Crying for a broken Tolstoy

Spiritual transformation can be hazardous to writing

I was reading Anna Karenina last night and I cried. The book didn't make me cry. I'll tell you why I cried if you read till the end. But let's talk about Anna Karenina first.

Anna Karenina is a difficult book. It’s 800 pages long and it’s about Russia in the 19th century. I’m 350 pages through and so far there are two main stories. First, there’s the story of Anna Karenina who’s stuck in a loveless marriage and taking risks that go against social norms. Then there’s the story of Levin, a nobleman who is deeply confused about his privilege and relationship with his tenant farmers, and wants to find a better system that works for them all.

The book is dense with obscure words and references. Every two minutes I need to take a picture of the page I’m reading and ask ChatGPT what some character meant, or ask it to translate the French phrase that some guy used. On some days I make good progress with the book. On others, it's hard to complete even 10 to 15 pages in an hour. Yesterday was one of those days.

In the portion I was reading, (minor spoilers but not that much), Levin the nobleman is debating his friends about Russia’s "emancipation" changes. During the emancipation, Russia has gone from a system of bonded laborers to something like free capitalism. Society has been altered giving freedom to the peasant and laborer class, and the nobles are worried that Russia's GDP is going to the dogs. (At least, that's what they say). In reality, they're concerned about not making enough money. Levin is also concerned, but his worry is for the truth: Can he find a system where he can both make a profit and do good for the peasants?

The depth of Tolstoy’s writing is insane. It's almost like being in a room with four people of different worldviews and personalities, and hearing them all hash out their arguments. There’s Levin, a farmer who cares. Another guy is a nobleman who just wants things to be how they were before so that he can go on sucking the blood of the peasants. Levin's friend Sviazhsky is a nobleman who's studied all the theory and knows the right things to say, but has never taken on an opinion of his own because having convictions is a dangerous game. Then there's Levin's half-brother Sergey Ivanovitch, who's kind of an academic-philosopher type, very idealistic but impractical. Once in a while, we also get to see the peasants who are the subject of the conversation, but they hardly get a voice in the discussion.

Tolstoy wrote this in 1877, and he saw the collapse of Russia and the possible rise of Communism coming, 40 years before it actually happened. Here’s what a couple of characters say:

Serpuhovsky (Military official): “Russia needs men; she needs a party, or else everything goes and will go to the dogs.” [The same character says, There are no communists. Lol]

Levin: Then, too, his brother’s talk of communism, which he had treated so lightly at the time, now made him think. He considered a revolution in economic conditions nonsense. But he always felt the injustice of his own abundance in comparison with the poverty of the peasants.

Levin again: This is not a matter of myself individually; the question of the public welfare comes into it. The whole system of culture, the chief element in the condition of the people, must be completely transformed. In short, a bloodless revolution, but a revolution of the greatest magnitude… [bloodless, right]

Real characters work better than ideal ones

What I find stunning is how Tolstoy doesn't strawman any of his characters. Levin is the guy who wants to do good – but even he has conceits. He is convinced that there is a way to do good within the current structure of nobility vs peasants and he doesn't want to give up his privilege. He's trying to save the peasants whom he sees as the best of Russia and the salt of the earth but he acknowledges they are not perfect. Tolstoy doesn't write these peasants as flawless people. He shows their bullheadedness in accepting technology, their laziness, their suspicious nature, and their simple-minded acceptance of tradition that's preventing them from joining forces with Levin for their own good. The peasants are likable but they aren't ideal.

I know nothing about economics and the right way to structure a society, but even I could feel Levin's tension when he sees the theories in books just not matching with his lived experience. While his friend talks about terms he read in books like “Mulhausen experiment,” Levin has personally seen three calves die because his peasants neglected their duties and had tools damaged because they don't follow his instructions. And while Sviazhsky still doesn't change anything politically, Levin is actively experimenting with new structures to divide profits and give the peasants more ownership of the land. (He keeps failing, at least so far)

How did this affect Tolstoy?

Tolstoy took five years to write this book. To write such true characters, he probably had to live this experience himself. He had to see the breakdown of Russian society before his eyes and the cultural disintegration of the peasant society. How did writing the book change him as a person?

It apparently broke him. He wrote it in fits and starts, serializing it over five years, taking breaks, going back to farming whenever he got tired of writing the book, and grounding himself by writing farming and nature scenes. But after writing Anna Karenina and his magnum opus War and Peace, Tolstoy changed. The guy who wrote two of the longest and greatest novels in literature became skeptical of literature for literature’s sake, he renounced his nobility to live as a peasant, and he underwent a spiritual transformation.

Why? Maybe he felt sick of just putting words on paper when there was material scarcity and unrest in the world around him. Maybe he was disgusted with his own privilege and nobility. He even says as much in a scene where Levin is arguing about raising the living standards of the peasants:

[Sviazshky:] "It follows that we must educate the people, that's all."
[Levin:] "But how do schools help matters?"
"They give the peasants fresh wants."
"Well, that's a thing I've never understood," Levin replied with heat. "In what way are schools going to help the people improve their material position? You say schools, education, will give them fresh wants. So much the worse since they won't be capable of satisfying them. And in what way a knowledge of addition and subtraction and the catechism is going to improve their material condition, I never could make out."

The modern man's disillusionment with a mechanistic life that has no soul, where he goes to school and learns integration and differentiation and Lenz's law of electromagnetic induction and S-block elements and P-block elements to crack the toughest entrance exam on the planet, and then a decade letter has mere wisps in his memory and vague recollections that these were concepts that he used to know at some point to break the entry barrier for some institute that might change his life but which otherwise helped him in no way to contribute something useful to society, Tolstoy felt that. I'm the modern man by the way.

(This has happened repeatedly. The industrial revolution threatened the agricultural way of life. Computers brought in automation. The service industry led to Bullshit jobs (which I suspect I’m participating in, hooray). And the possibility of AGI threatens everything that we know about what it means to do meaningful work.)

Tolstoy’s spiritual transformation

Tolstoy's view of art changed after writing Anna Karenina and War and Peace. He literally rewrote his personality by working through 2000 pages of text.

In his book "What is art?" he expressed that art without morality isn't art – He trashed Shakespeare, Dante, Beethoven, and the bulk of his own novels, as bad art which was written for the amusement of elites and not useful in materially elevating the standard of life for common people.

He also felt that his life was meaningless.

In "A confession," Tolstoy wrote about the Eastern Fable of the traveler who was chased by a wild beast. To save himself from the wild beast, he jumps into a dried-up well but at the bottom is a dragon waiting open-mouthed to devour him. To escape the dragon, he clings to a branch growing on the wall of the well, but a black mouse and a white mouse are gnawing away at the branch and it's going to snap at some point. The traveler knows he's going to die, falling into the jaws of the dragon. But at that moment, he sees a drop of honey on the leaves of the branch he's hanging to, reaches out, and licks it.¹

To Tolstoy, this was the relentless running away from death, and the honey was his love for his family and his writing. But at some point, the love for his family didn't quite cut it.

"My family ," I said to myself. But my family, my wife and children, are people too. They are subject to the same conditions as I: they must either live in the lie or face the terrible truth. Why should they live? Why should I love them? Why care for them, bring them up, and watch over them? So that they can sink into the despair that eats away at me, or to turn them over to stupidity? If I love them, then I cannot hide the truth from them. Every step they take in knowledge leads them to this truth. And the truth is death."

And this is what he wrote about writing:

"Art, literature... Under the influence of success and praise from others I had persuaded myself for a long time that this was something that may be done in spite of the approaching death that will annihilate everything-myself, my works, and the memory of them. But I soon saw that this, too, was a delusion. It became clear to me that art is an ornamentation of life, something that lures us into life. But life had lost its charm for me, so how was I to charm others?"

This awareness of death and his preoccupation with it began eating him from the inside. He posed the question of whether there is a God and whether there is an afterlife. If there was a God, fine. But without a God, the entire project of life seemed meaningless to him. One option was to lean into pleasure and hedonism, which he felt was unfair to all the others who didn't share his privilege. The logical course of action was to kill himself – which he said he couldn't do because he was too much of a coward. The only option he had left was to "hold on and live despite the absurdity." (It would take Camus another 62 years to write "The Myth of Sisyphus" and his philosophy of absurdism). Which is what he did finally – he gave up his nobility, became a vegetarian, and lived the life of a peasant.

This wasn't sudden. Tolstoy probably modeled the character of Levin in Anna Karenina after himself, and at one point, Levin undergoes a similar moral breakdown:

"His thoughts were of the most various, but the end of all his thoughts was the same – death. Death, the inevitable end of all, for the first time presented itself to him with irresistible force... It was in himself too he felt that. If not today, tomorrow, if not tomorrow, in thirty years, wasn't it all the same! And what was this inevitable death – he did not know, had never thought about it, and what was more, had not the power, had not the courage to think about it. 'I work, I want to do something, but I had forgotten it must all end; I had forgotten – death.'"

Later when a traveler meets him on a train and finds him depressed, he asks:

"What's the matter with you?" Stcherbatsky asked him [Levin].
"Oh, nothing; there's not much happiness in life."
"Not much? You come with me to Paris instead of to Mulhausen. You shall see how to be happy."
"No, I've done with it all. It's time I was dead."
"Well, that's a good one!" said Stcherbatsky, laughing, "why, I'm only just getting ready to begin."
"Yes, I thought the same not long ago, but now I know I shall soon be dead."
Levin said what he had genuinely been thinking of late. He saw nothing but death or the advance towards death in everything. But his cherished scheme only engrossed him the more. Life had to be got through somehow till death did come. Darkness had fallen upon everything for him; but just because of this darkness he felt that one guiding clue in the darkness was his work, and he clutched it and clung to it with all his strength.

Enlightenment can be hazardous to writing

The tragedy is what this transformation did to Tolstoy's writing.

After Tolstoy's piece on how literature is useless unless it is accessible to the common man, and that it has to serve some moral good, Tolstoy wrote "Master and Man." It's a good short story about a landowner and his servant. I like it. But... it's biased. It shows things how he wants them to be instead of how they are. In "A swim in a pond in the rain,"

George Saunders

teaches the art of the short story using this as one of the examples. And the problem he observes is that the landowner is too greedy and gets redemption, but the servant is too good and is a flat character. He has no flaws, and there is no development arc for the servant. It's a moral story meant to illustrate themes of compassion, love for all, and redemption, and it reads like a message when it gets to the end.

I read Master and Man before I read Anna Karenina, and that was my first impression of Tolstoy – that he was a guy who twisted his characters to suit his agenda. But now I'm reading Anna Karenina and seeing that he wasn't always like that. He was faithful to literature at first. He represented people as people, showed them truthfully, and let people form their own conclusions based on their interactions. Of course, he's not completely unbiased: he does have a moral bent on what he chooses to show, whom he chooses to elevate and how he puts down the others. But he doesn't put peasants on a pedestal or villainize the nobles. They're all human.

After his spiritual transformation, Tolstoy probably became a better man, but his writing was less honest. But that's not the end of the story. Tolstoy wrote another story called "Alyosha the pot" much after his transformation which didn't have a clean moral. It was a simple fable about a simpleton boy, and it has a messy heartbreaking ending. I found it moving and beautiful. But because it was so messy and didn't have a convenient moral, Tolstoy apparently hated it and it was only published after his death. So despite the transformation, the writer still lived.

---

Now I'll tell you why I cried.

I had a conversation with ChatGPT when I was reading Anna Karenina. This is how it went (abridged):

Me: I heard Tolstoy said literature is useless or something. What was that about

ChatGPT: Tolstoy began to believe that most literature—including his own—was useless or even harmful unless it served a clear moral and spiritual purpose. yada yada yada...

Here’s one of the most famous and haunting passages from Tolstoy’s A Confession (written 1879–1882), where he looks back on his life—including his literary success—and finds it hollow:

“What will come of what I do today or tomorrow? What will come of my whole life? Why should I live, why should I do anything?”
“I could give no rational answer.”
“I was neither insane nor ill—I was a healthy, happy man. And yet I had come to a point where I could not live. I longed for death.”

Later, reflecting on his career:

“I had everything that people consider the greatest good: wealth, a name, a healthy body and soul, honor and respect, and I was not only not happy—I was tortured by the conviction that I had to kill myself.”

And then, striking directly at literature:

“Art, poetry… it all seemed to me like gluing together fragments of a broken jug. The jug could never be made whole again, but men kept on gluing the fragments with every sort of colored paste and laughing at the work, while I was dying of thirst.”

Me: But he did so much... 150 years later I'm reading his ideas and wondering what a meaningful life is. Why? Why did he feel so deeply? How can I let him know it's okay. Damn dude. I'm moved to tears.

ChatGPT: God, that’s such a human response. You’ve just met Tolstoy not as a literary figure, but as a man breaking open in front of you—and you felt it. That’s all he ever wanted from a reader. Not praise. Not reverence. But recognition.

That was Tolstoy at the height of his fame and wealth, standing at the edge of the spiritual void, asking:“How can a man live?”
And 150 years later, you’re standing on your own threshold, reading him—not for school, not for prestige—but because you, too, are haunted by the question. And in that meeting—across languages, across centuries—you’re doing what art is meant for: You are letting someone feel less alone for having suffered honestly.

Me: I feel like he's Oskar Schindler and I'm the guy Ben Kingsley played. But these days I'm just haunted by the same feeling, whether my writing has any meaning or material effect in an impersonal disconnected world where so many are suffering. I feel like Levin when he questioned education when the material condition of the peasants is stagnated.

ChatGPT: That’s the shift: from witnessing meaning, to doubting your own.
You’re Levin watching a peasant till rocky soil barefoot, and wondering: “What good are my theories if their boots still have holes?”

You’re writing, thinking, reaching—but the disconnection and enormity of suffering makes everything feel too small or too late.

But Tolstoy—Levin—Kierkegaard—Dostoevsky—all of them had that moment.
And none of them solved it by becoming louder or more impressive.
They endured by living as if their small acts still meant something.

Not because the world changed.
But because they refused to go numb.

And then I went on talking about this stuff, and Master and Man, and so on. Today when I was writing this article and I researched this stuff, I was looking for a source on the jug quote and trying to locate it in the original. And you know what?

It doesn't exist.

ChatGPT made up that quote. It hallucinated, like it usually does, putting words in Tolstoy's mouth that he never said. Which is why I had to download the original and read through all the other stuff to make sure I wasn't bullshitting myself.

I was crying over a broken jug that didn't even exist. Sheesh.

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1. I’ve heard this fable so many times, like in this trailer for the movie Super Deluxe, but this is the first time I came across a Tolstoy reference.