Stoic Failings and What They Can Teach Us About the Art of Living

Most of the articles and books written about the history of Stoic philosophers focus on their success stories; rightfully so, as there are many of them to tell. We read about the slave made freer than his master through self-discipline, the lone senator who fought against tyranny and who, though defeated, was never conquered, and finally about the philosopher king who led his country through civil strife, foreign wars, and a deadly plague. The Stoic school, like any other philosophical school, was made up of human beings: Men and women with passions, desires, temptations, and fears that they spent their lives trying to tame. What, if anything, can we learn from the examples of Stoic failure? Principally, we can learn humility. For if even these masters of self-control could fail, so too can we. More broadly, we can recount their errors in the hope that they will allow us to see that which was obscured from these Stoics by passion and fear in their own time.

Seneca: The Embers of the Fire that Consumed Rome

Lucius Annaeus Seneca was one of the greatest Stoic philosophers of all time. Even today, 2,000 years after his death, Seneca’s works are popular among those seeking inner peace and self-control. Yet, for all his brilliance, self-mastery, and steadfast ability to endure the great hardships of disease and exile, his political legacy, and indeed his demise, would be defined by his worst student: Nero.

Seneca was an erudite youth. Born far from Rome in the distant backwater of Hispania, his future as a legal and political powerhouse was nonetheless virtually assured as he climbed the ranks of mos maiorum; the stepladder of Roman politics which all aspiring political actors had to climb. However, sometime around 20 AD Seneca would be forced to leave Rome so that his aunt could treat his illness, probably tuberculosis, in Egypt. He would live away from the hustle and bustle of the eternal city for 10 years, while his aunt treated his symptoms, and though he would eventually heal and return to Rome, his illness would harry him for the rest of his life. Sometime after his return to Rome, he would again have to leave, this time for political reasons. The new emperor of Rome, Claudius, was convinced by his wife Messalina that Seneca had committed adultery with a woman named Julia Livilla and he was exiled to the island of Corsica.

While on Corsica, we can see the seeds of Seneca’s greatest failure sprouting: his inability to stand up to vile and corrupt emperors. In the hopes of being recalled from his exile on Corsica, Seneca penned a work entitled Consolation to Polybius, which made several blandishments to the emperor aimed at receiving an official recall to the capital. It worked. In 49 AD, Agrippina, Nero’s mother, asked Claudius to recall Seneca from exile so that he might tutor her son; the emperor approved. Upon his return to Rome, Seneca spent several years tutoring the boy, hoping to make some appreciable impact on the affairs of state through him.

He failed. Seneca tried as best he could to live life on a knife’s edge, balancing his Stoicism which admonished those who sought political power above all else, and his personal-political ambition to serve in positions of immense power. He was, to be entirely fair, not hired to teach the young boy philosophy per se. Seneca was chosen by Agrippina because of his famed oratory prowess, a skill that nearly saw him executed years earlier by emperor Caligula. The ability to make grand speeches would not make Nero a good emperor. If anything, it made the petulant boy-king more effective at forcing his hedonistic will on the people of Rome.

Despite being placed in a difficult situation, Seneca failed in taming the boy, which would have disastrous consequences for Rome. Seneca’s essays written on morality and addressed to the emperor, though well thought-out and powerful in their own right, were hollow platitudes when compared to the strict, no-bullshit message Nero needed. Later Stoics, like Junius Rusticus (who appears in this article for his own failings), would not hesitate to be blunt, even when teaching emperors. This weakness in Seneca would help to breed a killer and a tyrant.

Nero was indeed a monster. He ordered the killing of his own mother, killed his political opponents (including Gaius Rubellius Plautus, a Stoic philosopher and a good man), and plunged the empire into economic ruin. While it is probably not true that Nero played the fiddle as Rome burned, as the popular legend goes, he certainly did not let the great fire of Rome go to waste as an opportunity to show off his depravity. Nero rebuilt much of the destroyed city for his personal use, erecting palaces and statues while Romans went homeless. He also raised taxes on the provinces to pay for the restitution of the city, in stark contrast to Marcus Aurelius who would sell the imperial possessions rather than levy a ruinous tax on his own people.

The tale of Seneca and Nero reminds us of a key Stoic principle: that we must always do what we know to be right, regardless of the consequences. As Marcus Aurelius says in Meditations, the most important thing in life is “just that you do the right thing. The rest doesn’t matter. Cold or warm. Tired or well-rested.” Seneca would redeem himself in the end, returning to fully embodying Stoic principles in his retirement and, like Socrates or Thrasea, dying the heroic death of a philosopher dedicated to his principles. It is important to note that none of us can know how we would react if placed in his position. Many of us who judge Seneca would almost certainly have fared much worse with a knife to our throat. However, it is important to learn one key lesson from the failings of this great man: problems only get worse if ignored, and if ignored for too long enough they will consume you whole.

Nero wasn’t in Rome when the city burned in 64 AD, but the popular myth of Nero and his fiddle captures something fundamental about the essence of the man.

Rusticus Executes a Good Man

If you ask a Stoic about Junius Rusticus, he or she will likely know him as a positive figure; a teacher and a good Stoic who served his country and taught Stoicism to perhaps the greatest Stoic who ever lived. If you ask a Christian, however, you will likely be met with a different response. To them, Rusticus represents the same unjust force that beleaguered early Christians, that threw them to the lions and crucified them. It serves as a good example of the principle that even a life lived through virtue can be altered by one single decision.

Rusticus, the grandson of a proud member of the so-called “Stoic resistance” movement, was a good man. He was a soldier, a politician, and a philosopher who served his friends, family, and country. He served first as a soldier, fighting for the glory of Rome, and through merit and skill he worked his way up to becoming a General. Under emperor Hadrian, he would serve as consul of Rome and be appointed by the same as the teacher of the future emperor: Marcus Aurelius.

After Marcus Aurelius became emperor in 161 AD upon his adopted father’s death, Rusticus was appointed to various positions of power in the government. First, he served his second term as consul of Rome, once his term as consul ended, he would serve as Urban Prefect; a position that would define his legacy. As the Stoic author Ryan Holiday puts it in his book, The Lives of the Stoics, the urban prefect was essentially the mayor of Rome. As the urban prefect, Rusticus had complete legal authority within 100 miles of Rome and was charged with the task of maintaining law and order.

The burgeoning Christian sect would prove an effective challenge to Roman authority. It is not so much that the Romans were motivated by religious zeal in their conflict with the Christians; citizens and merchants were wary of them, and politicians feared their loyalty. If, those in power thought, these Christians do not acknowledge any gods but their one “true” God, then they must deny the holy nature of the office of the emperor, and thus are traitors to the state. Years before, emperor Trajan had actually criminalized Christianity on pain of death, though Christians were not actively sought out, they would be killed for not recognizing the Roman pantheon of Gods.

This came to a head in 165 AD when a Cynic named Crescens denounced a man named Justin following a dispute. Justin was dragged before Junius Rusticus to be tried. Justin and Rusticus, under any other circumstances, would have been fast friends. In fact, Justin had been a Stoic earlier in his life, though he left the school to become a Christian. Even if Justin had not been a Stoic, he might have expected lenience and clemency from Rusticus. After all, was Justin not standing up for his principles? Was he not practicing wisdom and courage in standing up to the might of Rome for his cause? Their trial is recorded for us in the Acts of Justin, in which a conversation between the prefect Rusticus and Justin goes like this: “Rusticus the prefect said, let us, then, now come to the matter in hand, and which presses. Having come together, offer sacrifice with one accord to the gods. Justin said, No right-thinking person falls away from piety to impiety. Rusticus the prefect said, unless you obey, you shall be mercilessly punished. Justin said, through prayer we can be saved on account of our Lord Jesus Christ, even when we have been punished, because this shall become to us salvation and confidence at the more fearful and universal judgment-seat of our Lord and Savior.”

Which man sounds more Stoic in this encounter? Rusticus comes across as a despotic torturer killing a man he had the power to slap on the wrist and pass on for no reason. Junius Rusticus ordered Justin to be executed, and within the year he was beheaded. At the time, Rome’s wars and a deadly plague that would ultimately claim the emperor and 5 to 10 million souls across the empire distracted from the trial of Justin Martyr; history would remember the event better than those who lived it. The tale of Rusticus and Justin is a reminder to us to live the Stoic virtue of justice. We need to see situations from other perspectives, and we should be as lenient and charitable as we possibly can be with our fellow man. As Rusticus’ student, Marcus Aurelius would write in Meditations, “I have seen the beauty of good, and the ugliness of evil, and have recognized that the wrongdoer has a nature related to my own — not of the same blood and birth, but the same mind, and possessing a share of the divine. And so, none of them can hurt me. No one can implicate me in ugliness. Nor can I feel angry at my relative or hate him. We were born to work together like feet, hands and eyes, like the two rows of teeth, upper and lower. To obstruct each other is unnatural. To feel anger at someone, to turn your back on him: these are unnatural.”

Rusticus failed in this task and is now remembered as a monster by millions. Remember to act with justice and kindness, even, perhaps especially, when it is hard to do so.

Christians were often executed for failing to honor the Roman gods, their belief being confused with a refusal to acknowledge the supremacy of the Roman emperor.

“Life is very short and anxious for those who forget the past, neglect the present, and fear the future” — Seneca

Embracing Fate: Why an Ancient Philosophy is Resonating with Millions Today

The paradox of the modern world is that while we have never had more access to travel, food, and medicine, we also have never been more depressed and anxious. Since the 1990s, rates of depression globally have risen a staggering 49.86%, a rise that is particularly concentrated in adolescents and young adults. In order to cope with increased feelings of depression, people have turned to a variety of solutions. Many medicate. Attempting to numb the pain and sadness associated with clinical depression, 13.2% of Americans report having taken antidepressant medication at some time in the last 30 days. Others, particularly young men in the west, turn to toxic “manosphere” internet personalities and bloggers like Andrew Tate, a British-American former kickboxer turned self-help guru who is famous for his polarizing stances on various socio-political issues. While these people are investigating modern solutions to their depression and anxiety, others look to the wisdom of the past, specifically to an ancient philosophy founded more than 2,300 years ago on the painted porches of the Greek agora: Stoicism.

A Bust of the Roman Emperor and Stoic Philosopher, Marcus Aurelius

What is Stoicism and why are so many finding meaning in its teachings? The answer to that is complicated, and given the lively debates between Stoic thinkers, it also seems to depend on who you ask. To refer to something as “Stoic” in the modern world more often than not means something like “the ability to endure pain or hardship without complaint.” While this understanding does capture elements of Stoic philosophy, it also falls short of capturing the reason why so many find deep meaning in its teachings. This view of the philosophy can often alienate people who may be interested in the core message because they erroneously believe that to be a Stoic means to give up emotions and live the life of a monk; this could not be further from the truth. Stoicism, in its essence, is about control; what one can control and what one cannot. Epictetus, a Roman slave turned Stoic philosopher, opens his Enchiridion by saying “Of things, some are in our power and others not. In our power are opinion, pursuit, desire, aversion, and in one word, whatever are our own actions. Not in our power are body, property, reputation, command, and, in one word, whatever are not our own actions.” This, to many, is the central dogma that underlies much of Stoic philosophy. Something may go wrong at work, you may be dealing with interpersonal or relationship drama, or you could be dealing with a serious existential dilemma. The Stoics argue that all of that is out of your control; all that you can control is your response to those events.

Death is an orienting principle for the Stoics. Death is something that many people struggle with and is a source of much of the anxiety and depression that so afflicts modern society. A Chapman University survey found that 58.5% of people report being “afraid or very afraid” of death. Another study from the Cleveland Clinic found that between 3 and 10 percent of people have thanatophobia (from the Greek word θάνατος meaning death), or a fear of one’s own death that is so intense that it affects one’s daily life. To the Stoics, however, death is merely another fact of life over which nobody has any control. Marcus Aurelius, a Roman Emperor and perhaps the most prolific of the Stoic philosophers, famously said that “Death smiles at us all; all a man can do is smile back.” Marcus Aurelius goes a step further than even that and argues that death should be something that we reflect on constantly because it sobers us, drives us, and forces us to focus on what really matters. “You could leave life right now,” he says, “Let that determine what you do and say and think.”

This outlook is one way in which the practice of Stoicism can help us to be calmer and treat others with more kindness. When viewed through the lens of our own inevitable mortality, arguments over most daily occurrences seem like a waste of a valuable and non-renewable resource. When remembering our mortality, a concept commonly expressed by Stoics in the Latin phrase “memento mori” or “remember that you must die” in English, we also are more likely to consider what wasting our time means. Seneca, a Roman Senator and Stoic philosopher, says that dying is not something that happens in the future; you are dying now, he argues. Every moment that passes is one which can never be retrieved, and the only moment one can be certain will come to pass is the current one. Assuming one’s continued existence into the future ad infinitum is either an act of naivety or of high arrogance from the Stoic perspective. What we do with our time, too, is of paramount importance to the Stoic. “It’s not that we have a short time to live, but that we waste a lot of it,” Seneca says. Seneca also laments that while we treat those things that might harm us as though we are mortal, we treat our desires as though we are immortal. As the productivity YouTuber Ali Abdaal says, we assign our future selves superpowers, and we assume tacitly that the same factors that slow our progress in the present will no longer hinder us in the future. These assumptions and tendencies, all too common today, are shown for the shallow excuses that they really are under the sobering light of Stoic philosophy.

To illustrate the practical benefits of Stoicism in modern times, let me share my personal journey toward implementing this philosophy. In the summer of 2022, I was fat, depressed, and directionless. At 250 pounds with no sleep schedule, exercise, or concrete direction in life, mild depression set in. Going through a rough break-up with my then-girlfriend of 5 years was the icing on the self-pity cake I was eating 24/7. The rabbit hole to Stoicism was opened for me by a wonderful professor who taught an ethics course at my university. While not a Stoic himself, my professor introduced me to the work of Immanuel Kant, a philosopher loved by the Stoics who, inter alia, wrote that true freedom is the suppression of animalistic desire and that by living hedonistically (as I certainly was at this time), one is a slave to one’s animal desires. I began reading, and then implementing, the 4 Stoic virtues (justice, courage, wisdom, and temperance) as praxis into my life as best as I could manage. My initial attempts at living a virtuous life were meek, but when viewed relative to my starting point they looked massive. Of all of the Stoic virtues, temperance was the most difficult to improve upon, but I got better at it over time. I began eating a diet of 1,500 calories per day, a goal I began in October of 2022, and as of the time of writing it is one which I have not missed once. I began walking, then running, then going to the gym. Today, little more than 5 months after starting my temperance journey, I weigh 190 pounds and continue to lose around 1–3 pounds per week. While this has certainly done wonders for my health, it is important to note that not everyone will react to my specific methods of implementing temperance, and it is important that everyone do what works best for them. With only 30 pounds left until I hit my goal weight, my outlook on my physical health looks better than ever. To paraphrase Marcus Aurelius, if I do what I need to do today, I will not need to worry about the future. I look and feel better than I have in a long time with 60 pounds of weight lifted from my frame: thank you Stoicism.

Today, there are few philosopher kings like Marcus Aurelius and senators like Lucius Seneca practicing Stoic philosophy, but the school has made somewhat of a comeback in recent years thanks to the work of academic scholars and practical thinkers alike. Books published on how Stoicism can impact us today like A Guide to the Good Life by William B. Irvine and The Little Book of Stoicism by Jonas Salzgeber have sold very well and were equally well received by their readers. Ryan Holiday, an American Stoic thinker and writer, has written more than 10 books on Stoicism and runs an email list dedicated to sending one brief bit of Stoic wisdom to its subscribers every day; the list has more than 300,000 subscribers in all. Holiday’s reach in particular has had an outsized impact on regular people who are not looking to join a philosophical school per se, but who want to improve their daily lives. This is why Holiday has enjoyed more than 3 million book sales; he introduces modern westerners to what is perhaps the most powerful practical philosophy the west has ever produced in a way that is easily digestible. For more information on how Stoic practices can improve your life, any of the sources above can certainly help you in your journey toward self-mastery. Whatever you read, though, make sure to actually live the central dogma of the Stoic school; surrender your erroneous notion that you can control anything other than your own actions. Live in the moment and let your impending demise orient you and sober you up enough to enjoy the present moment, for that is all we are guaranteed.

“When you arise in the morning, think of what a precious privilege it is to be alive — to breathe, to think, to enjoy, to love.” — Marcus Aurelius