This essay explores why poetry is difficult, especially when we seek comfort in art and are instead met with resistance. Through a personal encounter with T.S. Eliot’s The Waste Land, it reveals how challenging poems can become companions in emotional and existential healing.
How Eliot’s Difficult Poem Found Me in Rehab
I met T.S. Eliot in lockdown.
Not literally, of course, he didn’t shuffle into group therapy or slide a smuggled cigarette across the table, but his ghost was there, that thin, angular, and a little aloof poet who looked like he had such a hard time in social circumstances.
He arrived by way of a kid who couldn’t have been more than sixteen, wild curly hair and it was clear he had been some sort of emo or goth in his real life, because all of his clothes were black band tees.
I sat next to him in our English class, in the back of the room, where we weren’t supposed to talk but he and I had started writing poems individually so we would share our favorite poets from the literature textbooks rather than doing our work.
I was so taken by Dylan Thomas at the time and he was a devotee of Eliot, two seemingly opposing forces undercutting those first generation modernists.
Where Thomas had this beautiful and powerful felt sense of language, Eliot seemed heady to me, and someone lost in his own intellectualism.
Through Matt in the back of that rehab in nowhere Utah I found The Waste Land; he said it had saved him like some sort of sermon as if the voice which lived inside the poem, that voice which was cracked and composite and barely stitched together, somehow mirrored his own.
Some poems are mirrors. Others are knives. But the rarest become companions.
Reading The Waste Land for the First Time (And Failing)
Because he said it had such a profound impact on him, I wanted to understand the poem, but as any first-time readers of it, I failed miserably.
Thats one of the first reasons why poetry is difficult, oftentimes some poetry doesn’t always want to be understood on your terms, it resists you.
I hope I never forget the first time reading that poem, that green cover, and those first few lines, “April is the cruelest month…” and immediately hitting a wall, immediately feeling lost.
Unless you have a deep understanding of poetic tradition, the first line immediately throws you off, why is April in this poem and why is it cruel?
That first experience of the poem felt like trying to eavesdrop on the afterlife, just fragments humming and foreign languages I didn’t know and obscure references with tonal shifts that offered really no explanation at all; I found myself in a state of constant confusion.
Why Poetry Isn’t Always Meant to Comfort You
I didn’t return to Eliot for years because of this confusion, not until a college survey class on Modernism offered me a second encounter.
We were exploring High Modernism through Stein and Joyce and Pound, a curriculum of fractured people writing in fractured sentences to survive the fractured times they found themselves in.
And by that time I’d lived more and lost more, broken more and something deep had opened up inside of me, so that what once felt chaotic in the poem suddenly felt honest; the poem hadn’t changed but I certainly had and I saw that Eliot wasn’t trying to create a map out of descent, he was mapping the ruins themselves.
The poem hadn’t changed. I had.
That’s when it clicked that maybe comfort had never been the goal, and that my ideas around clarity and understanding were getting in the way of the experience.
I was bringing expectations to the poem, rather than letting it reveal itself.
The Power of Art That Refuses Explanation
Some art doesn’t beg for understanding. It doesn’t hold your hand. It just is.
Later, in a seminar on Language Poetry, an avant-garde movement from the 70’s and early 80’s that treats language itself as the primary subject of the poem, I met poets who celebrated the ideas of difficulty.
Some of these poets become my all-time favorites, Clark Coolidge, Susan Howe, Lyn Hejinian.
By this time, I had started to see that the poem wasn’t about me, in that discomfort around difficulty and understanding didn’t mean that the poem had failed, it just meant that I wasn’t in control of the meaning-making.
And that’s the second reason why poetry is difficult, because sometimes poems refuse your own need for resolution.
Sometimes art doesn’t ask for your understanding nor does it attempt to do anything to you, sometimes it just is.
Read more about the power of a poem that just is.
How T.S. Eliot Became My Unlikely Teacher
Thus I began to experience difficult poetry the way I saw grief, or depression, or love at its hardest, and most intense, not as a puzzle to figure out, but as a condition of being, a field you stand in, a weather system.
I mean you don’t ask a thunderstorm to explain itself, you simply listen and live through it.
The more times I experienced The Waste Land the more I let the poem have me, rather than trying to decipher it, and I began to see in him a familiar presence and a companion who challenged me and held me in whatever way I needed.
Poetry as a Practice of Emotional Endurance
This practice of returning to this difficult piece of art was ultimately not intellectual, but spiritual; to sit inside this poem that refuses closure, or let alone a single voice or register, is to practice a form of remaining, to stay when you don’t understand.
To read him in this work is to dwell with a voice that doesn’t owe you anything, and can actively resist your attempts at meaning-making.
And this practice of attention has bled into other parts of my life, a season of depression or a relationship on the rocks, those times in life where there are questions without answers.
Eliot taught me how to remain when nothing resolves, and that is perhaps the deepest reason why poetry is difficult, in that it mirrors the truth that life does not always explain itself.
To sit inside a poem that refuses closure is to practice remaining.
Why Some Poems Are Meant to Resist You
Over time, The Waste Land became less a text and more a space I enter, not as something finished and monumental like a sanctuary or a museum, but like a room in the back of the house, unfinished and always unsettled with a light that shifted depending on the person I had become.
If the poem ever felt easier, it wasn’t because it had softened; it was because I had grown strong enough to hold its weight and trust its discomfort.
There are still days I want a poem to take my hand and lead me somewhere safe, but those are not the poems that I’ve come to trust.
The poems I trust are the ones that don’t flinch, that leave me with more questions and echos and awe.
If you’re still wondering why poetry is difficult, it’s because life is too, and the poems that matter most are the ones that teach us how to stay inside that difficulty without retreating.
If you can let go of our instinctual need to understand and let a poem teach you, it’ll show you how to live.
It probably won’t teach you how to succeed or win but it will certainly teach you how to bear ambiguity, and how to breathe inside of contradiction.
Sometimes a poem can operate like a mirror and other times it can cut with truth like a knife, but the rarest poems, the ones we keep returning to, become companions who walk with us and grow with us.
The difficulty of a poem is not a wall, like my first time reading The Waste Land, it is actually the shape of a door, and the act of returning to it again and again is how we learn to walk through, even if we never find the other side.
If you’re wondering why poetry is difficult, maybe it’s because life is too.
What’s a poem, book, or work of art that once made no sense to you but wouldn’t let you go? I’d love to hear what found you when you were ready.
Craving a deeper dive into how language becomes a tool for survival? Explore the full framework in Poetry for Emotional Healing, your guide to reading as renewal.
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Dr. Samuel Gilpin is a poet and essayist who walked away from the academy to write at the edge; where poetry meets philosophy and transformation starts with ruin. At samuelgilpin.com, he explores the deep architecture of change, not with hacks or hype, but with language that sharpens and thought that lingers. He holds a PhD in English literature, but what he offers isn’t academic; it’s personal, raw, and precise. When he’s not writing, he’s reading Eliot for the hundredth time, rewatching The Wire, or lifting weights. Download his free guide, Dangerous by Design, and start reading like your mind depends on it. Or sign up for his free course, The 5-Day Poetic Reset.
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