It would please Lucius Annaeus Seneca very much to know that we are still talking about him today. Unlike many of his fellow Stoics, who wrote of the worthlessness of posthumous fame, Seneca craved it, worked for it, performed for it, right down to the last moments of his life and the theatrical suicide that would rival Cato’s.

Unlike Jesus, who was born the same year as Seneca in an equally far-flung province of the Roman Empire, there was little meekness or humility in Seneca. Instead, there was ambition and talent and a will to power that not only rivaled but surpassed Cicero’s.

Contemporaries may have believed that Cicero was a better writer and speaker, but Seneca is the more widely read figure today, for good reason. No one has written more cogently and relatably about the struggles of a human being in the world—their desire for tranquility, meaning, happiness, and wisdom. The readership of the essays and letters Seneca wrote over his long life has not only eclipsed Cicero’s, but in the long run likely all the other Stoics’ combined as well.

Just as he aimed all along.

Born around 4 BC in Corduba, Spain (modern Córdoba), the son of a wealthy and learned writer known to history as Seneca the Elder, Seneca the Younger was destined for great things from birth. So were his brothers, Novatus, who became a governor, and Mela, whose son, Lucan, carried on the family’s writing tradition.

Entering the world near the end of the reign of Augustus, Seneca was the first major Stoic with no direct experience of Rome as a republic. Seneca knew only of the empire; in fact, he would live through the reigns of the first five emperors. Never did he breathe in the freedom of Roman libertas that Cato and his predecessors had all enjoyed. Instead, he spent his entire life attempting to maneuver within the turbulent court regimes of increasingly autocratic and unpredictable power.

Yet for all these changes, his childhood remained more or less identical to those of the philosophers who had come before him. His father selected Attalus the Stoic to tutor his boy, primarily for the man’s reputation for eloquence, wanting to imbue his son not just with a righteous mind but with one capable of communicating these ideas clearly and convincingly in Roman life. His son took to education with gusto—by Seneca’s own telling, as a child he cheerfully “laid siege” to the classroom and was the first to arrive and last to leave it. We know that Attalus didn’t tolerate “squatters,” the kind of students who lounge around and listen, or at best take notes so as to memorize and repeat what they heard from the lectures. Instead, it was an active process, with debating and discussion, and involved both the teacher and the student. “The same purpose should possess both master and scholar,” Attalus said of his methods, “an ambition in the one case to promote, and the other to progress.”

By progress, Attalus had more in mind than just good marks and the appearance of being articulate. His instruction was as much moral as it was academic, as he spoke at length to his promising young student about “sin, errors, and the evils of life.” He was an advocate for that core Stoic virtue of temperance, instilling in Seneca lifelong habits of moderation in diet and drink, causing him to give up oysters and mushrooms, two Roman delicacies. He poked fun at pomp and luxury as fleeting pleasures that did not contribute to lasting happiness. “You must crave nothing,” Attalus told Seneca, “if you would vie with Jupiter; for Jupiter craves nothing. . . . Learn to be content with little, and cry out with courage and with greatness of soul.”

But the most powerful lesson that Seneca learned from Attalus was on the desire to improve practically, in the real world. The purpose of studying philosophy, he learned from his beloved instructor, was to “take away with him some one good thing every day: he should return home a sounder man, or on the way to becoming sounder.”

Like countless young people since, Seneca experimented with different schools and ideas, finding value in Stoicism and the teachings of a philosopher named Sextius. He read and debated the writings of Epicurus, from a supposedly rival school.* He explored the teachings of Pythagoras and even became, for a time, a vegetarian based on Pythagorean teachings. It’s a credit to Seneca’s father, and a reminder to fathers since, that he patiently indulged this period and encouraged a range of study for his son. It can take a while for precocious young people to find themselves, and forcing them to curtail their curiosity is expedient but often costly.

What Seneca was doing was developing a range of interests and experiences that would later enable him to create his own unique practices. From Sextius, for example, he discovered the benefits of spending a few minutes in the evening before bed with a journal, and combined this with the kind of probing moral reflection that Attalus had taught him. “I avail myself of this privilege,” he would later write of his journaling practice, “and every day I plead my cause before the bar of self. When the light has been removed from sight, and my wife, long aware of my habit, has become silent, I scan the whole of my day and retrace all my deeds and words. I conceal nothing from myself, I omit nothing. For why should I shrink from any of my mistakes, when I may commune thus with myself?”

This part of Seneca, his earnest commitment to self-improvement—firm but kind (“See that you don’t do that again,” he would say to himself, “but now I forgive you”)—was beloved by his teachers and clearly encouraged. But they also knew why they had been hired, and that his father, no fan of philosophy, was paying them to train his son for an active and ambitious political career. So this moral training was balanced out by rigorous instruction in the law, in rhetoric, and in critical thinking. In Rome, a promising young lawyer could appear in court as early as age seventeen, and there is little doubt that Seneca was ready as soon as he was legally able.

Yet just a few years into this promising career, only in his early twenties, Seneca’s health nearly cut it all short. He had always struggled with a lung condition, most likely tuberculosis, but some sort of flare-up in 20 AD forced him to take an extended trip to Egypt to recover.

Life takes our plans and dashes them to pieces. As Seneca would later write, we should never underestimate fortune’s habit of behaving just as she pleases. Just because we have worked hard, just because we are showing promise and our path toward success is clear has no bearing on whether we will get what we want.

Seneca certainly wouldn’t. He would spend something like ten years in Alexandria, in convalescence. While he didn’t control that, he could decide how he would spend that time. So he spent the decade writing, reading, and building up his strength. His uncle Gaius Galerius served as prefect of Egypt, and we can imagine it was here that Seneca was given his first real education in how power operated. We can also imagine him pining for and plotting a return.

While he was away, he received news that would foreshadow the arc of his own life. Attalus had somehow run afoul of Tiberius, the emperor, who confiscated his property and banished him from Rome. Seneca’s beloved tutor would spend the rest of his years making ends meet in exile, digging ditches. To be a philosopher in imperial Rome was to walk a razor’s edge, Seneca was learning, and it was to accept that the fates were fickle and that fortune could be cruel.

Seneca’s return to Rome at thirty-five in 31 AD would only reinforce this latter lesson. On the journey home, his uncle was killed in a shipwreck. He also arrived in time to see Sejanus, once among Tiberius’s most trusted military commanders and advisors, condemned by the Senate and torn to pieces by the mob in the streets. It was a time of paranoia and violence and political turmoil. Into this maelstrom, Seneca took his first public office, serving as quaestor by virtue of his family connections.

Seneca kept his head down through Tiberius’s reign, which lasted until 37 AD and through Caligula’s, which was considerably shorter but just as violent. In his book On the Tranquility of Mind, Seneca would later tell the story of a Stoic philosopher he admired named Julius Canus who was ordered to be murdered when he fell afoul of Caligula. As Canus waited for the executioner, he played a game of chess with a friend. When the guard came to lead him away to his death, he joked, “You will testify that I was one piece ahead.”

Seneca noted not only the quip’s philosophical brilliance, but also the kind of fame it had won for its owner in this terrifying time.

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.

In 54 AD, roughly five years into Seneca’s employment at court, Agrippina had her husband, Claudius, killed by way of poisoned mushrooms. Nero was made emperor at age sixteen, and Seneca was asked to write the speeches that Nero would give to convince Rome that it wasn’t totally insane to give this dilettante child nearly godlike powers over millions of people.*

As if absolute power wasn’t corruptive enough, Nero had clearly witnessed some nasty early lessons from his mother and adoptive father. As his teacher and mentor, Seneca attempted a course correction. One of the first things he gave the new emperor was a work he composed, entitled De Clementia, which laid out a path “for the good King” and that he hoped Nero would follow. And while clemency and mercy might seem like obvious concepts to us today, at the time this was quite revolutionary advice.

Robert A. Kaster, the classics scholar, writes that there was no Greek word for clemency. Philosophers had spoken of restraint and mildness, but Seneca was talking about something more profound and new: what one does with power. Particularly, how the powerful ought to treat someone without power, because this reveals who they are. As Seneca explained, “No one will be able to imagine anything more becoming to a ruler than clemency, whatever sort of ruler he is and on whatever terms he is put in charge of others.”

It was a lesson aimed at Nero, as well as every leader who might read the essay after. The world would be a better place with more clemency in it—only a cursory look at history confirms this. The problem is getting leaders to understand it.

The dynamic between Seneca and Nero is an interesting one because it clearly evolved—or rather devolved—over time. But the essence of it is perhaps best captured in a statue of the two done by the Spanish sculptor Eduardo Barrón in 1904. Even though it depicts a scene some eighteen centuries after the fact, it manages to capture the timeless elements of the two men’s characters. Seneca, much older, sits with his legs crossed, draped in a beautiful toga but otherwise unadorned. Spread across his lap and onto the simple bench is a document he’s written. Maybe it’s a speech. Maybe it’s a law being debated by the Senate. Maybe it is in fact the text of De Clementia. His fingers point to a spot in the text. His body language is open. He is trying to instill in his young charge the seriousness of the tasks before him.

Nero, sitting across from Seneca, is nearly the opposite of his advisor in every way. He is hooded, sitting on a thronelike chair. A fine blanket rests behind him. He’s wearing jewelry. His expression is sullen. Both fists are clenched, and one rests on his temple as if he can’t bring himself to pay attention. He is looking down at the ground. His feet are tucked behind him, crossed at the ankles. He knows he should be listening, but he isn’t. He’d rather be anywhere else. Soon enough, he is thinking, I won’t have to endure these lectures. Then I’ll be able to do whatever I want.

Seneca can clearly see this body language, and yet he proceeds. He proceeded for many years, in fact. Why? Because he hoped some of it—any of it—would get through. Because he knew the stakes were high. Because he knew his job was to try to teach Nero to be good (he would literally die trying). And because he was never going to turn down a chance to be that close to power, to have that much impact.

In the end, Seneca made little progress with Nero, a man whom time would shortly reveal to be deranged and flawed. Was it always a hopeless mission? Was Seneca’s steady hand a positive influence—one that Rome would have been worse off without? We cannot know. What we know is that Seneca tried. It’s the old lesson: You can lead a horse to water, but you can’t make it drink. You control what you do and say, not whether people listen.

All a Stoic can do is show up and do their work. Seneca believed he had to, and clearly, he wanted to also. As he would later write, the difference between the Stoics and the Epicureans was that the Stoics felt that politics was a duty. “The two sects, the Epicureans and the Stoics, are at variance, as in most things,” Seneca wrote. “Epicurus says: ‘The wise man will not engage in public affairs except in an emergency.’ Zeno says: ‘He will engage in public affairs unless something prevents him.’”

Nothing was preventing Seneca—least of all his own ambitions—so he kept trying.

Sources tell us that for the first several years, Seneca was the steady hand. While he was working with Burrus, the military leader also chosen by Agrippina, Rome was, for the first time in some time according to contemporaries, well run. In 55 AD, Seneca’s brother Gallio was made consul. The following year, Seneca himself held that position.

Like the poem Seneca wrote about fate said, however, this was not to last. In fact, that seems to be the constant theme of Seneca’s life—that peace and stability are fragile and punctured, quite capriciously, by events outside his control. Nero, driven by paranoia and the cruel streak he inherited from his mother, began to eliminate his rivals, starting with his brother Britannicus, who was dispatched with poison, just like Claudius. He forced out his mother and began to make designs to kill her too—failing several times to deliver a fatal dose of poison. One account has Nero attempting to have his mother killed in an elaborate boating accident. Finally, by 59 AD, the deed was done.

That early, restrained-but-waiting Nero captured in the Barrón statue was now released. In Tacitus’s words, he deferred no more on long meditated crimes. With his power matured, and oxidized into his soul, he could do what he liked, no matter how depraved. It was a turning point noticed by Seneca, for sure. While Arius had advised Augustus to eliminate the other, “too many Caesars,” Seneca had to remind Nero that it was impossible for even the strongest king, in the end, to kill every successor. Eventually someone would come next. But Nero didn’t listen, and ultimately murdered every male in the Julio-Claudian line.

When Nero wasn’t killing, it’s not as if he was dutiful in attending to the business of the empire. He was racing chariots at a special track he liked outside Rome, with slaves dragooned into watching and clapping for him. He neglected the state so that he could perform onstage, singing and dancing like some cut-rate actor—a fact of which his attendants prevented him from knowing by, according to Suetonius, not allowing anyone “to leave the theatre even for the most urgent reasons.”

Seneca was horrified, so why didn’t he leave? How could he be a part of such an embarrassment?

One explanation is fear. His whole life he had watched emperors murder and banish with impunity. He had felt the hard hand of their injustice himself more than once. Imperial vindictiveness loomed over him. As Dio Cassius relates, “After the death of Britannicus, Seneca and Burrus no longer gave any careful attention to the public business, but were satisfied if they might manage it with moderation and still preserve their lives.” Perhaps he thought, as people think today with flawed leaders, that he could do good through Nero. Seneca had always looked for the good in people, even someone as obviously bad as Nero. “Let’s be kind to one another,” he once wrote. “We’re just wicked people living among wicked people. Only one thing can give us peace, and that’s a pact of mutual leniency.” Maybe he saw something in Nero up close, a goodness despite the flaws, that has been lost to the historical record.

Or maybe his very real fear and these blind spots were compounded by the tempting self-interest of Seneca’s position. It’s hard to get someone to see, the expression goes, what their salary depends on them not seeing.

Seneca had grown and continued to grow quite wealthy under Nero’s regime. In just a few short years, he had amassed, largely through gifts from his boss, a fortune of some three hundred million sesterces. He was certainly the richest Stoic on earth, possibly the richest ever to live. One source notes that Seneca owned some five hundred identical citrus wood tables with ivory legs just for entertaining. It’s an odd picture, thinking of a Stoic philosopher—descended from the frugal school of Cleanthes—throwing Gatsbyesque parties funded by the gifts of his murderous boss.

Although most art renders Seneca as lean and sinewy, in fact the real likeness of him survives only in the form of one statue, dating to the third century, which is actually a double bust of Seneca and Socrates. Seneca loved Socrates, marveling once that “there were thirty tyrants surrounding Socrates, and yet they could not break his spirit.” Both men don the classic philosopher’s toga. Curiously, Socrates’s wraps both shoulders, while Seneca’s right shoulder is bare—perhaps a nod to his line about how a man must realize how little he needs to be happy, it is “the superfluous things that wear our togas threadbare.” But the portrait also reveals Seneca as the older man who had clearly enjoyed his share of sumptuous banquets, and had grown quite fat in Nero’s service.

Much of our knowledge about Seneca’s opulence and fortune comes to us via a man named P. Suillius, a Roman senator who was angry at Seneca, suspecting he was behind the revival of Lex Cincia, a law with a provision that lawyers plead cases without compensation. While Suillius’s motives were quite suspect and he would later be convicted on serious criminal charges and banished from Rome, there was at least some truth to his written attacks on Seneca’s hypocrisy. Even Seneca’s response—in his essay On the Happy Life—seems to set up a standard to which he obviously falls short:

Cease, therefore, forbidding to philosophers the possession of money; no one has condemned wisdom to poverty. The philosopher shall own ample wealth, but it will have been wrested from no man, nor will it be stained with another’s blood—wealth acquired without harm to any man, without base dealing, and the outlay of it will be not less honourable than was its acquisition; it will make no man groan except the spiteful.

Cato was rich. So was Cicero. Neither of them grew rich in the service of someone as odious as Nero, however. Arius and Athenodorus were rewarded handsomely for their service to Augustus . . . but Augustus never murdered his own mother. Cato loaned much of his money to friends without interest, and did not seem interested in growing his fortune for its own sake. “What is the proper limit to wealth?” Seneca would later ask rhetorically. “It is, first, to have what is necessary, and second, to have what is enough.”

Clearly he struggled with that idea of enough. Over several years, he lent out something like forty million sesterces at high rates to Rome’s British colony. It was an aggressive financial play, and when the colony struggled under the debt, a brutal and violent rebellion broke out that eventually needed to be put down by Roman legions.

Seneca had said that a philosopher’s wealth should not be stained in blood, but it’s hard not to see the drops of red on his.

Why couldn’t he stop himself? It’s strange to say that his talent and brilliance were to blame, but it’s true—as it is for so many ambitious people who end up with controversial fame and fortune. He had been groomed since birth for greatness, expected to become a leading man of his time. He had taken every opportunity that life had given him and tried to make the best of it, he had persevered through difficulties that would have sunk anyone who wasn’t a Stoic, and he had enjoyed the good times too. He had not complained, he kept going, kept serving, kept trying to have impact and to do what he had been trained to do. What he had never done was stop and question any of it, never asked where this was leading him and whether it was worth it.

By 62 AD, it was harder to deny the compromises he was forced to make on a daily basis in Nero’s world. Perhaps there was some lost event that broke him out of his stupor. Perhaps the moral conscience he had learned from Attalus finally won out in the battle with his desire to achieve.

Finally, finally, Seneca attempted to withdraw. We know he didn’t confront Nero. That would have been too much. There is no evidence of a principled resignation, as the Stoic-inspired secretary of defense James Mattis would give to President Donald Trump in a disagreement over policy in Syria. Instead, Seneca met with the emperor and futilely attempted to convince Nero that he didn’t need him anymore, that he was old and in bad health and ready to retire. “I cannot any longer bear the burden of my wealth,” he told Nero. “I crave assistance.” He asked Nero to take possession of all his estates and his wealth. He wanted to walk away clean into retirement.

It would not be so easy.

He’d gotten his hand bloody grabbing the money, and there would be blood getting rid of it.

A few days after their meeting, Nero murdered another enemy.

In 64 AD, the Great Fire struck Rome, and, boosted by strong winds, would destroy more than two-thirds of the city. One rumor spread that Nero had started the fire himself, or at least allowed it to burn for six days so that he could rebuild the capital as he liked. His reputation as a dilettante and a psychopath were fertile seeds for these conspiracy theories, and so, moving quickly, Nero found a scapegoat: the Christians. How many he ordered to be rounded up and killed we do not know, but one of them was a brilliant philosopher from Tarsus—the same intellectual ground that spawned Chrysippus, Antipater, and Athenodorus—who had earlier escaped death thanks to Seneca’s brother during Claudius’s reign. Saul of Tarsus, whom we know today as Saint Paul, was added to Nero’s pile of bodies.*

As blood flowed and fires burned, could Seneca feel anything but guilt? Tyrannodidaskalos—tyrant teacher. That’s what they called him. It was true, wasn’t it? Hadn’t that been what he had done? Hadn’t he shaped Nero into the man he had now clearly revealed himself to be? At the very least, it was hard to argue that Seneca hadn’t lent credibility and protection to the Nero regime. Maybe it was despair that Seneca felt in those dark days—what he had tried to hold off for so long was now breaking loose.

“We’ve spent our lives serving the kind of state no decent man ought to serve,” one of the Stoics says in The Blood of the Martyrs, Naomi Mitchison’s haunting 1939 novel about the persecution of the Christians in Nero’s court. “And now we’re old enough to see what we’ve done.”

Centuries before Seneca, in China, Confucius had been a teacher and an advisor to princes. He had danced the same dance as Seneca, trying to be a philosopher within the pragmatic world of power. His balancing principle was as follows: “When the state has the Way, accept a salary; when the state is without the Way, to accept a salary is shameful.” It took Seneca much longer than Confucius to come to this conclusion. It’s inexcusable—the shame was obvious the first time his boss tried to murder his mother . . . at least it should have been to someone trained in virtue.

But that was not how Seneca saw it, not for nearly fifteen years of service with Nero. In time, he would come to echo Confucius, writing that when “the state is so rotten as to be past helping, if evil has entire dominion over it, the wise man will not labor in vain or waste his strength in unprofitable efforts.”

But he had done precisely that for far too long. Withdrawing as best he could, Seneca turned fully to his writing. In a remarkable essay titled On Leisure, published after he retired, he seems to be wrestling with his own complicated experiences. “The duty of a man is to be useful to his fellow-men,” he wrote, “if possible, to be useful to many of them; failing this, to be useful to a few; failing this, to be useful to his neighbors, and, failing them, to himself: for when he helps others, he advances the general interests of mankind.”

Only belatedly did it occur to a striver like Seneca that one can contribute to his fellow citizens in quiet ways too—for instance, by writing or simply by being a good man at home. “I am working for later generations,” he explained, “writing down some ideas that may be of assistance to them. . . . I point other men to the right path, which I have found late in life. . . . I cry out to them: ‘Avoid whatever pleases the throng: avoid the gifts of Chance!’” Seneca himself would note the irony that in communing with these future generations he was “doing more good than when I appear as counsel in court or stamp my seal upon a will or lend my assistance in the senate.”

The primary form of this service came in the shape of philosophical letters, intended not just for his friend Lucilius, to whom they were addressed, but also for publication to a wide audience. If he couldn’t impact the events of Rome directly, he figured, he could at least reach people through his pen—it could also help assure him the “immortal” fame he still craved. Succeeding on both counts, this collection, known as Moral Letters, sells many thousands of copies a year in countless languages.

Like Cicero, Seneca would spend three years (62–65 AD) completing all his letters and books, a fact for which the literary world is eternally grateful. We can imagine him liking the symmetry with such an illustrious peer, thinking even of how the theatrics of his retirement would play. It was also smart—turning to his writing was a convenient way to stay out of the fray of Nero’s increasingly volatile ways. “My days have this one goal, as do my nights,” he wrote, “this is my task and my study, to put an end to old evils. . . . Before I became old, I took care to live well; in old age I take care to die well.” Sadly, far too much of Seneca’s work before and after this period would be lost. Emily Wilson estimates that more than half of his writings did not survive, including all his political speeches and personal letters, as well as works on India and Egypt.

It was, for all the looming danger, a period of joy and creativity for him. He wrote of sitting in his rooms above a busy gymnasium, tuning out all the noise and just locking in on his philosophy. He wrote of the process of becoming, with time, a better friend to himself—an admission, perhaps, that his ambition may have been fueled by an early feeling of not being enough, of not being worth much. He said in one letter that only those who make time for philosophy are truly alive. Well, now he was actually doing that, and he was quite alive. Each day, as he wrote in his exile on Corsica, “I can argue with Socrates, doubt with Carneades, find peace with Epicurus, conquer human nature with the Stoics, and exceed it with the Cynics.”

Seneca also spoke of philosophy as a way to look in the mirror, to scrape off one’s faults. While we don’t have any evidence that he directly questioned his work for Nero in his writings—serving was part of his political code, as it would be for General Mattis in our time—we can tell that he wrestled extensively with how his life had turned out. The closest Seneca would come to addressing a figure like Nero would be in a play he wrote called Thyestes, a dark, disturbing story about two brothers battling for the kingdom of Mycenae.* It’s impossible to read this story today and not see it as a kind of dialogue between Seneca and Nero, a warning against the draws of power and the unspeakable things human beings do to each other in the pursuit of it.

The most telling line in the play states a fact that Seneca had painfully come to understand: “Crimes often return to their teacher.”

And so they had.

He writes in Thyestes, “It is a vast kingdom to be able to cope without a kingdom.” This too he was painfully experiencing. For the third time in his life Seneca had lost next to everything. He believed, as he would now write to Lucilius, that “the greatest empire is to be emperor of oneself.”

It was a realization a long time coming.

Seneca would again find that philosophy did not exist only in the ethereal world or only on the pages of his writings. Tacitus tells us that Nero’s first attempt to kill Seneca—again by poison—was spoiled by Seneca’s meager diet. It was hard to kill someone who had so turned away from their former life of opulence that he was eating mostly wild fruits and water from a burbling stream. But even this reprieve was short-lived.

In 65 AD, conspirators, including a Stoic senator named Thrasea (see “Thrasea the Fearless”) and his brother’s son, Lucan, began to plot against Nero’s life. Seneca was not directly involved, not like Cato or Brutus had been involved, but he was at least more courageous than Cicero. One rumor had it that the conspirators planned to put Seneca back in charge after Nero’s death. Is his involvement enough to redeem him? That he was finally willing to break decisively with the monster he had helped create? When the conspiracy failed, Seneca put his life on the line to try to cover for the more active participants.

This choice sealed his fate. Nero, a coward like Hitler in his last days, sent goons to demand Seneca’s suicide. There would be no clemency, despite the essay Seneca had written for his student all those years ago.

Seneca’s life had been a complex maze of contradictions, but now, staring at the end, he managed to summon a courage and a clarity that had long escaped him. He asked for something to write his will upon and was rejected. So he turned to his friends and said he could bequeath them the only thing that mattered: his life, his example. It was heartwrenching, and they broke down when he said these words.

It would seem absurd to say that Seneca had practiced for this moment, but in a way, he had. All his writing and philosophizing, as Cicero put it, had been leading up to death, and now it was here. He seized the opportunity to practice what he had so long preached. “Where,” he gently chided his weeping friends as well as the audience of history, “are your maxims of philosophy or the reparation of so many years’ study against evils to come? Who knew not Nero’s cruelty? After a mother’s and a brother’s murder, nothing remains but to add the destruction of a guardian and a tutor.”

Not long before, he had written to Lucilius that while it was true that a tyrant or a conqueror could suddenly send us off to our death, this was actually no great power. “Take my word for it,” he had said, “since the day you were born you are being led thither.” Seneca believed that if we wanted “to be calm as we await that last hour,” we must never let the fact of our mortality slip from consciousness. We were sentenced to death at birth. For Seneca, all Nero was doing was moving up the timeline. Knowing this, he could now hug his wife, Paulina, and urge her calmly not to grieve for him too much and to live on without him.

Like so many other Stoic women, she was not content to be told what to do. Instead, she decided to go with him. Slitting the arteries in their arms, the couple began to bleed out. Nero’s guards—apparently on Nero’s orders—rushed in to save Paulina, who would live on for several more years.

For Seneca, death did not come as easily as he would have hoped. His meager diet seemed to have slowed his blood flow. So next, he willingly drank a poison he had kept for precisely this moment, but not before pouring a small libation to the gods. Could he have thought in that moment back to something Attalus had said so long ago? That “evil herself drinks the largest portion of her own poison”? It was proving true for Seneca, and it would prove true for Nero soon enough as well.

The man who had written so much on death was finding, with irony, that death did not come so willingly.* Did this frustrate him? Or did he have one eye on history, knowing fate was prolonging the scene he had long meditated on? When the poison did not work, Seneca was moved to a steam bath where the heat and dense air finally finished him off. There is an entire genre of paintings of the death of Seneca, including versions done by Peter Paul Rubens and Jacques-Louis David. Invariably they seem to show Seneca as perhaps he wished to be seen, no longer fat and rich but lean and dignified again. Everyone else in the room is hysterical, but Seneca is calm—finally the perfect Stoic he could not live up to in life—as he departs from the world.

Shortly after, his body was disposed of quietly without funeral rites, per a request he had made long before, which to Tacitus was proof that like a good Stoic, “even in the height of his wealth and power he was thinking of his life’s close,” as well as his eternal legacy.

But everything else he had gained in life was lost, except for the books we now have. And within a year, Nero would take his brother too, for crimes don’t only return upon their teachers but also to the people and things they love.