosophers, or philosophies. “There is more wisdom in your body than in all of your philosophy,” said Nietzsche.

Respond to adversity, real or imagined, not with self-pity or hand-wringing, but simply by starting over. Viewed this way, life no longer feels like a narrative gone awry, or a botched ending. None of that is real.

There are no endings. Only an infinite chain of beginnings.

In late October 1776, Rousseau was navigating a narrow Parisian street, on his way home after a long walk, when, as the biographer Leo Damrosch relays, “a nobleman’s carriage came hurtling toward him, flanked by a huge, galloping Great Dane. He was unable to dodge in time, the dog bowled him over, and he fell hard on the cobblestone street, bleeding profusely and unconscious.” Rousseau likely suffered a concussion and neurological damage. He never recovered fully. Less than two years later, Jean-Jacques Rousseau returned from his morning walk, collapsed, and died.

Rousseau’s legacy is vast. It includes Hallmark cards, Hollywood tearjerkers, heart-shaped emojis, and tell-all memoirs. If you’ve ever said, “I need a good cry,” you can thank Rousseau. If you’ve ever said, “Use your imagination,” you’re being Rousseauvian. If, in the heat of an argument, you’ve actually uttered the words “I don’t care if it makes no sense, it’s how I feel,” Rousseau is your man. If you’ve ever answered heartbreak with a long and angry walk, Rousseau. If your spouse has ever dragged you on a ten-mile trek on a damp, cold day, because “it will be good for you,” you can thank, or curse, Rousseau. Because of him, we think and feel differently, and we think about our feelings differently.

The Jewish theologian Abraham Heschel described the Sabbath as a “sanctuary in time.” Walking is a sanctuary in motion. The peace we experience with each step adheres, and it conveys. Portable serenity.

Thoreau was born in Concord and, except for his time at Harvard and a brief (and unhappy) stint in New York, lived his entire life here. Thoreau loved Concord. Friends tried to convince him to see Paris, but he demurred. Even when he did travel, to Maine and Canada, he took Concord with him. “I carry Concord ground in my boots and in my hat—and am I not made of Concord dust?”

Thoreau, I think, was less yogi and more sannyasi. In Hindu tradition, a sannyasi is someone who, having discharged his familial obligations, relinquishes all material goods and retreats to the forest to pursue a purely spiritual life.

Henry David Thoreau, hero of Walden, beloved icon of American lore, apostle of environmentalism, giant of letters, was something of a jerk. Everyone who knew him said so. Thoreau possessed “a certain

iron-pokerishness, an uncompromising stiffness in his mental character,” said Nathaniel Hawthorne. Others were less kind. “Thoreau was literally the most childlike, unconscious and unblushing egotist it has ever been my fortune to encounter in the ranks of manhood,” said Henry James Sr., father of Henry James the novelist and William James the philosopher. The harshest criticism centered on Thoreau’s alleged hypocrisy. There he was pretending to live alone in the woods, self-sufficient, while sneaking off to his mom’s for pie and laundry service. It’s true. Thoreau wasn’t nearly as isolated at Walden as many believe. He regularly made the half-hour walk into town, not only for Mom’s home cooking but to visit the local post office or coffee shop. So was Walden a ruse? Have ninth graders nationwide been hoodwinked?

I don’t think so. Thoreau never claimed to have severed all ties with society. He doesn’t conc...

the visitors he received at his cabin. (Walden contains a chapter called “Visitors.”) As one Thoreauvian tells me, Walden isn’t a book about a man living in...

Everyone who met Thoreau commented on his appearance. Some remarked on his nose, prominent and Roman, “a sort of interrogation mark to the universe”; others his mouth, “uncouth and somewhat rustic”; or his hands, “strong and skillful.” Others remarked on Thoreau’s eerily acute senses, like his keen ear (“He could hear the most faint and distant sounds”) and acute sense of smell (“No hound could scent better”).