Rediscovering the classics at almost 40

There’s a peculiar injustice in how we’re introduced to the great works of literature: too soon, and under duress. We read Candide and Gatsby when we are barely able to drive, let alone navigate the subtext of irony or existential despair. We sit in classrooms, staring at chalkboards, while teachers insist that these books are masterpieces. Maybe they are, but how can we tell? At 16, I was more interested in whether anyone noticed my fresh pair of Dr. Martens boots while running in the school garden than in Voltaire’s take on Leibnizian optimism.

And so, these books become schoolwork. In the Italian school system we read them just enough to write the essay or get a good mark at the interrogazione, the oral quiz. And then, we discard them. It’s only later—if we’re lucky—that we give them another shot, this time with a mind sharpened by a few decades of disappointment, a little tragedy, and perhaps a mortgage.

I started this literary reparation with Candide, a book I barely remembered beyond a vague impression of absurdity. Rereading it now, it’s clear: Voltaire was having the time of his life. Candide is a satire so acute that even today, it reads like a contemporary send-up of self-help culture. Pangloss, with his idiotic refrain—“all is for the best in this best of all possible worlds”—isn’t so different from the LinkedIn guru posting about “embracing the grind.”

At 16, I thought Candide was a simple fool. Now, I see that his naive optimism isn’t stupidity, but survival. He clings to Pangloss’s nonsense not because it’s true, but because the alternative—accepting that the world is indifferent, often cruel—would be unbearable. That hits differently at 39. The jokes still land, but now they carry weight.

Next up: The Great Gatsby. This one, perhaps courtesy of the 2013 big screen adaptation starring Leonardo DiCaprio, I remembered better. Or thought I did. Back in high school, Gatsby was presented as a tragic hero—an American dreamer undone by his own idealism. We were asked to admire him, in a way, as if his longing for Daisy were noble rather than pathological. But reading it now, I have a different take: Gatsby isn’t a romantic, he’s a real estate developer with a stalking problem.

Daisy isn’t his great lost love; she’s an accessory, an imagined endpoint to his reinvention. Gatsby isn’t in love with Daisy. He’s in love with a version of himself that never existed. And the tragedy isn’t that he loses her—it’s that he never stood a chance, because the man he was pretending to be was a fantasy all along.

It turns out, these books weren’t the problem. The problem was reading them before we had any context for them. Before we’d been heartbroken or humiliated, before we’d worked jobs we hated or made choices we can’t undo. Literature is wasted on the young, because understanding it requires mileage.

So now I’m working my way through the syllabus. The Picture of Dorian Gray is on the list. Dubliners might be next, now that I can appreciate the brutality of ordinary lives, the paralysis beneath small talk, the pain in things left undone. And I’ll get to War and Peace, eventually—probably by the time I’m 50.

Perhaps that’s how it works: read the classics twice. First when you’re too young to understand them, and again when you wish you didn’t.