Would Odysseus Have Made It Home Sooner With an AI?

If you visit Roske.AI this week you’ll find me dressed as Odysseus, which requires some explaining. My website completely rebuilds itself every Saturday at 5AM around whatever pop culture thing is distracting me (I let the AI pick, which is a whole other post), and this week it picked Christopher Nolan’s Odyssey, which opens Friday, July 17, shot entirely on IMAX film, with Matt Damon playing a man who takes 10 years to finish a 2-week boat trip. So I’ve spent the week staring at a heroically muscled version of myself (the muscles are aspirational) and turning over one question: would Odysseus have gotten home faster with an AI?

I keep landing on no, and the reason is the part worth talking about.

The thing everybody forgets about the Odyssey is that the man already had the oracle. He sailed to the literal edge of the underworld to consult Tiresias, who told him (in plain Greek, no riddles) exactly how to get home and exactly what would sink him… don’t touch the cattle of the Sun. Circe gave him a complete operational briefing on the Sirens, the strait, the works. He had prophecy on tap, an answer key in hand, divine consulting engagements at below-market rates, and he still turned a 2-week trip into a decade. Read it as an adventure story and it’s thrilling. Read it as a data scientist (I can’t help it, I have the degree) and it’s a 10-year case study in a brilliant man ignoring good information.

Go through where the trip actually went wrong and almost none of it was a missing-data problem. The bag of winds is my favorite example, cause it’s the cleanest: Aeolus hands Odysseus a literal shortcut home, every contrary wind tied up in one sack, and within sight of Ithaca (they could see the island!) his crew decides the bag must be treasure the boss is hiding from them, opens it, and blows the whole fleet back across the sea. The crew had every piece of information they needed. What they didn’t have was trust in the man holding the bag, and if you’ve never watched that exact scene play out in a company, you haven’t sat through enough reorgs.

The cattle of the Sun is worse. Tiresias warned him, Circe warned him, Odysseus repeated the warning to his own crew personally… and then everybody got tired and hungry, the boss fell asleep, and they had a barbecue. They knew the answer and did the other thing, which (lets be honest) is most of us with most answers.

Even the Cyclops mess was a question problem. Odysseus asked “how do I beat this monster” when the better question was “how do I avoid ever meeting him,” and then, having won, he couldn’t resist shouting his real name at the giant from the boat, which is how you get a god mad at you personally. (Edward, you’ve literally done the conference version of this… won the argument, then kept talking until you un-won it. The man taunted a Cyclops and you’ve taunted Q&A sessions. Same energy, fewer shipwrecks.)

Now, a modern AI is Tiresias with better uptime. Nobody sails to the underworld anymore: you ask, and you get a competent answer about almost anything, instantly, for about the price of a sandwich a week. I build these tools for a living (AgentCube talks to Essbase and Oracle EPM precisely so finance teams can ask and actually get answers), so I’m the last person alive who’ll tell you the oracle doesn’t matter. It matters! When a decent answer costs almost nothing, you can afford to ask 10 questions where you used to ration one, you can model the strait before you sail it, and you can catch the obvious mistake before your crew opens the bag.

But look at what the oracle never fixed, in 1200 BC or now: asking the wrong question, and ignoring the answer you didn’t like. I watch teams buy the oracle and expect the epic to get shorter, then ask “how do we win this quarter?” when the honest question was “are we even sailing toward the right island?”, and the model cheerfully helps them go faster in the wrong direction, cause that’s what it was asked to do.

And the tell is how the story actually ends. What finally gets Odysseus home isn’t a better oracle: it’s that he lands in Ithaca disguised as a beggar and, for once in his life, shuts up. He asks the swineherd what’s been happening, and he actually listens, and only after he understands the room does he string the bow. The least cinematic stretch of the whole poem is the part where he finally behaves like a good interviewer, and it’s the only stretch where everything goes right.

So: would Odysseus have made it home sooner with an AI? Only if he’d used it to ask better questions instead of to win more arguments, and for 9 of those 10 years, he wouldn’t have.

If somebody handed you the oracle tomorrow (they have, by the way… it’s $20 a month), what’s the question you’ve been avoiding asking it? Write me (Edward@Roske.AI). I’d genuinely like to know, and unlike Tiresias, I answer the same day.

Asking good questions, Edward