A Pilgrimage to the Unreadable Three

Letting Difficult Books Change You

There are books we read for pleasure, books we read for understanding—and then there are the ones we circle for years, unsure whether we’re ready. This is a reflection on those unreadable books: the ones that sit on the shelf like questions, which change us even before we’ve opened them. I didn’t buy them as a challenge. I bought them because they whispered something I couldn’t quite name. This is the shape of that listening.

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About a year ago, I bought four books in one go: Moby-Dick, Gravity’s Rainbow, Ulysses, and Infinite Jest. I didn’t know it at the time, but that small stack would come to shape the way I read—and maybe even the way I write. They’ve stayed on my shelf ever since—not quite gathering dust but gathering presence. Watching. Waiting. Not with urgency, just quiet persistence. A kind of invitation I hadn’t yet answered.

I started with Moby-Dick. It was slower than I expected, but not in a bad way. It wandered. It lingered. And though its rhythm was gentle, I still found it hard-going at times—not because the story was unclear, but because the language and style felt foreign to me. Long sentences, archaic phrasing, chapters that drifted into essays about whaling tools and rope—it was like listening to someone speak in an accent you mostly understand but can’t quite predict. But I stayed with it. I didn’t skim. And I started to see that the unfamiliarity was part of the reward. It slowed me down. It taught me how to stop expecting every paragraph to deliver a plot point. It trained a different kind of attention in me—the kind that doesn’t demand progress, just presence.

It was the first time I realised that a book could be more than a story—it could be a space. Something to inhabit. Something to be shaped by.

Then came Gravity’s Rainbow. That one didn’t wander—it erupted. From the first page, it made no effort to meet the reader halfway. Characters slipped in and out without warning. Plot threads scattered like static. Whole chapters twisted into song, hallucination, pornography, slapstick. It was confusing. Sometimes exhausting. At times, it felt like Pynchon was daring you to keep up, writing circles around you just to remind you how wide his reach was.

I’ve heard others say the same—that Pynchon knew exactly how much he knew, and that part of Gravity’s Rainbow is the performance of that knowledge. But the more I read, the more I sensed that the difficulty wasn’t just showing off—it was part of the book’s design. The disorientation, the overload of information, the refusal to resolve into clarity... it all mirrored the world he was writing about. A world splintered by war, by systems too large to understand, by technology we couldn’t control. Reading it felt less like interpreting a message and more like weathering a storm.

And that made it feel like a natural extension of Moby-Dick, strange as that might sound. Both books made me uncomfortable in some way—one through unfamiliar language, the other through conceptual chaos—but both asked me to sit still with the discomfort. To keep reading anyway. To let go of control. That’s a kind of reading I didn’t know I was capable of until I’d done it. And it changed something in me.

I’ve been thinking about reading Gravity’s Rainbow again—not to understand it better, exactly, but to see what it shows me now. I haven’t started it yet. At the moment, I’m sitting in the pause between books. Reading other things. Letting the deeper current gather.

Right now, I’m partway through J.R.R. Tolkien: Author of the Century by Tom Shippey and The Redemption of Althalus by David and Leigh Eddings. They’re very different reads—one a slow excavation of myth and language, the other a straightforward, magical adventure—but both keep me close to story. They remind me that reading doesn’t always have to strain. It can also flow. I think I’ll read more like that before continuing the sequence—maybe a short novel, or a piece of science fiction that expands rather than tests me. Not to escape, but to recalibrate.

Because next will be Ulysses. And after that, Infinite Jest. I’ve placed them deliberately, not just in difficulty but in spirit. Gravity’s Rainbow comes first—chaotic, fragmented, paranoid. Ulysses follows—not simpler, but steadier, more formal in its playfulness. And then Infinite Jest to finish—modern, recursive, emotionally raw. It feels like a strange but satisfying arc: from collapse, to form, to feeling.

I know Ulysses is structured around a single day in Dublin, but that it stretches and reshapes that day into something mythic and shifting. The voices change. The style morphs. Even punctuation bends under the weight of what it wants to express. I don’t expect to understand all of it. But I want to walk through it slowly, like moving through a dream of a city I’ve never been to.

And Infinite Jest... that one still makes me hesitate. Its length. Its footnotes. Its loops and timelines. I’ve heard it’s about addiction, about entertainment, about loneliness and compulsion. But I’m not reading it for the themes, exactly. I’m reading it for what it might do to my thinking. For what it might open up in me—not just as a reader, but as a writer.

Because that’s part of why I’m drawn to these books in the first place: I want to grow. I want to be challenged. I want to see what happens when I hold my attention against something that doesn’t yield easily. I don’t expect them to give me answers. But I do think they might offer rhythm. Texture. A way of thinking that doesn’t flatten things too quickly. I don’t plan to imitate their styles—how could I? —but I do hope they’ll change the way I hear sentences. The way I place one thought after another. The way I hold space for complexity in my own writing. These books are part of how I’m teaching myself to write.

That’s the shape of this pilgrimage. It’s not about conquering the unreadable. It’s about walking alongside it. Letting it change the pace of my mind. Letting it show me something I couldn’t have seen otherwise.

Because these books don’t just ask for time. They ask for presence. They don’t want to be skimmed. They don’t want to be “got.” They want to be lived with. And in a world that pulls us toward speed, toward opinion, toward mastery—there’s something rare and quiet in simply sitting with a book that might never fully reveal itself.

In that way, reading like this begins to feel less like consumption and more like resistance. In a culture obsessed with clarity and brevity, choosing slowness—choosing confusion, even—is its own act of attention. These books have helped me remember how to linger. How to resist the urge to finish just so I can move on to the next thing. They’ve taught me that meaning doesn’t always arrive on schedule.

Some days I catch myself looking at them on the shelf—Ulysses, Infinite Jest—and they feel like presence more than objects. Not inert, not ornamental. Just there. Waiting. They don’t demand anything. But they don’t disappear either. It’s strange, really, how books you haven’t even read yet can still shape the way you think. As if just being near them rearranges something in you. As if they already know something about the kind of reader you’re becoming.

There’s something else I’ve come to realise along the way: that reading outside your comfort zone takes a certain kind of nerve. Not because the books are intimidating—though they are—but because they challenge the version of yourself you’ve grown used to. The reader who always understands, always moves smoothly from sentence to sentence. These books don’t let you stay there. They ask you to become a different kind of reader. Maybe even a different kind of person. And that takes more than patience—it takes a willingness to feel uncertain, and to stay anyway.

And even if I don’t finish them, I think there’s no harm in trying. Just reaching for a book like this opens something up. The simple act of choosing difficulty—not to conquer it, but to spend time in its company—feels worthwhile. Every unread page still teaches me something. Every attempt is a gesture toward growth.

So, I’m not reading them to impress anyone. I’m not trying to be clever or literary. I’m reading them as I am—without credentials, without certainty, but with care. With curiosity. With a willingness to be changed by what I don’t understand.

And I think that’s enough.

I know I’m not in for an easy time. These books are complex, tangled, and often overwhelming by design. But I’m not looking for ease. I’m looking for what comes after it—for what a page asks of you when you stop demanding that it explain itself. I’m ready to read in that spirit. Patient. Unhurried. Willing to sit with what resists me, and to listen anyway. If there’s clarity, it’ll come. If there’s meaning, I’ll meet it on its terms.

If you’ve got books like these on your shelf—ones that seem too long, too strange, too tangled—maybe this is your sign. You don’t have to be ready. You just have to be willing. Willing to begin slowly. Willing to pause. Willing to stay open, even when the pages go dark. That’s where the real reading starts.

Until next time.

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