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For nearly half a millennium, from Zeno to Thrasea, these philosophers had written about freedom. They had resisted tyrannical governments and they had faced the prospect of exile. Yet one cannot help but feel the privilege dripping from most of their writings.

Most of these men were rich. They were famous. They were powerful.

Cato was. Zeno had been. Posidonius and Panaetius never had to work a day in their lives.

So when each spoke about freedom, they meant it abstractly. They were not literally in chains. While Seneca would speak, with surprising relatability, about slave owners who became owned themselves by the responsibility and management of their slaves, or other Stoics would congratulate themselves for their humane treatment of their human chattel, Epictetus actually was one.

Freedom was not a metaphor for this Stoic philosopher. It was his daily battle.

Born in 55 AD in Hierapolis, Epictetus knew slavery from birth. His name, in Greek, is quite literally “acquired one.” Somehow, despite this, his tenacity, his perspective, and his sheer self-sufficiency would make Epictetus—not just in his life, not just to the emperors he influenced, but in history and for all time—the ultimate symbol of the ability of human beings to find true freedom in the darkest of circumstances.

And they were dark circumstances. Epictetus was born the son of a slave woman in what is now modern Turkey, in a region that as part of the Roman Empire was subject to its brutal laws. One of those laws, Lex Aelia Sentia, made it impossible for slaves to be freed before their thirtieth birthday. It’s a disturbing irony that Augustus, then, who passed the law and was advised by not one but two Stoic philosophers, stole three decades from Epictetus’s life. As a young boy, Epictetus was purchased by a man named Epaphroditus—a former slave himself—who went on to become Nero’s secretary and served alongside Seneca. Two emperors, with three Stoic philosophers advising them, and apparently not so much as a question about whether it was right to own a human being.*

Hardly a shining moment of courage, justice, temperance, or wisdom . . .

Epictetus had little time to ponder the fairness of his fate. He was too busy being a slave. What he could do and couldn’t do was overtly controlled. The fruits of his labor were stolen, and his body abused—Rome was not known for treating its slaves gently. He was a vessel to be used up and then discarded, like a horse that was ridden into the ground and then put down.

That he even survived into adulthood is a surprise.

Even by Roman standards, Epictetus had a cruel master. Later Christian writers portray Epictetus’s master as violent and depraved, at one point twisting Epictetus’s leg with all his might. As a punishment? As a sick pleasure? Trying to get a disobedient young kid to follow instructions? We don’t know. All we hear is that Epictetus calmly warned him about taking it too far. When the leg snapped, Epictetus made no sound and cried no tears. He only smiled, looked at his master, and said, “Didn’t I warn you?”

Why does this make us shudder? Empathy or pain? A horror at the senselessness? Or is it at the sheer self-mastery?

With Epictetus it is all this and more.

All his life, Epictetus walked with a limp. We can’t be certain whether it came from this painful incident or another, but undoubtedly he was hobbled by slavery, yet somehow unbroken all the same. “Lameness is an impediment to the leg,” he would later say, “but not to the will.”

The Stoics believed we decided how we would react to what happened to us. Epictetus, as we each hold the power to do, chose to see his disability as only a physical impairment, and in fact it was that idea of choice, we shall see, that defined the core of his philosophical beliefs.

To Epictetus, no human was the full author of what happened in life. Instead, he said, it was as if we were in a play, and if it was the playwright’s “pleasure you should act a poor man, a cripple, a governor, or a private person, see that you act it naturally. For this is your business, to act well the character assigned you; to choose it is another’s.”

And so he did.

In Nero’s court in the 60s AD, Epictetus would have seen all of the opulence, insanity, and contradictions of Rome at that time. He would later tell a story of witnessing a man come to Epaphroditus begging for help because he was down to his last million and a half sesterces (at least $3 million in today’s dollars). Was it with sarcasm or genuine bafflement that Epictetus’s rich owner replied, “Dear man, how did you keep silent, how could you possibly endure it?”

It must have also been revealing for Epictetus to watch Epaphroditus—this man who had incredible power over him—contorting himself to remain on Nero’s good side, down to flattering even the man’s cobbler in hope of winning favor. He saw aspiring candidates for the office of consul working themselves to the bone to earn the position. He saw the gifts that were expected, the spectacles that had to be put on, the chain of offices that needed to be held for years in order to get ahead. That’s freedom? he must have thought. “For the sake of these mighty and dignified offices and honors you kiss the hands of another man’s slaves,” he wrote, “and are thus the slaves of men who are not free themselves.”

The rich in Rome were no different than the rich today: Despite all their wealth, ambition turns even a powerful person into a supplicant in the hope of gaining more.

“Freedom is the prize we are working for: not being a slave to anything—not to compulsion, not to chance events,” Seneca had written. What would Epictetus have thought watching Seneca in the flesh—whose works would have been featured in the home of a well-read man like Epaphroditus—working for such a deranged boss? As a writer, Seneca may well have been the person who introduced Epictetus to Stoicism, but by his example he clearly influenced Epictetus even more: Freedom is more than a legal status. It’s a state of mind, a way of living.

Seneca, unable to walk away from Nero’s service, ultimately forced to submit to suicide, was not trapped in the same slavery as Epictetus, but he was not free all the same.

What we know is that Epictetus was horrified by what he saw in the palaces and imperial offices of Rome, and resolved to live differently. “It is better to starve to death in a calm and confident state of mind,” he would say, “than to live anxiously amidst abundance.” Seeing someone like Agrippinus—whom Epictetus likely also met—would have been a powerful counterexample, reminding him that those who marched to their own beat could be free despite the tyranny that surrounded them. “For no man is a slave who is free in his will,” Epictetus would later say, sounding much more like Agrippinus in practice than Seneca on the page.

At some point, Epictetus came formally to philosophy, though we are not sure when. By 78 AD, though, when Musonius Rufus returned from his third exile, Epictetus was there to study under him. Did he sneak off to his lectures? Did Epictetus’s master let him attend out of guilt?

We don’t know, but clearly Epictetus found a way. He would not be stopped, not even by Musonius, who was a difficult teacher. Musonius said that silence was a sign of attentive students, but Epictetus, who would have been in his twenties by the time he met Rufus, would later recount that Rufus also believed that if a student praised him, it meant they had utterly missed the challenge his lectures had aimed at them.

This was not a general challenge either. Like the best teachers, Musonius made each of his students feel like he truly understood them at their core. Musonius had said a good teacher should “seek to penetrate to the very intellect of his hearer,” and that’s what clearly happened with Epictetus.

Epictetus would describe a teaching style that was so pointed and so personal that it felt as if another student had whispered all of your weaknesses in the teacher’s ear. Once, after making an error, Epictetus tried to make an excuse. “It is not as bad as if I had set fire to the Capitol,” he said. Musonius shook his head and called him a fool. “In this case,” he said, “the thing you missed is the Capitol.” This was a teacher who demanded the absolute best from his students. To make a mistake, to use weak logic, to fail to spot your own inconsistency was to fail philosophy entirely. And to then try to minimize it? To Musonius, that was as bad as burning Rome and dancing on the ashes.