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He would have easily seen himself in Canus’s shoes, for he too walked the razor’s edge of life and death under such an unstable king. According to Dio Cassius, Seneca was saved from execution—for what offense, we do not know—only by his ill health:

Seneca, who was superior in wisdom to all the Romans of his day and to many others as well, came near being destroyed, though he had neither done any wrong nor had the appearance of doing so, but merely because he pleaded a case well in the senate while the emperor was present. Caligula ordered him to be put to death, but afterwards let him off because he believed the statement of one of his female associates, to the effect that Seneca had consumption in an advanced stage and would die before a great while.

It was out of the frying pan and into the fire. In a span of less than two years, Seneca would lose his father (in 39 AD at ninety-two years of age), get married (40 AD), then lose his firstborn son (40–41 AD). And then twenty days after burying his son, he would be banished from Rome by Claudius, the successor to Caligula.

What for? We are not sure. Was it blanket persecutions of philosophers? Did Seneca, in his grief, end up having an affair with Julia Livilla, sister of Agrippina? The record is murky, and, like scandals of our own time, beset with rumors and agendas and conflicting accounts. In any case, Seneca was brought up on adultery charges, and in 41 AD, at age forty-five, this grieving son and father was sent packing to the distant island of Corsica. Once again, his promising career was cut capriciously short.

Like his decade in Egypt, this would be a long time away from Rome—eight years—and although he started productively (writing Consolation to Polybius, Consolation to Helvia, and On Anger in a short span), the isolation would begin to wear on him. Soon, the man who had not long before been writing consolations to other people clearly needed some consoling himself.

He was angry, as any person would be, but rather than give in to that rage, he channeled the energy into a book on the topic, De Ira (or On Anger), which he dedicated to his brother. It’s a beautiful, touching book clearly directed at himself as much as the reader. “Don’t hang out with the ignorant,” he writes. “Only speak the truth, but only to those who can handle it.” “Walk away and laugh. . . . Expect to endure much.” This kind of self-talk dates back in Stoicism to Cleanthes, but Seneca was applying it to one of the most stressful situations imaginable—being deprived of your friends and family, an unjust conviction, the theft of valuable years of one’s life.

One of the most common themes in Seneca’s letters and essays from this period is death. For a man whose tuberculosis loomed over him from an early age—at one point driving him to consider suicide—he could not help but constantly think and write about the final act of life. “Let us prepare our minds as if we’d come to the very end of life,” he reminded himself. “Let us postpone nothing. Let us balance life’s books each day. . . . The one who puts the finishing touches on their life each day is never short of time.” While he sat in exile, he would comfort his father-in-law, a man who had just been deprived of his own job supervising Rome’s grain supply, “Believe me, it’s better to produce the balance-sheet of your own life than that of the grain market.”

Most interestingly, he quibbled with the idea that death was something that lay ahead of us in the uncertain future. “This is our big mistake,” Seneca wrote, “to think we look forward toward death. Most of death is already gone. Whatever time has passed is owned by death.” That was what he realized, that we are dying every day and no day, once dead, can be revived.

It must have been a particularly painful insight for a man who was watching years of his life tick by—for the second time—due to events outside of his control. It might not have been Stoic to despair at this, but it was certainly quite human.

In a play Seneca wrote toward the end of his life, clearly from heartfelt experience, he captured just how capricious and random fate could be:

If the breaking day sees someone proud,

The ending day sees them brought low.

No one should put too much trust in triumph,

No one should give up hope of trials improving.

Clotho mixes one with the other and stops

Fortune from resting, spinning every fate around.

No one has had so much divine favor

That they could guarantee themselves tomorrow.

God keeps our lives hurtling on,

Spinning in a whirlwind.

Fate had caused him to be born to wealth and had given him great tutors. It had also weakened his health and sent him unfairly packing twice, just as his career was taking off. Fortune had behaved, all through his life, exactly as she pleased. For him, as for us, she brought success and failure, pain and pleasure . . . usually in exactly the form he was not expecting.

Little did Seneca know in 50 AD that this was going to happen again. His trials were about to improve and his life was about to be spun into a whirlwind that history has not quite yet fully wrapped its head around.

Agrippina, the great-granddaughter of Augustus, had grand ambitions for her twelve-year-old son, Nero. Having married Claudius, Caligula’s successor, in 49 AD and convinced him to adopt Nero, one of her first moves as empress was to persuade Claudius to recall Seneca from Corsica to serve as their son’s tutor. Plotting for him to be emperor someday, she wanted access to Seneca’s political, rhetorical, and philosophical brain for Nero.

Suddenly, at fifty-three years of age, Seneca, long a subversive but marginalized figure, was elevated to the center of the Roman imperial court. A lifetime of striving and ambition finally produced the ultimate patron, and the entire Seneca family was ready to take advantage.

What did Seneca teach young Nero? Ironically, just as his father had hired Attalus to tutor Seneca in basically everything but philosophy, Agrippina wanted Seneca to teach Nero political strategy, not Stoicism. Seneca’s lessons would have revolved around law and oratory—how to argue and how to strategize. Any Stoic principles would have been snuck into his lessons like vegetables baked into a child’s muffin or sugar to cover the medicine.

Like Arius and Athenodorus with Octavian, Seneca was preparing the boy for one of the hardest jobs in the world: wearing imperial purple. In the days of the Republic, the Romans had been leery of absolute power, but now Seneca’s job was to teach someone how to have it. Just a few generations earlier, the Stoics had been ardent defenders of the Republican ideals (Cato was one of Seneca’s heroes), but by the death of Augustus most of these objections had become futile. As Emily Wilson, a translator and biographer of Seneca, writes, “Cicero hoped that he really could bring down Caesar and Mark Antony. Seneca, by contrast, had no hope that he could achieve anything by direct opposition to any of the emperors under whom he lived. His best hope was to moderate some of Nero’s worst tendencies and to maximize his own sense of autonomy.”

It makes sense, certainly, but the question remains: Could a more hopeful Seneca have had more of an impact? Or does accepting that one person is powerless to change the status quo become a self-fulfilling prophecy?

What Seneca did believe was that a Stoic was obligated to serve the country—in this case an empire that had already been through four emperors in his lifetime—as best one could, and surely he was willing to accept just about any role to get off the godforsaken island he had been stuck on.

Did he know what a Faustian bargain this would be? There were hints. Nero didn’t seem to care about his education—not like Octavian, anyway—and he seemed to want to be a musician and an actor more than he wanted to be an emperor. He was entitled and cruel, spoiled and easily distracted. These were not traits that boded well. But the alternative to Nero was returning to exile in Corsica.