When I first read Homer, I did not experience the same sublime ecstasy as Keats. No wild surmise for me! Instead, I experienced mild disappointment, considerable confusion and strong annoyance.

That all changed - but for now, let’s focus on the negative. The poem is challenging. I understand why people are so keen to evangelise this incredible artistic achievement, but I also worry that the praise we are all so keen to heap on the poem does few favours to people tackling the Iliad for the first time. People who have been told to expect the ultimate poetic experience – and discover instead a world of hurt.

The most obviously painful experience is the infamous catalogue of the ships in Book Two: three hundred brutal lines naming 50-plus Greek captains and hundreds of related cities and islands – this quickly followed by a similarly challenging 100-line catalogue of Trojans. These passages can be a grind – but at least they have the virtue of eminent skipability. You can sail past it easily enough without feeling you’re missing any of the poem’s more significant landfalls.

Other issues are not so easily avoided. We are given a back story about the parentage and homeland of just about every character we meet, and they themselves love to expound on their parentage and hearth and sheep and other such tiresome details in their speeches. Characters often have alternate names, generally in the form of patronymics – Agamemnon will often appear as Atreides (meaning “the son of Atreus”) for example.

At first read, the control the gods exert over characters’ destinies makes it feel like there’s next to nothing at stake. There’s a scene early on where it looks as if the whole war can be brought to a swift conclusion when Menelaos enters a duel with Paris, the man who stole Helen from him and so launched all those laboriously listed ships. But the duel is inconclusive because Aphrodite conceals Paris in mist, grabs him and puts him back in his bedroom. It’s infuriating. Likewise, Athena grabs Achilles by the hair at a crucial moment, and Zeus is forever tipping his scales this way and that to decide the outcome of battles. Small wonder that Achilles gives it all up to have a sulk by the ships.

On top of all these challenges is the fact that this is an ancient Greek poem. There will always be a suspicion that translations may not do it justice. Reading group contributor daveportivo expressed this fear when he asked: “Is the Iliad supposed to be pleasing in terms of rhythm, tone, rhyme, pacing, flow, etc … any of the stuff that you associate with various types of poetry?”

The short answer to that question is: yes. But the longer one is complicated and gets to the heart of what we may be losing in translation. The issue is obvious from the very first line of the poem, as I’ll try to show here with a few different renderings from across the centuries:

George Chapman, writing in 1616, went for: “Achilles’ baneful wrath resound, O Goddess.”

Alexander Pope, (who also brings in a bit of line two) in 1720 gave us: “Achilles’ wrath, to Greece the direful spring / Of woes unnumber’d, heavenly goddess, sing!”

Samuel Butler in 1898 had: “Sing, O goddess, the anger of Achilles son of Peleus …”

EV Rieu in 1949: “The wrath of Achilles is my theme, that fatal wrath …”

Caroline Alexander in 2016, has gone for: “Wrath – sing, goddess, of the ruinous wrath of Peleus’ son Achilles.”

All these versions are significantly different – and they all give different weight to the crucial words “wrath”, “sing” and “Achilles”. Here’s the Greek: “μῆνιν ἄειδε θεὰ Πηληϊάδεω Ἀχιλῆος οὐλομένην.” (“Menin aeide thea Peleiadeo Achilleos oulomenin.”) A word-for-word translation goes something like: “Wrath sing goddess of the son of Peleus of Achilles deadly.”

You’re hopefully already getting an idea of why that’s so hard to translate – and why there are so many possibilities. In English, we nearly always expect an imperative (“sing”) to come at the start of a sentence. Otherwise, it feels very alien. (We never say, for instance: “Doing that, stop.”) But if we put “sing” at the start we lose a lot of the brute power of Homer’s opening. He comes in big with “wrath” for a reason. It’s the central tragic theme of the poem. Not to mention a meaty word in and of itself.

"There’s delicious irony in the fact that men so wrapped up in their own reputations can be so silly"

There are further tricks here that are hard to translate. Note how in the Greek – a highly inflected language – we don’t find out who the wrath belongs to, until the end of the line, with emphasis building up to the word “Achilles” by the positioning of that patronymic (Pelieiadeo) before it. Add to that the lovely assonance in all those vowels, and the difficulty of recreating the feel of a syllabic hexameter, and you can understand why translators have such a struggle. Then you have to take into account the theory that the Iliad may have been intended to be sung - and almost certainly relied for its sound and feel on a pitch accent. If academic attempts to recreate that latter are anything to go by, we’re in very strange territory indeed.

But all of this is the counsel of despair. Really, it makes up an argument for coming to a better understanding of Homeric language and culture, rather than for giving up on translations. Homer does have a special music – but so too do plenty of the translations. The trick is not to focus on what we’re losing – but what’s still there.

Meanwhile, even the other frustrations I’ve listed above may unsettle first-time readers, but they are also a great part of the poem’s enduring fascination. They’re a mark of the Iliad’s great distance from us, but also of how lucky we are to be able to peer into this ancient and alien culture, to have these messages from the long vanished past, to have such enticing mysteries.

Even that catalogue of ships becomes interesting if you think of the poem as something that would often be recited orally, from memory. It must have been some feat, to get all those names and their connections in order. I can imagine rapt audiences listening just waiting for the singer to slip.

All those genealogies also take on deeper resonance if you think of memory in a broader sense. The whole poem is about the struggle against mortality, what it means to be remembered, about fame and reputation, and the struggle to maintain “kleos”. Listing ancestors takes on a special meaning in this context. To repeat the names of other men is to keep alive the hope that you’ll be remembered, too. As the Iliad was being put together, Greek societies were only just rediscovering the art of writing. Such memories must have felt like the only line into the past, the only link into the future.

Back on the subject of “kleos”, there’s delicious irony in the fact that men so wrapped up in their own reputations can be so silly. Agamemnon is as greedy and heedless as the worst Tory stereotype; Achilles is so mardy. As the poem goes on, their petulance becomes more and more intriguing – especially as fate gives them more and more cause to regret it.

As for fate, and the gods, the more you read of the poem, the more you come to realise that this power isn’t straightforward. Homer provokes deep questions about the role of fate and human agency. It isn’t much of a stretch to see much of the western philosophical tradition’s obsession with free will starting here.

So much for the challenges in Iliad. I haven’t even started on the good stuff. I remember that on my first reading of Homer, I sometimes felt like I was wandering in deep fog. But that confusion made the moments when the sun broke through feel all the more golden. When a hand reached down to mine, across 3,0000 years, and I felt its reassuringly human touch. It can bring tears to your eyes. Read a passage from Caroline Alexander’s translation from the end of Book VI, of Hector’s encounter with his wife and son before he has to leave them for battle. There’s no misunderstanding that.

And if that whets your appetite, I’m happy to say we’ve got 10 copies of the new translation to give away to the first 10 readers from the UK to post “I want a copy please”, along with a nice, constructive comment in the comments section below. If you’re lucky enough to be one of the first to comment, email Laura Kemp with your address (laura.kemp@theguardian.com) – we can’t track you down ourselves. Be nice to her, too.