Chasing My Hat Through 12 Classic Novels

Read Along with My 2026 Reading Plan—and the Tenuous Theory Holding It Together

“I have read today . . . some ten pages of Tristram Shandy,” wrote C.S. Lewis to his friend Arthur Greeves in 1916, “and am wondering whether I like it.” Why the hesitation? “It is certainly the maddest book ever written. . . . It gives you the impression of an escaped lunatic’s conversation while chasing his hat on a windy May morning.”

Detail from Roman Kramsztyk‘a portrait of the Polish poet Jan Lechoń. Source.

As it happens, I’ll be reading Tristram Shandy this year. And the hat I’ll be chasing, hopefully not like a lunatic? I’m hoping to follow a thread through this and eleven other major classics—what I affectionately call big-ass classic novels—one per month.

• January: John Steinbeck, East of Eden

• February: Wilkie Collins, The Woman in White

• March: Fyodor Dostoevsky, Crime and Punishment

• April: Charles Dickens, David Copperfield

• May: Henry Fielding, Tom Jones

• June: Laurence Sterne, Tristram Shandy

• July: Miguel de Cervantes, Don Quixote

• August: Herman Melville, Moby-Dick

• September: Leo Tolstoy, War and Peace

• October: Vasily Grossman, Life and Fate

• November: Denis Johnson, Tree of Smoke

• December: George Eliot, Daniel Deronda

Is there a common thread running through these books? Of the list, I’ve only read East of Eden so far—just finished a few days ago—but as I researched and assembled the list I hunted for thematic elements that might link them. Based on summaries and secondary reading, here’s my best guess at the thread that holds them all together.

The year begins where so many stories begin: Cain and Abel. In East of Eden Steinbeck reworks the Genesis account in the arid hills of Salinas, California, not far from where I grew up. The story turns on a linguistic debate, the meaning of the Hebrew word timshel, “thou mayest,” and its implication for the moral agency of its characters.

“Humans are caught—in their lives, in their thoughts, in their hungers and ambitions, in their avarice and cruelty, and in their kindness and generosity too—in a net of good and evil,” explains Steinbeck’s narrator. “I think this is the only story we have and that it occurs on all levels of feeling and intelligence. Virtue and vice were warp and woof of our first consciousness, and they will be the fabric of our last, and this despite any changes we may impose on field and river and mountain, on economy and manners. There is no other story.”

Reductive? Maybe. But that would seem like a good place to begin thinking of the thread that holds these novels together, particularly the question of the many characters’ moral agency. “Timshel!” as Adam Trask bellows. Personality, inheritance, circumstances—none of these equate to destiny; humans have the freedom to choose. And the issue of moral freedom sets the terms for most of what follows.

Wilkie Collins’s Victorian thriller The Woman in White comes next in February. The primary villain, Count Fosco, is brilliant and charming and has decided these qualities exempt him from the rules that govern the rest of us lowly humans. He represents what happens when someone decides that “thou mayest” means “thou mayest do whatever thou canst get away with.” He’s what Cain might have been if the primeval killer had a better alibi and a talent for witty conversation.

Then comes Dostoevsky’s Crime and Punishment in March. Like Fosco, Raskolnikov believes he floats in a moral atmosphere somewhere above we dull, dimwitted mortals—and tests the theory with an axe. The rest of the novel is what happens when timshel runs headlong into the consequences: the discovery that choosing evil doesn’t make you exceptional, only guilty and tortured. Theoretically, the shift from Collins to Dostoevsky takes us from entertainment to reckoning; we’ll see how it goes this time; I started the novel once before and abandoned it.

By April, I’ll have been living in Raskolnikov’s claustrophobic conscience for a month. God help me—and you, too, if you choose to read through these novels with me. I invite you to do so! We’re going to need a breather, and I think Dickens’s David Copperfield might be just the thing. David is buffeted by cruelty and loss and the accidents of those who raise him and abandon him. Yet the novel insists he’s more than what’s been done to him. Will he become, as David famously asks, “the hero of my own life”? Thou mayest, we might reply; you’ve got about a thousand pages to do it.

Collins, Dostoevsky, and Dickens were all contemporaries. Dickens and Collins were actually friends. For May, I want to jump back in time a bit to an earlier period of the novel. Henry Fielding is Dickens’s literary grandfather and helped lay the foundation for the English comic tradition. I’m guessing reading Tom Jones after David Copperfield will help show some of the family resemblance. What does thou mayest look like when the character is impulsive, congenitally amorous, and lacks decorum and self-reflection? I’ve seen the masterful BBC adaptation—twenty or so years back—so I recall the answer in broad outline. You get the sense Fielding believes most folks will muddle toward decency if you let them—plenty of people try to thwart Tom. I’m eager to see how the comedy plays on the page.

Then comes June, and we’re back to chasing our hat with the lunatic. In Tristram Shandy. A near-contemporary of Fielding, Laurence Sterne is less the grandfather of writers like Dickens and Collins and more like the crazy uncle whose private enjoyment is embarrassing the family. He’s less interested in what his characters choose than in whether choice can even be narrated coherently, and he scrambles every attempt through comic digression, interruption, and typographical mischief. If timshel assumes a self capable of choosing, Sterne wonders whether that self can even get its story straight: not “thou mayest” but “thou mightest, if thou couldst puzzle out what thou wert doing in the first place.”

The absurdity continues into summer and also introduces us to a pair of questers. First up in July is Cervantes’s Don Quixote, whose title character is addled by chivalric romances and decides to become a knight-errant. Don Quixote’s freedom takes the form of refusal—refusal to see windmills as windmills, peasants as peasants, or the world as it is. When it comes to madness, is timshel a delusion or something more?

In August, we get our second quester. Herman Melville’s Moby Dick presents Quixote’s dark double in the form of Captain Ahab, a relentless monomaniac whose search for the whale gobbles him whole. Whereas Quixote’s madness is comic, Ahab’s is apocalyptic. Both men decide the world is wrong and they are right; both follow that conviction to the end. But as a reminder that our freedom implicates others, Ahab is responsible for the crew of his ship, the Pequod. Sometimes a man tilts at windmills and wounds mostly himself; other times he drags the whole ship down with him.

Our heaviest months come in fall with another pairing and another version of the question. Tolstoy’s War and Peace (September) and Vasily Grossman’s Life and Fate (October) both ask whether individual choice means anything at all against the grinding machinery of history. Napoleon’s invasion of Russia, Hitler’s siege of Stalingrad—what room is there for thou mayest when artillery is firing? And what responsibilities do we bear when moral choices are pressured by such external forces? As the world grows large and menacing, perhaps our freedom is best expressed in small rebellions of mercy, personal decency, and integrity.

Yes, but isn’t that book too small?

In November, Denis Johnson’s Tree of Smoke, the most recent novel in my project, pushes our inquiry into the American catastrophe in Vietnam. What happens to the actors when their nation convinces itself of its righteousness and then faces a conflict that undermines its myths? As the fog of war descends on soldiers, spies, missionaries, and others, Johnson’s characters choose, but the moral implications of those choices dissolve in the chaos. Thou mayest, but it’s hard to tell what difference it makes.

December closes out the year with George Eliot’s Daniel Deronda, a novel about vocation. Daniel spends the book groping toward his purpose—not just whether to choose, but what to choose for. When he discovers his Jewish heritage and commits himself to a Jewish national future, it reorients his life. Eliot suggests that timshel is incomplete without direction: “thou mayest” needs a “toward what?”

That is the arc this list presumably traces: Cain’s freedom ends with Daniel’s vocation. Not every book asks the same question in the same way; Sterne is more interested in narrative derailment than ethics, and Tolstoy and Grossman spend as much time on history and contingency as on individual moral dilemmas. But if I’ve understood them, all these novels seem to present variations on a theme: we all have some measure of freedom, however constrained and compromised, and our lives are judged by what we do with it.

Time will tell if that thread actually materializes as I imagine, or if I’ll just be chasing my hat. You’ll have to tell me, and I invite you to join me each month in reading these novels and following the trail. Thou mayest, you know.

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