It’s time to begin our read-along of Melville’s Moby-Dick, arguably the Great American Novel. We will read it over the next 6–7 weeks, and discuss it in three parts:

• Discussion 1 (Oct. 13) — ch. 1–40

• Discussion 2 (Oct. 27) — ch. 41–86

• Discussion 3 (Nov. 10) — ch. 87–Epilogue

Along the way, we’ll send out weekly reading guides for the chapters in question. To begin, here is our first weekly discussion thread focusing on the opening chapters…

While Moby Dick is known as an infamous epic on the high seas, its first third is a narrative slow-burn, and this can put many readers off. The first forty chapters emphasize building the world, introducing crew members, and teaching us about the monomaniacal Captain Ahab.

Which first begs the question: why the intensive, slow pacing? What is Melville’s aim in these initial chapters?

We gain a better understanding through the novel’s narrator, Ishmael. He begins by sharing that suicidal ideations have sent him to seek adventure on the ocean — hoping the danger and rush of a whaling expedition can give him a meaningful existence that the malaise of the modern world cannot.

Before sailing, he hears Father Mapple preach on Jonah, the prophet who ran from God’s command and was swallowed by a sea monster. Mapple’s lesson is that man must obey the decrees of God — even if it means denying ourselves — lest we be swallowed by the Leviathan of the sea.

Shortly after this sermon, we learn of Captain Ahab, captain of the ship that Ishmael is set to board. Specifically, we hear of him through a strange man named Elijah, who warns Ishmael that his travels at sea will only lead him to doom. Ishmael, however, discards these “prophetic” warnings and sets out to sea.

Ahab himself doesn’t appear until nearly 30 chapters in, but he is perhaps the main character of this work. He’s defined by a monomaniacal quest for vengeance against the white whale named Moby Dick. Specifically, the whale ate his leg years ago, and Ahab has vowed a ceaseless quest of revenge.

We soon learn that Ahab doesn’t view Moby Dick as merely a whale, but the embodiment of evil itself. This monster represents to him a primordial chaos, akin to the Biblical Leviathan, and Ahab vows to either destroy this beast of evil, or lose his life in the process.

Thus, as Ishmael himself discovers, this whaling expedition will be anything but ordinary. Much as this quest may be a war of man against whale, it also runs the risk of becoming a rebellion against God himself...

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Obsession isn’t healthy, but it sure is interesting. And there might not be a better story of obsession in all of literature than Moby-Dick.

The plot of Herman Melville’s classic novel is so well known that it has entered into common parlance as a clichéd metaphor: if something is your “white whale,” then it is a deeply personal, but largely unattainable, goal.

In Moby-Dick, Captain Ahab’s white whale is the white whale: Moby Dick, who took Ahab’s leg long ago and still, as the story begins, is the fundamental goal of the captain’s life. The danger of such goals, and the ways we look to change our own destiny, are central themes of this, perhaps the greatest of American novels.

Today, we discuss one of the major themes of Moby-Dick, and what we ought to learn from Melville’s sprawling meditation on pride, fate, free will, meaning, and death.

However, be advised: reading this work will not leave you the same person as when you started it…

We have just voted to read Moby-Dick next!

We will read this together over the next 6–7 weeks. The first discussion is on Tuesday, October 13.

We are running a 24-hour discount to celebrate the start of this epic read-along…

25% off full book club membership, FOREVER:

Get 25% off!

Read Moby-Dick as a member of our group and you’ll get:

• Live book club discussions (biweekly) and recordings

• Weekly reading guides and regular essays to guide you

• Access to our incredible community of readers

• The entire library of articles, essays, and podcasts

The Doomed Voyage

Ishmael, the main character and narrator of the novel, is not a sailor by profession, but neither is he entirely bereft of naval experience.

In fact, Ishmael is of an odd psychological character: though a schoolmaster, he frequently feels a restlessness that demands he leave his normal, simple life and go to sea. When the novel opens, Ishmael is in precisely this state of mind: he is wandering Nantucket, Massachusetts, looking for a ship that will hire him. He meets a friend, Queequeg, who is a member of an island tribe and offers a shrunken head to Ishmael as a gift.

It turns out that Queequeg is a skilled whale harpooner, and he and Ishmael both hire themselves out to a ship called the Pequod. At first, nothing seems to be especially extraordinary about the Pequod, except that several people mention the weird reputation of the ship and its captain, Ahab. But that doesn’t dissuade Queequeg or Ishmael — after all, seamen are eccentric, and neither man is willing to give up the voyage now that they have found it. Unfortunately, they are about to discover that they should have listened to the skeptics of Nantucket…

Ahab’s Deadly Obsession

The reason that Ahab is so erratic is that he isn’t just driven by the desire to catch whales. He’s driven by the obsession to catch the whale: an albino sperm whale named Moby Dick by the sailors who have long chased him. This particular whale has evaded capture for years, leaving destroyed ships and dead sailors in his wake. Ahab, though, is determined: he will catch and kill Moby Dick, or he will die trying.

None of Ahab’s crew is especially excited about the captain’s plan. Some, like his first mate Starbuck, are positively opposed to it; Starbuck is sure that pursuing Moby Dick will eventually kill Ahab. He even considers imprisoning or killing Ahab to save the crew from his mission. But in the end, nobody is willing to stand up to their crazed captain, even though they believe his obsession to be both insane and dangerous.

One thing that becomes clear as the novel progresses is that Ahab’s focus has no limits or moral consideration. When another ship, the Rachel, asks for help looking for a boat that held the captain’s son, Ahab refuses — he won’t lose any time that might impede him from finding the whale. He instead drives his ship further and further in search of Moby Dick.

Prophecy, Fate, and Free Will

Like his story’s protagonist, Ishmael, Melville was himself raised a Calvinist with a strong sense of fate in one’s life — one of the many themes of Moby-Dick is the question of how much control we really have over our lives.

One issue that especially brings this home is that of prophecy: if a prophecy is declared, do we really have free will in that case? Or must we inevitably bring about the prophesied outcome? Such a question is one of the oldest in literature, famously encountered in the Ancient Greek tragedy Oedipus Rex.

Melville does not answer this question directly, but his story certainly wrestles with it. For Ahab is himself given a prophecy by his Parsee servant, Fedallah, predicting some strange circumstances around Ahab’s future demise: namely, Ahab will see two hearses on the sea before he dies, with the first not made by mortal hands and the second made of American wood.

Notice that the prophecy is not something explicit such as “Ahab will destroy himself in the search for Moby Dick.” Indeed, the prophecy may sound foreboding, but Ahab still has choices before him: at any point, he might abandon the mad chase, turn the Pequod around, and return home. The crucial question is not simply whether Ahab can escape his fate, but how much of that fate he is bringing upon himself should he decide to proceed. In other words, is “fate” really just the accumulated consequence of choice?

More importantly, Ahab is not simply making choices for himself. His obsession with the whale affects the lives of everyone aboard the Pequod, which have become secondary to his pursuit. Whatever awaits them at the end of the voyage, it seems that Ahab is willing to risk everything — and everyone — to reach it. Thus, in Moby-Dick, it’s clear that obsession has the potential to destroy not only us, but others, too.

Ahab’s obsession, and his refusal to consider the good of others, means that what began as a desire for revenge has morphed into something much larger: an utter refusal to accept limitation.

It is in this particular struggle that Melville’s story draws out a profound meditation upon free will, desire, and meaning itself:

• Are we free?

• What should we desire?

• How does what we desire shape how we see the world?

• Does the world have meaning beyond that which we impose upon it?

It is finally time to tackle the Great American Novel together!

Make no mistake. This deceptive story about a whale is a work of extraordinary power. It is a sprawling masterpiece that combines epic, tragedy, drama, sermon, philosophy, and theology into a profound meditation on God, fate, evil, death, free will, and the limits of human reason.

We will read it over the next 6–7 weeks, and discuss it in three parts:

• Discussion 1 (Oct. 13) — ch. 1–40

• Discussion 2 (Oct. 27) — ch. 41–86

• Discussion 3 (Nov. 10) — ch. 87–Epilogue

Along the way, we'll send out weekly reading guides for the chapters in question.

To celebrate the start of this epic read-along, we are running a 24-hour discount…

25% off full book club membership, FOREVER:

Get 25% off!

Read Moby-Dick as a member of our group and you’ll get:

• Live book discussions (biweekly) and recordings

• Weekly reading guides and regular essays to guide you

• Access to our incredible community of readers

• The entire library of articles, essays, and podcasts

We are about to vote on what to read next inside the subscriber chat. Make sure to cast your vote…

The first discussion on the next book will take place on Tuesday, October 13, at noon Eastern Time. See you all soon!

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It’s time for the second (and final) session of our introductory read of Augustine’s City of God. We meet Tuesday, September 29, at noon ET to discuss the critical Books 19 and 22.

The discussion will be streamed via Substack at this link.

For those joining our discussion group directly (available to all paid members), the Zoom link is at the bottom of this email…

Recall that Book 19 introduced us to Augustine’s summum bonum (ultimate good), namely peace. He says that both the city of God and Man have this same end — peace — but do so through vastly different means. The city of man does so through pride, or love of self, while the city of God seeks peace via love of God.

Thus in Book 22, Augustine ends by addressing what the ultimate destiny looks like:

What is the final destiny for the City of God once history ends?

Augustine is concerned with one key idea here: the resurrection of the body. Whereas Porphyry argued that only the soul is granted eternal life, apart from the body, Augustine asserts the human body itself shall be included in heaven. In other words, the human soul is not trapped in the “prison” that is the body; rather the body, along with the soul, are a composite of the fullness of human nature.

But why this emphasis on the resurrection of the body?

Well, if the summum bonum is peace, pagan philosophers could argue that, in theory, the ultimate good is a disembodied beatific vision of merely the human soul. This would put into question the goodness of not just the human body, but even the natural world itself.

Whereas Christianity says paradise will be a renewal of creation (Christ “makes all things new”), a disembodied paradise implies the natural world may be evil, or the body an immoral prison to be escaped from.

The resurrection of the body points to the fullness of human nature perfected, and defends the foundational claim of Genesis 1 that the world was created “good,” and that life as such is good.

The book ends with a meditation on the “eternal Sabbath” — the eighth day, outside of time, where the City of God’s citizens rest, love, and praise God for eternity. Augustine’s closing image is the entire city resting in unwearied contemplation of God as the totality of beatitude — the final end of all human desire.

Some key questions/ideas to ponder:

• Augustine could have ended City of God with a purely spiritual vision of the afterlife — souls contemplating God with no bodies at all. Why do you think he insists so forcefully on the flesh? What is lost theologically if resurrection is treated as merely symbolic?

• Book 22 goes to great lengths to resolve strange edge cases (aborted fetuses, cannibalized bodies, monstrous births) in regard to the human body. What does the intensity of Augustine’s focus here suggest about the importance of the human body for beatitude?

• Alongside this defense of the body is an inquiry into miracles. Why does he go to such lengths to report the various miracles of the day? What does that suggest about understanding the Christian “economy of salvation?”

• The whole work ends in a vision of Heaven and praise — perhaps a strange conclusion for a book supposedly concerned with the political (recall this book was inspired as a defense of the Christian faith in light of Rome’s fall). Does this vision of rest, in the fullness of time, play a role in the political, or is this final vision reducible to mere escapism from the chaotic realities of life?

Share your thoughts below or in the subscriber chat, along with any questions you have — we’ll incorporate them into the discussion!

Here’s the Zoom link for Tuesday:

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Episode 21 of the podcast is now live! Jeremy is joined by writer and illustrator Megha Lillywhite for a discussion on Bram Stoker’s 1897 horror classic, Dracula.

The original novel is far stranger, darker, and more profound than its modern adaptations may suggest, and the titular Count is not the brooding, romantic figure of modern vampire stories. He is something far darker that lurks at the edge of our consciousness.

Surprising to many, perhaps, is that Dracula is a deeply Christian story about the reality of evil and the struggle for the human soul. Stoker’s symbolism of blood, for example, and the contrast between vampiric immortality and Christian eternal life are fascinating to unpack.

Megha’s case for reading the book today is thus: it is thrilling, the language is rich, and it draws out the sacrifice, love, and faith required to ultimately defeat Count Dracula…

Watch the episode for free on Substack, or on YouTube if you prefer.

Enjoy!

Don’t forget to join our book club!

We’re currently reading Augustine’s City of God. The next discussion is on September 29, at noon ET.

If you missed the first session, you can watch it back here.

Subscribe now

To support our mission, please consider a paid membership. It makes a HUGE difference to the time and resources we can dedicate. You’ll get:

• Live book discussions (biweekly) and recordings

• Access to our incredible community of readers

• Regular essays to guide you through the books we’re reading

• The entire library of articles, essays, and podcasts

Thank you for joining our first session on Augustine’s City of God. As always, a fantastic discussion — if you missed it, make sure to watch the recording here.

This week’s discussion thread focuses on Book 19. Below is a breakdown of the most important ideas and questions to consider as we continue reading…

Our next discussion is on September 29, at noon ET.

Don’t miss it!

Join our reading group by taking out a paid membership below. You’ll receive all the Zoom links and will be able to take part directly:

Subscribe now

As a member, you’ll get:

• Live book club discussions (biweekly) and recordings

• Access to our incredible community of readers

• Regular essays to guide you through the books we’re reading

• The entire library of articles, essays, and podcasts

Recall that Books 11-14 emphasize the fall of angels, the fall of Man, and the origin of the two cities: the City of God and the City of Man. Allegiance to each city is predicated upon what man loves most: either God or things of the world.

Books 15-18, which are beyond the scope of our introductory read, focus on tracking the development of the two cities throughout Biblical history. Thus, as we fast forward to Book 19, Augustine looks forward to the “end of time.” He’s now concerned with asking what are the ultimate destinies of these two cities?

The primary question of Book 19 is this: “what is the highest good, and what does it mean to pursue it as a citizen of both an earthly and heavenly city at once?”

In other words, Augustine’s question is both idealistic and pragmatic — recognizing that though man is made for heavenly glory, he must navigate a fallen and chaotic world filled with suffering, vice, and corruption.

In search of the highest good, or “summum bonum,” Augustine first draws on the philosophers. He cites Varro, noting that though the ancient schools of philosophy give hundreds of possible positions on the summum bonum, all of them are flawed because they make the same fundamental error:

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Our next discussion will be at the same time in two weeks: Tuesday, September 29, at noon Eastern Time. On that call, we will be discussing Books 19 and 22.

In the meantime, the discussion will carry on inside the subscriber chat. See you in there!

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It’s time to begin our read-along of Augustine’s City of God. A truly foundational work of the Western canon, and, quite simply, one of the greatest works of Christian thought ever put to paper.

We meet tomorrow, September 15, at noon ET — we’ll be discussing Books 11, 12, and 14 primarily. You don’t strictly need to have done the reading yet, but those of you who have done some will follow the session more easily.

The first discussion will be livestreamed via Substack at this link.

For those joining our discussion group directly (available to all paid members), the Zoom link is at the bottom of this email…

This week’s discussion thread focuses on Book 14. Whereas Book 11 emphasizes the cosmic birth of evil and the fall of the Angels, Book 14 now turns our attention to the Fall of Man.

Saint Augustine begins by clearing up a common misconception. Scripture speaks of the “desires of flesh,” at war with the “desires of spirit.” Many heretics of the day interpreted this in a Gnostic sense, claiming that the soul is in opposition to the body and material world.

Augustine, and Christianity more broadly, rejects this. He insists that nature is created Good, but corrupted by evil. Thus, the proper love of life does not include denying the body, the physical world, or our natural pleasures, but ordering them toward their proper ends, toward love.

Augustine says the correct understanding of “living according to the flesh,” then, refers to man’s rejection of God in favor of self. In other words, man’s destiny in life is determined by humility or pride — will he, to paraphrase John Milton, “reign in Hell, or serve in Heaven?”

This simple “crossroads” defines not just man’s destiny, but the underlying narrative of the cosmos and salvation history as such.

For Augustine, salvation history is quite literally a tale of two cities, ruled by two loves: either love of God or love of self. The man who dares to love God first owes allegiance to the heavenly city, and acts in cooperation with Providence. He becomes a conduit to help “make all things new.” The man who loves himself, however, dooms his destiny to destruction, no matter how clever, powerful, or well-intentioned he may be.

To put it simply, humans are creatures of worship by nature. That which we love most is what we worship, and that which we worship determines what we become.

Some key questions/ideas to ponder:

• Augustine’s account of spiritual war is not body vs. soul, but pride vs. obedience. Why does he consider it so important to emphatically reject the Platonic/Manichean notion of “spiritual world = good, physical world = evil?”

• “Two loves have made two cities” is one of the most quoted lines in the whole work. Ponder the significance of one’s loves as the arbiter of one’s destiny. Does this cohere with our modern conception of politics? Is the truest form of change to be found in the spirit, as Augustine says, rather than in the reform of institutions, doctrines, and legal systems? Can these two lines of thinking coexist? Or must they be in opposition?

Share your thoughts below or in the subscriber chat, along with any questions you have.

Here is the Zoom link for tomorrow:

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The world ended in 410.

Not the entire world. But the world that was known for almost a millennium, a world in which the empire of Rome governed, defended, ruled, and civilized Northern European, African, Middle Eastern, and Mediterranean peoples from Egypt to England, ended in 410. In that year, after many years of visible decline in and around the city of Rome itself, the Visigothic barbarians invaded and sacked the eternal city.

It’s difficult to imagine the psychological and political impact this attack had on Roman citizens. If there had been one constant in Western Civilization for the past near-millennium, it was the invulnerability and dominance of Rome over the rest of the world. Roman citizens were safe in the Roman empire, and they could live confident in their place in the greatest civilization in the world. Rome produced the best art, literature, philosophy, and, perhaps most importantly, soldiers in the world. What wasn’t to like?

Now that was shattered, left in a heap of destroyed buildings and dead corpses. And many Romans, especially the Roman aristocrats, knew who was to blame: Christianity.

Which is why the sack of Rome in 410 prompted the writing of perhaps the greatest work of theology between the Bible itself and St. Thomas Aquinas’s Summa Theologiae. It was written by St. Augustine of Hippo, and it would come to define Augustine’s reputation as a thinker. It was called The City of God.

Angering the Gods?

For centuries, the very core of Roman culture had been its religious system. The Roman religion had inspired the citizens of the empire to incredible acts of artistry, politics, and combat. Some of those acts can still be seen today, over 2000 years later.

As many know, that all changed when the Roman emperor Constantine issued the Edict of Milan in 313, officially establishing tolerance of Christianity in the Roman empire. Later, Christianity was made the official state religion, and the traditional Roman religion became the practice of only a few. Those who held on, however, warned that a reckoning was coming soon. The Roman gods had, for centuries, defended and propagated the Roman Empire across the globe. Now that the empire had abandoned them, those same gods were sure to abandon Rome. And what would become of the empire then?

One hundred years later, the Roman prophets seemed to be vindicated: Rome did fall. The borders of the empire rapidly receded, and barbarians began controlling vast swathes of what was, at one time, Roman land, including Rome itself. The Roman gods had indeed seen their vengeance wrought on those who had abandoned them.

The World’s Greatest Theologian

It was here that Christians appealed to the world’s greatest theologian, a man who still inspires and teaches millions: St. Augustine, Bishop of Hippo.

Augustine was already well-known as a prolific writer and erudite scholar; indeed, his true magnum opus, a work known as The Confessions, had already been published by this time. But whereas The Confessions was largely a work of autobiography with a healthy serving of philosophy mixed in, The City of God is a work of theology through and through.

Augustine began it in response to the many Romans who were blaming Christianity for the failure of the Roman Empire. But Augustine did not stop there. Instead, he took on a much more expansive goal: he sought to give a full account of history from the perspective of man’s relationship with God. While this would help to refute the Roman pagans, it would also achieve something much greater: it would help its readers to see all of history as a conflict between those who are following God, and those who are not. And his account would fundamentally impact Christendom’s view of the world for centuries after…

The Two Cities

The City of God is not actually about one literal city, Rome, Hippo, or otherwise. Instead, the two “cities” are the two categories of people: those who sought to do the will of God, and those who sought to pursue their own will.

It is helpful, here, to remember that the people of Augustine’s day thought of a “city” as a much more cohesive whole than we do today. Whereas we now think of cities as, basically, larger, more centralized groups of people within a country, the ancients viewed cities as the fundamental political reality. The “city of God” and “city of man” would be titled something more like “the army of God” or “the nation of God” today.

Here is how Augustine scholar Etienne Gilson describes the two cities:

The two cities which he describes are, as we have seen, mystical, that is, supernatural, in their very essence. The one is the City of truth, of the good, of order, of peace; it is, indeed, a true society. The other, since it is defined as the denial of the former, is the city of terror, of evil, of disorder and confusion; it is, in fact, a mockery of a society worthy of a name.

In other words, every person has a choice: he can become a citizen of the City of God and look to serve his creator, or he can join the city of man, and seek to serve only his own personal goals.

In Augustine’s mind (as well as in his book), all of history is the presentation of the same question that is presented to each and every human person: whom will you serve? God or himself?

In The City of God, Augustine argues that we must serve God. This choice, while it presented itself starkly to the Romans grappling with the fall of Rome, still presents itself to us today, and it is why this work still matters 1600 years after it was written. Indeed, for anybody living through difficult or uncertain times, through a decline of their city or their state, The City of God reminds us that there are things higher and more permanent than Rome:

Lay hold now on the celestial country, which is easily won, and in which you will reign truly and for ever. For there shalt thou find no vestal fire, no Capitoline stone, but the one true God… Incomparably more glorious than Rome is that heavenly city in which for victory you have truth; for dignity, holiness; for peace, felicity; for life, eternity.

Read It With Us…

Our read-along of The City of God begins this week! Please join us — it’s going to be an incredible journey.

Since it would take many months to break down all 22 books in sufficient detail, the live discussions will instead focus on the heart of the work:

Discussion 1 (September 15):

• Book 11 – creation, the angelic fall, and the origin of the two cities

• Book 12 – evil as privation, and how a good creature can turn away from God

• Book 14 – the two loves that found and distinguish the two cities

Discussion 2 (September 29):

• Book 19 – peace, justice, and the proper ends of human community

• Book 22 – resurrection, the beatific end, and the eternal rest of the City of God

Along the way, we’ll send out weekly reading guides for the books in question. Note: we are personally reading this version, the Bettenson translation (Penguin Classics).

Our next read-along has been decided, and it’s a significant one...

Saint Augustine’s City of God.

This is a foundational work of the Western canon. Quite possibly the greatest work of Christian thought. It will be one of our most rewarding — and challenging — reads thus far. If you’ve been on the fence about joining our group, now is the time…

The City of God is a long, complex philosophical work. It would take many months to break down all 22 books in sufficient detail, so instead, we’re going to make this read-along an “intro to the City of God.” The live discussions will thus focus on the heart of the work:

Discussion 1 (September 15):

• Book 11 – creation, the angelic fall, and the origin of the two cities

• Book 12 – evil as privation, and how a good creature can turn away from God

• Book 14 – the two loves that found and distinguish the two cities

Discussion 2 (September 29):

• Book 19 – peace, justice, and the proper ends of human community

• Book 22 – resurrection, the beatific end, and the eternal rest of the City of God

Along the way, we’ll send out weekly reading guides for the books in question. Note: we are personally reading this version, the Bettenson translation (Penguin Classics).

To begin, then, below is some key context to the work, and our first weekly discussion thread focusing on Book 11…

A Tale of Two Cities

In the early 5th century, the civilized world was falling into chaos. Rome itself was violently sacked in 410 AD, and its provinces faced being plunged into darkness. An order that had once seemed impenetrable was no more: if even the Eternal City could fall, then surely nowhere was safe.

At the time, pagan critics blamed Christianity for the catastrophe, claiming Rome’s fall was judgment for betraying its pagan past. It was in this context that Augustine of Hippo, a theologian and philosopher living in the Roman province of Numidia, was inspired to give a defense of the Christian faith. In The City of God, he rebukes and dismantles pagan religion and philosophy — yet in totality, it became far more ambitious a work than a mere pagan hit piece.

Ultimately, the work became a 1,000-page masterpiece offering a deep inquiry into human nature, history, politics, and civilization itself. And though it promises to give a totalizing account of mankind’s story, its genius can be boiled down to a single idea:

All of human history can be understood as a tale of two cities; namely, the City of God, and the City of Man.

Through this framework, Augustine seeks to provide an answer for anyone living through a difficult or uncertain age. But rather than a manual for saving a collapsing empire, or any political body, The City of God asks a deeper question:

What ultimately makes a society flourish?

The answer is not what you’d expect — in the end, a civilization’s true destiny is determined by what it loves...

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Thank you all for being part of our read-along of The Brothers Karamazov! What a transformative six weeks that was…

The formal read-along has come to an end, but the discussion need not finish! All the discussion threads are still open inside the community chat (see links below).

You can also find all our content related to Brothers K. (book club recordings, essays, podcasts, etc.) in one place, right here.

The discussion continues…

Books 1–4

Book 5

Book 6

Book 10

Book 11

We are about to vote on what to read next inside the subscriber chat.

The first discussion on the next book will take place on Tuesday, September 15, at noon Eastern Time — see you all soon!

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Episode 20 of the podcast is now live! Jeremy is joined by author and podcaster Auron MacIntyre for a discussion on Niccolò Machiavelli’s The Prince.

They begin with the central question: is The Prince a handbook for tyranny, or is it simply an unflinching description of how politics actually works?

And more fundamentally, perhaps: can a “good” person ever be a successful ruler?

To answer these questions, the discussion dives into what Machiavelli really meant by virtù. It examines his ideas of power and political necessity, as well as his famous distinction between being feared and being loved.

Centuries on from being written, The Prince remains a hotly debated and highly misunderstood text. What is clear, though, is that this little book remains both indispensable and unsettling — for it strips the veil from power so we can see it clearly for what it is…

Watch the episode for free on Substack, or on YouTube if you prefer.

Enjoy!

Don’t forget to join our book club!

We’re currently reading The Brothers Karamazov. The next discussion is TODAY, September 1, noon ET — join us!

Watch back the previous discussions here if you missed them.

Subscribe now

To support our mission, please consider a paid membership. It makes a HUGE difference to the time and resources we can dedicate. You’ll get:

• Live book discussions (biweekly) and recordings

• Access to our incredible community of readers

• Regular essays to guide you through the books we’re reading

• The entire library of articles, essays, and podcasts

Our read-along of The Brothers Karamazov is coming to an end. We meet tomorrow, September 1, at noon Eastern Time, to discuss Books 10–Conclusion.

Tomorrow’s session will be live streamed via Substack at this link.

For those joining our discussion group directly (available to all paid members), the Zoom link is at the bottom of this email…

Today’s thread will focus on Book 11, which finally returns us to Ivan, and continues the psychological unraveling that’s begun to unfold since the murder.

In this book, Ivan makes various visits to Smerdyakov. Recall that Smerdyakov is a vile nihilist, and though Ivan despises him, Smerdyakov considers him a good friend. This is because Smerdyakov understands the fullness of Ivan’s philosophy — that “without God, anything is permitted” — and he takes this proposition seriously.

Over their dialogues in this text, Smerdyakov slowly reveals that he has knowledge about Fyodor’s murder. Eventually, he confesses outright that he himself was the murderer, directly inspired by Ivan’s philosophy.

At this news Ivan is fraught with guilt, disgust, and illness, as he sees his culpability in his father’s murder.

This illness leads to one of the book’s most famous and striking scenes:

Ivan has a hallucinatory conversation with the devil, who appears to him as a tired, shabby, banal bureaucrat. It’s an absurd portrait, almost a direct inversion of the classic “grand seducer” image we associate with the devil, but this doesn’t make the devil’s attacks any less powerful. He affirms Ivan’s greatest fears — that the devil is real, Ivan is guilty, and that Ivan himself is too weak a man to have faith in grace, God, and love for his neighbor. Shortly after, Ivan passes out into a delirium of brain fever, losing his grasp over his faculties.

Some questions/ideas to ponder:

• Smerdyakov insists that Ivan is the real murderer, and that Smerdyakov himself was just the instrument who carried out his beliefs. Consider whether this is true, and whether or not Ivan shares in the moral culpability of Fyodor’s murder. Also consider how this relates to Father Zosima’s assertion that everyone is guilty of all before all.

• Recall also Ivan’s thesis in Book 5 — that without God “everything is permitted.” How well does this theory hold up in practice, in light of Book 11? Is Ivan correct? Does he really believe everything is permitted? How does his illness help or hurt the validity of his philosophy?

• Again, Dostoevsky’s devil is deliberately portrayed as a banal, whining, uninspired bureaucrat. Why does Dostoevsky choose to render evil in such a deflated and unglamorous manner? Why is the devil — the root of all evil — considerably weaker and less impressive than Ivan himself? What might this suggest about the nature of true evil?

Share your thoughts below or in the subscriber chat, along with any questions you have — we’ll incorporate them into the discussion!

Here’s the Zoom link for tomorrow…

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We have already covered how Dostoevsky demonstrated the self-destruction of vice in Crime and Punishment. In the book, Raskolnikov’s pride and violence lead not only to his conviction for murder, but to the erosion of his whole character.

But you’d be wrong if you thought that Dostoevsky was only concerned with action. In fact, he was just as concerned with the ways that ideas, and especially false ideas, can lead to a person’s destruction.

Those ideas are given such a demonstration in Dostoevsky’s last and greatest novel, The Brothers Karamazov.

This demonstration offers a picture of evil that is perhaps even more striking than in Crime and Punishment: the gradual, but total, collapse of Ivan Karamazov…

Don’t forget to join our book club!

We’re currently reading The Brothers Karamazov. The next discussion is on Tuesday, September 1, noon ET — join us!

Watch back the previous discussions here if you missed them.

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The Man of Great Promise

When Ivan Karamazov is first introduced, he is a flawed but relatively normal and relatable person. As a Karamazov, Ivan is naturally compared to his profligate father and blustering brother, and comes out looking incredibly well in the comparison. In fact, Ivan seems to be a positively sympathetic character: he’s no Alyosha, but he seems to have his head on straight, at least.

In fact, Ivan has his head more than on straight. He’s a philosopher and a truly brilliant writer — so much so that he writes essays on theology that confound even the learned monks and theologians of the local monastery.

There’s just one problem: Ivan is deeply nihilistic, too. And while this isn’t exactly grounds for major concern in the beginning — at least he’s not his father or brother — the consequences of the novel’s central murder are arguably worst of all for Ivan because of this…

Ivan’s Most Dangerous Idea

Early in the novel, Ivan argues with his pious brother, Alyosha, about God’s existence. Specifically, Ivan is convinced that, with the world being as evil as it is and filled with innocent suffering, there is simply no way that God could possibly exist. Or at least, God must have no right to have any person believe in him.

Ivan first points out that the world we live in is filled with grotesque evil; human beings are capable of truly horrific things, and Ivan has made a hobby of collecting stories of these atrocities, especially those committed against women and children.

Ivan’s response to these actions is to conclude that there simply cannot be a greater purpose to the world in which we live; if there were, the sheer amount of evil we see could simply not exist. Instead, the only thing that we can really count on is that our existence is utterly absurd. Ivan explains it to Alyosha thus:

“Let me tell you, novice, that the absurd is only too necessary on earth. The world stands on absurdities, and perhaps nothing would have come to pass in it without them. We know what we know!

…I don’t want to understand anything now. I want to stick to the fact. I made up my mind long ago not to understand. If I try to understand anything, I shall be false to the fact, and I have determined to stick to the fact.

…All I know is that there is suffering and that there are none guilty…I know that, and I can’t consent to live by it! What comfort is it to me that there are none guilty and that cause follows effect simply and directly, and that I know it?⁠—I must have justice, or I will destroy myself.”

—Book V, Chapter 4 (“Rebellion”)

The pain Ivan feels is a genuine “thirst for justice.” He cannot see any way that a good God would allow the things that God does in this world, and so he cannot believe:

“I want to see with my own eyes the hind lie down with the lion and the victim rise up and embrace his murderer. I want to be there when everyone suddenly understands what it has all been for. All the religions of the world are built on this longing, and I am a believer. But then there are the children, and what am I to do about them? That’s a question I can’t answer.”

Here, almost anybody can understand where Ivan is coming from, and he communicates the problem of suffering just about as well as anyone else you’ve read. The sheer amount of pain and evil in the world is hard to understand. It is deeply challenging to those of faith. The problem, of course, is that the alternative is no better.

Ivan realizes that, if there is indeed no universal purpose, and everything is absurd, then there is surely no good reason to reject any action on fundamentally moral grounds. Instead, Ivan accepts total moral anti-realism: If God does not exist, anything must be permitted.

It is this principle that Dostoevsky finds most dangerous, and as we shall see, it makes Ivan’s statement that he would “destroy himself” more prophetic than he realizes…

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Thanks again to all who joined our amazing session on The Brothers Karamazov last week. If you missed it, we highly recommend you watch the recording here.

This week’s discussion thread focuses on Book X, which takes a strange break away from the Karamazov family and the murder mystery.

Below is a breakdown of the most important ideas and questions to carry in your mind as we continue reading…

We next meet on September 1, at noon ET. We’ll be covering Books 10-12 + Epilogue. You can catch up on all previous discussions here.

Join our inner circle group by taking out a paid membership here. You’ll receive all the Zoom links and will be able to take part directly:

Subscribe now

As a member, you’ll get:

• Live book discussions (biweekly) and recordings

• Access to our incredible community of readers

• Regular essays to guide you through the books we’re reading

• The entire library of articles, essays, and podcasts

In Book X, we are reintroduced into the world of the schoolboys from earlier in the text. Primarily, we follow Kolya Krasotkin.

Kolya is a thirteen-year-old who believes himself to be wise beyond his years. He claims to be well-read yet toys with socialist talking points he doesn’t fully understand. His friendships are enigmatic, as he treats the other boys with a mixture of condescension and affection. Alyosha deduces the boy is insecure and terrified of looking foolish.

Most importantly, Kolya is the sole friend of the now sickly and dying Ilyusha — the bullied schoolboy who bit Alyosha’s finger earlier. Despite Ilyusha’s pride, he idolizes Kolya, yearning for his friendship as a solace in his last days.

Importantly, Kolya devises the perfect gift to surprise Ilyusha with:

He plans to surprise him with Zhuchka, the dog Ilyusha formerly feared he had killed. Alyosha, watching all this transpire, sees in Kolya the raw material of love, kindness, and humility that can counteract the boy’s growing intellectual pride. As such, Kolya can be reconciled as a youth whose demeanor is a mixture of Ivan’s and Alyosha’s, while Alyosha hopes to draw him closer to true humility.

Below are the key questions and ideas for us to ponder ahead of the next discussion:

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Systems of education today are dramatically different to those of past societies. We often forget just how much has changed.

This is not merely to say that the subject matter has changed along with advances in human knowledge. Today, the philosophy of public education has been reduced almost entirely to careerism — you must attend school in order to get a job and make money. It is difficult to overstate how devastating this philosophy is, and what has been lost with it.

Ancient and medieval societies had a radically different idea of what education should be. It wasn’t about readiness for work, but cultivation of the moral and intellectual virtues that free the mind.

So what does that education look like?

Traditionally, a liberal arts education was built upon seven disciplines. But rather than a set of disconnected “subjects,” each discipline built on the other, forming a systematic track to shape you into a harmonious union with Truth, Beauty, and Goodness.

Once you understand these disciplines and master them, your education will shape your mind and soul to live well — and to discover your life’s destiny…

Don’t forget to join our book club!

We are currently reading Dostoevsky’s The Brothers Karamazov! The next discussion is on Tuesday, September 1, at noon ET.

Watch the recordings of previous sessions here.

Subscribe now

To support our mission, please consider a paid subscription. It makes a HUGE difference to the time and resources we can dedicate. You’ll get:

• Live book discussions (biweekly) and recordings

• Access to our incredible community of readers

• Regular essays to guide you through the books we’re reading

• The entire library of articles, essays, and podcasts

The Trivium — Learn to Think and Speak

These artes liberales, or the “tools of freedom,” were “liberal” because they were the kind of things studied by free men, as opposed to strictly practical education (e.g., agriculture or toolmaking) for servī, "slaves." Free men were able to seek knowledge that wasn't for a pre-defined purpose, but instead to transform them personally. Music, for example, was studied not for its practical uses, but for its effects in purifying the soul.

From the 12th century, a standard university course was built on the trivium and the quadrivium. The first three disciplines, the trivium, consisted of grammar, logic, and rhetoric. The trivium has one underlying purpose:

To train the mind to think and speak properly.

1. Grammar

It begins with grammar. Traditionally, grammar was not a bland set of rules, rather, grammar explained how language itself carries meaning and how ideas are built and structured. It trains the mind to notice patterns, distinctions, and nuances in communication.

For instance, consider the sentences:

“Let’s eat, Grandma.”
“Let’s eat Grandma.”

One comma changes the sentence’s entire meaning.

So, it’s not just about arbitrary rules to write well — grammar trains your mind to think systematically and use language to express meaning with precision. Naturally, this skill leads into the next discipline.

2. Logic

Logic is the discipline of reasoning itself. Grammar gives you the tools to form sentences, but logic teaches you how to analyze those sentences up against truth. You learn the process of composing sound arguments and discerning fallacious ones, and the goal is to rationally deduce sound knowledge that can be trusted.

Consider, for instance, this famous syllogism:

• Premise 1: All humans are mortal.

• Premise 2: Socrates is a human.

• Conclusion: Therefore, Socrates is mortal.

Ultimately, logic is the bridge between knowing words and knowing ideas, to discover truth. At this point, you’ve learned to think and speak, and are now ready for the third discipline.

3. Rhetoric

Rhetoric is the art of persuasion and expression. It teaches you how to express your ideas effectively.

Speaking truthfully alone isn’t enough to win a debate or garner support for your cause. There is an art to persuasion that must be mastered if you want to move the minds and souls of your loved ones to accept Truth.

This is the discipline that changed destinies in the ancient world. Greco-Roman antiquity saw the rise and fall of civilizations, spurred on largely by the rhetorical excellence of magnanimous statesmen.

This wisdom still rings true to this day — if you want to make a mark in this world, you must learn to communicate effectively. You must learn the art of rhetoric.

With this third discipline in line, you’re now prepared for advanced education in the liberal arts.

The Quadrivium — Learn the Patterns of Reality

The quadrivium is studied after the trivium. It consists of Arithmetic, Geometry, Music, and Astronomy. Unlike the trivium, which is about how we think and communicate, the quadrivium is about how the universe itself is ordered.

It teaches your mind to see patterns, relationships, and harmony everywhere. Most important, it trains you to see your relationship to that reality (more on this later)…

4. Arithmetic

First, arithmetic is the study of numbers and quantity (addition, subtraction, fractions, etc.) But why should we understand mathematics in the first place (beyond the practical utilities in the workplace)?

Well, a deeply mathematical mindset helps you to understand abstract thinking, reasoning, and basic pattern recognition. This pattern recognition acts as a ladder to greater heights of the intellect.

5. Geometry

Geometry comes next. Building on our arithmetic skills, geometry investigates shapes, space, and the relationships between points, lines, and surfaces. This teaches you logical deduction and visual reasoning, or understanding how parts relate to a whole.

For example, Pythagoras’ theorem (a squared + b squared = c squared) isn’t just an abstract formula, but a means of discerning order in space.

Through geometry, you understand that the material world is ordered, with concrete manifestations of harmony underlying these mathematical equations. You now can perceive structure in everything — architecture, ethics, business systems — because order in space mirrors order in thought and the cosmos.

Soon enough, you start to see an underlying beauty in these patterns. You’re now ready for the next discipline.

6. Music

Music is the next discipline of the quadrivium. It’s not just about playing instruments and making beautiful sounds, but ultimately understanding proportion, harmony, and mathematical relationships in sound itself.

Consider the classical idea of the musical scale: the octave, fifth, and fourth are all ratios (2:1, 3:2, 4:3). A discernment of these patterns helps you understand not just pattern recognition of reality, but also how beauty is interwoven into the fabric of existence itself.

Music teaches that the universe has rhythm and proportion, and that certain patterns create harmony, others discord. Implicitly, you recognize which patterns are harmonious in reality, and which patterns cause discord.

This goes beyond music, and can inform your moral life. You recognize that life is about discerning a harmonious relationship of reality via pattern recognition of truths that underlie its substructure. In other words, do good so that you can be in harmony with the goodness underlying the cosmos.

7. Astronomy

Speaking of which, the cosmos is the final discipline. Astronomy studies the movements and patterns of celestial bodies. Discerning the patterns of the cosmos reinforces the idea that reality is governed by a law and order that points to a higher mode of being, and perhaps a greater transcendental reality.

The study of the heavens cultivates awe, curiosity, and a sense of proportion. You begin to recognize that education itself is an embodied experience.

In other words, you have a soul that partakes in a relationship with the cosmos. The same beauty in space rings true in your soul. You share an intimate relationship with a greater whole, and discover that there is a unified beauty hidden behind all of Being itself.

And finally, having completed the seven liberal arts, you’re ready for the next level of education — one that reveals the unity and beauty behind all of Being…

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Our third and final session on The Brothers Karamazov will be at the same time in two weeks: Tuesday, September 1, at noon Eastern Time. On that call, we will be discussing Books 10–12, plus the epilogue.

In the meantime, the discussion will carry on inside the subscriber chat. See you in there!

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Our read-along of The Brothers Karamazov continues. We meet this Tuesday, August 18, at noon Eastern Time. We’ll be discussing Books 5–9.

If you missed the first session, don’t worry — you can catch up on the recording here.

Tuesday’s session will be live streamed via Substack at this link.

For those joining our discussion group directly (available to all paid members), the Zoom link is at the bottom of this email…

You can join our inner circle group by taking out a paid membership here:

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This is proving to be one of our most rewarding read-alongs yet. If you’ve been on the fence about joining our inner circle, now is a really great time to join us!

Today’s thread will focus on Book 6, which gives credence to Father Zosima’s teachings and backstory.

We find out that the wise and noble elder had a conflicted past. His brother and parents died when he was young, and though he took to Christianity in childhood, he grew up to become a morally reprehensible officer in the army. Eventually, his behavior catches up to him after challenging a gentleman to a duel over a woman.

The night before, he grows tormented and irritable and strikes his servant. Then, after a sleepless night a profound spiritual experience comes over him. He feels remorse for striking his servant, offending the gentleman, and his years of debauchery. After making apologies to his servant, he arrives at the duel and closes his eyes, preparing for death.

However, the gentleman misses his shot, and Zosima, overjoyed, throws his pistol into a tree. He begs forgiveness of the gentleman, and after much scandal, the town falls in love with his spiritual fervor as Zosima announces he’s joining the monastery.

Some question/ideas to ponder:

• Dostoevsky’s most moral characters are rarely saints without a past. It’s often the case that his “saints” reach a spiritual maturity after repentance from great evil. Why might this be the case? And why is Zosima’s backstory so enlightening to the nature of his gentle character?

• Consider the profound spiritual experience that leads to Zosima’s repentance. It almost defies explanation. Why is this the case, and what happened to Zosima specifically? Do you consider this lazy writing, or might it be the case that a true change of heart transcends neat explanation?

• Perhaps the key idea in all of Zosima’s teaching is this: we are all guilty before all. Every one of us is guilty and collectively responsible for the evils of the world, and until you know this, you will limit your self-knowledge, happiness, and ability to love your fellow man. Why does he argue this? Do you agree with him? Why or why not?

Share your thoughts below or in the subscriber chat, along with any questions you have — we’ll incorporate them into the discussion!

Here is the Zoom link for Tuesday…

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For something slightly different, Sean hosted Liza Libes (of Pens and Poison fame) for an impromptu discussion on The Brothers Karamazov, focusing especially on Book V (“Pro and Contra”).

Sean and Liza examine the pivotal dialogue between Alyosha and Ivan, in particular:

• Rebellion: Ivan’s rejection of a world (and a God) that permits the suffering of innocent children for the sake of some eventual harmony — and his famous line about “returning the ticket.”

• The Grand Inquisitor: Ivan’s poem in which Christ returns to Earth during the Spanish Inquisition and is arrested. The Inquisitor argues that free will is an unbearable burden for most people; the Church has therefore chosen security and authority over freedom…

Enjoy!

Don’t forget to join our book club!

We just started reading Dostoevsky’s The Brothers Karamazov! The next discussion is on Tuesday, August 18, at noon ET.

Watch the recording of the first session (covering Books 1–4) here.

Subscribe now

To support our mission, please consider a paid subscription. It makes a HUGE difference to the time and resources we can dedicate. You’ll get:

• Live book discussions (biweekly) and recordings

• Access to our incredible community of readers

• Regular essays to guide you through the books we’re reading

• The entire library of articles, essays, and podcasts