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Each has something important to teach us. Each walked the path of virtue in a way that we must learn from.

The word “stoic” in English means the unemotional endurance of pain. Yet even a cursory look at the stories of these (mostly) men proves an enormous difference between the expectations of that lowercase stoicism and the realities of the philosophy, uppercase Stoicism. Stoicism is a vibrant, expansive philosophy filled with people who loved, who grieved, who strove, who fought bravely at close range in the great battles of history, who raised children, who wrote important works, who stood tall, who believed, and who lived. In their own time, these philosophers resisted the stereotype of lowercase stoicism, that they were unfeeling beasts of burden who suffered through life and looked only inward.

The Stoics were never simply resigned to the current state of things, accepting without objection the injustices of the world. Rather, they formed the most ardent “Resistance” to the tyranny of Julius Caesar, Nero, and others in the ancient world, even influencing popular democratic reforms. Just as Stoicism was the “stern nurse of heroes during the first century of the Empire,” to borrow historian Richard Gummere’s expression, it would play a similar role for many centuries after, including inspiring the leaders of the American Revolution as well as patriots like Thomas Wentworth Higginson, who led a black regiment for the Union cause in the Civil War (and was a translator of Epictetus). The Stoics have always been people who bled and died for change, whether it was appreciated or successful or not.

“I know,” Seneca wrote in 55 AD in a book on mercy written for the young emperor Nero, “that the Stoics have a bad reputation among the uninformed for being too callous and therefore unlikely to give good advice to kings and princes: they’re blamed for asserting that the wise man does not feel pity and does not forgive. . . . In fact, no philosophical school is kinder and gentler, nor more loving of humankind and more attentive to the common good, to the degree that its very purpose is to be useful, bring assistance and consider the interests not only of itself as a school but of all people, individually and collectively.”

The structure and style of these pages are inspired by Plutarch, one of the great biographers of history and, as it happens, both a chronicler and a critic of Stoicism.* We will be presenting to you overlapping but independent biographies of all of the major Stoic figures. The aim is to give you a rich resource you can turn to over and over again—as millions of readers of The Daily Stoic and The Obstacle is the Way have done for years now.

We have presented each of the Stoics through the lens of a defining characteristic or role they played in the history of their philosophy. You’ll meet Porcia the Stoic Iron Woman, Diogenes the Diplomat, Antipater the Ethicist, and Zeno the Prophet. We want to leave you not only with some facts about these figures, but with a fuller sense of their essence and the aspects of their lives that teach us the most about the art of living.

Our aim in these pages is not to achieve strict scholarly accuracy—which is impossible after so many centuries—but to elucidate the moral lessons that can be drawn from the lives of these complicated figures. For many of the early Stoics we turn to Diogenes Laërtius—the so-called “night watchman of the history of Greek philosophy.” His classic work, Lives of the Eminent Philosophers, compiled in the third century AD, is at times contradictory, offering what is clearly a mix of collected facts and fictions. But it is also filled with beautiful insights and stories. Diogenes cared as much about the personal as the philosophical, and that’s why his observations resonate in ways that other ancient scribblers and critics do not.

Because of the proximity of the later Stoics to political power in the Roman era, their names appear in the classic histories of Tacitus, Suetonius, and Dio Cassius, often with admiration where they lived up to their ideals (such as Tacitus’s accounts of the deaths of Thrasea and Seneca), or with derision where they failed them (such as Dio Cassius’s account of Seneca’s questionably accumulated wealth). Pliny, Strabo, Athenaeus, Aulus Gellius, and others shed additional light on the lives and teachings of the Stoics. Later, Christian writers such as Justin Martyr, Clement, Origen, Tertullian, Eusebius, Jerome, and Saint Augustine, who all learned so much from many of the Stoics, also help to bring their lives into focus.

In other cases, we rely on the accounts of writers like Cicero or on the Stoics themselves for information. Cicero, who identified as a member of the skeptical Academy and kept busy climbing to the top of Roman politics, nevertheless dedicated a huge chunk of his life to a deep immersion in the history and doctrines of the Stoics who preceded him, and through his effort we have access to many sources long since lost. Seneca is another equally valuable source, as he not only crafted new writings on Stoicism but filled them with a wealth of quotations and anecdotes about his Stoic predecessors we’d otherwise not have. It is these intersections that are most interesting, even if we don’t always have other confirming documentation, because they show us how the Stoics influenced each other, and how moral tales—like the one generations of Americans taught their children about George Washington and the cherry tree—can demonstrate important lessons regardless of veracity.

What the Stoics were after, what we remain interested in to this day, were lights to illuminate the path in life. They wanted to know, as we want to know, how to find tranquility, purpose, self-control, and happiness. This journey, whether it begins in ancient Greece or modern America, is timeless. It is essential. It is difficult. Which is why we ask, as the Stoics asked: Who can help me? What is right? Where is true north?

“You’ve wandered all over,” Marcus Aurelius wrote to himself in Meditations, “and finally realized that you never found what you were after: how to live. Not in syllogisms, not in money, or fame, or self-indulgence. Nowhere.”

If philosophy is anything, it’s an answer to that question—how to live. It’s what we have been looking for. “Would you really know what philosophy offers to humanity?” Seneca asks in his Moral Letters. “Philosophy offers counsel.”

It will be your job, after you read these pages, to heed this counsel, and to struggle with what Seneca described as the most important job of a reader of philosophy—the act of turning words into works. To turn the lessons of the lives of the men and women who came before us, their living and their dying, their succeeding and their failing, into actions in the real world.

For it is this, and nothing else, that earns one the title: Philosopher.

ZENO THE PROPHET (ZEE-No)

Origin: Kition, Cyprus

B. 334 BC

D. 262 BC

The story of Stoicism begins, fittingly, in misfortune.

On a fateful day late in the fourth century BC, the Phoenician merchant Zeno set sail on the Mediterranean with a cargo full of Tyrian purple dye. Prized by the wealthy and by royalty who dressed themselves in clothes colored with it, the rare dye was painstakingly extracted by slaves from the blood of sea snails and dried in the sun until it was, as one ancient historian said, “worth its weight in silver.” Zeno’s family trade was in one of the most valuable goods in the ancient world, and as it is for many entrepreneurs, their business was on the line every day.