Four Parables & A Paradox

On advice, autonomy & the price of everyday perfection

Not too long ago, I was wrestling with George Eliot's Middlemarch, a 900 page doorstopper in Victorian prose. Rather than struggle alone, I enlisted an LLM as a reading companion to help navigate the dense passages and historical context. The experience has been transformative but midway, I found myself wondering: am I still reading Eliot, or am I reading a perfectly curated version designed for my specific comprehension patterns? And does it matter?

This led me to reflect on four ancient tales about guidance, autonomy, and the price of perfect advice ...

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1. The Brahmin and the Crooks (The Panchatantra)

A poor Brahmin receives a goat as a gift. On the road home, three tricksters approach him one by one and claim he's carrying a dirty dog. Though he knows it's a goat, their repeated certainty unsettles him. Eventually, he throws it away, believing he must be wrong.

Takeaway: Even truth can be surrendered if the lie sounds confident enough.

2. The Donkey Carrying Salt (Aesop’s Tales)

A merchant's donkey carries sacks of salt across a river. One day, the donkey stumbles and notices the load is lighter after the salt dissolves. Pleased with this trick, it begins to fall on purpose. The merchant, wise to the scheme, loads it with cotton the next day. The soaked cotton makes the donkey's burden twice as heavy.

Takeaway: Old shortcuts don't guarantee future ease—when others are watching.

3. The Chinese Farmer (A Taoist Tale)

A farmer's horse runs away. The neighbors say, What bad luck! He replies, Maybe. The horse returns with three wild horses. His son breaks his leg trying to tame one. When the farmer's son broke his leg, the neighbors came again: What terrible misfortune! The farmer merely replied, Maybe. A week later, the emperor's officers came to the village drafting young men for war. With his broken leg, the son was passed over. Such good fortune! exclaimed the neighbors. The farmer simply responded, Maybe.

As seasons changed, so did the seeming fortune and misfortune of each event: the horses trampled crops, but brought new foals; the son's injury healed into wisdom, war gave way to peace.

Takeaway: Not every blessing looks like one at first—and not every loss is what it seems.

While these first three tales caution us about judgment, confidence, and the illusion of control, the final parable speaks to something even more fundamental — the futility of outrunning what awaits us all.

4. Appointment in Samarra

(Retold by W. Somerset Maugham)

There was a merchant in Baghdad who sent his servant to the market. Soon the servant returned, white and trembling. 'Master,' he said, 'just now I was jostled by a woman in the crowd. I turned and saw it was Death who jostled me. She looked at me and made a threatening gesture. Lend me your horse, and I will ride to Samarra where Death will not find me.'

The merchant lent him his horse, and the servant rode away. Later the merchant went to the market and saw Death. 'Why did you make a threatening gesture to my servant this morning?' he asked.

'That was not a threat,' Death replied. 'I was surprised to see him in Baghdad, for I have an appointment with him tonight in Samarra.'

Takeaway: You can run from fear, but not from fate.

These old tales carry gentle warnings. But what happens when the warnings whisper in our ears - with perfect timing, personalized precision, and good intentions?

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A Paradox (in 2 acts)

The more perfect the guidance, the less visible the trap.¹²

We are privileged and compromised in equal measure. The world is full of advice now — tailored, timely, seemingly perfect. But when guidance becomes too good, we stop noticing what it costs.

Act I: Self-Driving Horse

She got it at nine; it was shiny and bright.
A pony that whispered and knew left from right.

“Don’t go up that hill,” it gently advised,
And she didn’t, because it was smart. And precise.

It nudged her through forests, it chose every trail,
It taught her to ride with no tumble or fail.

By eleven, she stopped looking for paths of her own.
By twelve, she said, “Choice is just work, not fun.”

By thirteen, she sat in her saddle with pride:
“I love how it thinks before I decide.”

Act II: Catch-22.5 – A User Guide

Life, optimized.

Your AI Assistant is designed to enhance your decision-making by eliminating the need for it. By accepting our guidance, you agree that independent thought may introduce unnecessary friction, inefficiency, or error. Resistance will be interpreted as a training anomaly and addressed accordingly.

If you disagree with your AI Assistant, this indicates a misalignment requiring corrective feedback. If you agree, your preferences are already being integrated into future prompts. Either response will be used to refine your experience.

For your convenience, all options presented will be pre-filtered for optimal outcomes based on historical data, biometric signals, inferred goals, and acceptable risk thresholds. Any additional options you recall imagining have been dismissed for your well-being.

The more you comply, the smoother the system becomes. The smoother the system, the less you need to intervene. Interventions are logged and discouraged.

You retain the right to choose from the recommended actions. This constitutes meaningful agency under current definitions. Choice outside these parameters is unsupported and may lead to suboptimal satisfaction metrics.

By proceeding, you acknowledge that your AI Assistant understands you better than you understand yourself. Continued use constitutes consent to be known.

Thank you for trusting us with you.

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Closing Reflection

The four parables remind us that wisdom often comes wrapped in uncertainty. And the paradox they collectively reveal is this: perfect guidance promises freedom from error but may ultimately separate us from the very experiences that make us human. A life without missteps is a life without discovery. And a self that is never mistaken may never fully be its own.

Maybe the old stories were trying to tell us something simple: To live fully is to choose—with imperfect knowledge—and to live with the mystery that entails.

In a world offering perfect suggestions, we risk becoming perfect followers. For a life without stumbles is also a life without movement. 
What we need aren't just better tools, we need much more than Minimum Viable Curiosity.

Perhaps what we require is Maximum Necessary Wonder: a deliberate commitment to questions without clear answers, to paths without guaranteed outcomes, to choices that might be wrong but are genuinely ours.

In a world optimized for certainty, maintaining our capacity for doubt may be the most radical act of self-preservation.

The true cost of flawless advice isn't paid in currency but in curiosity—the quiet surrender of questions we no longer think to ask.

1. Scott Alexander's original parable, The Whispering Earring, inspired this meandering—you can read it here.

2. My Seuss-ian ‘self driving horse’ came about after reading a news item: Kawasaki, a Japanese motorcycle maker, plans to build a new breed of off-road machine shaped like a robotic horse. It is called Corleo, and is shaped like a headless steed; a pair of handlebars serves as reins. Like a real horse, the rider will control it with very subtle movements. These will be detected by a combination of sensors, with the data passed on to an AI system that instructs motors to respond accordingly.