The Dangerous Art of Asking Questions

Growing up in south Wales, I never accepted what anyone told me at face value. I always wanted to know why. If it rained for days on end — which it frequently seemed to do — I wanted to know what caused it. I wasn’t especially bright. Just incurably curious.

Every age produces one person like that — someone who keeps asking why until everyone else goes home. In fifth-century BCE Athens, that person was Socrates: barefoot, bearded, and constitutionally incapable of leaving a thought alone.

He wandered the city asking awkward questions, irritating important people, and generally behaving like a man who’d never learned the social value of nodding politely and moving on.

The Big Idea

Everyone wants to sound clever. Fewer of us enjoy discovering we’re wrong.

Socrates thought wisdom begins precisely there — in admitting ignorance. Not ignorance as failure, but as an honest starting point. To say I don’t know wasn’t weakness; it was the doorway to understanding.

He believed knowledge and goodness were linked: people do wrong not because they’re wicked, but because they don’t yet see clearly. It’s an unusually generous view of human nature — and possibly the most optimistic thing ever said about politicians.

The Man and the Moment

Socrates was born around 470 BCE, when Athens was loud with confidence. Democracy was new, rhetoric was fashionable, and everyone had an opinion they were keen to share. The city buzzed with art, argument and self-belief.

Into this stepped a man with one cloak, minimal footwear, and an alarming habit of asking what people meant. He’d fought bravely as a soldier, but preferred combat with ideas. His wife Xanthippe, by most accounts, had heard quite enough philosophy before breakfast.

According to legend, his friend Chaerephon asked the Oracle at Delphi whether anyone was wiser than Socrates. The answer: no one. Most people would have framed it. Socrates assumed it must be wrong.

So he set out to test it by questioning those who claimed wisdom — politicians, poets, craftsmen. What he found disturbed him. The politicians confused confidence with competence. (Nothing new there then). The poets couldn’t explain their own work. And the craftsmen assumed expertise in one area meant mastery of all.

Socrates realised he was wiser than them only because he knew what he didn’t know. From that awkward insight, a life’s mission emerged.

The Art of Being Annoying

Each day he went to the agora and started conversations. He asked about justice, courage, love, and gently dismantled every confident answer he was given. People left these exchanges feeling exposed, irritated, and oddly grateful.

His method was simple: ask a question, respond with another, and keep going until something collapses. Today we call it the Socratic method; at the time it felt more like intellectual strip-searching.

Yet people followed him. Not because he flattered them — he didn’t — but because he refused to bluff. Where others sought influence, Socrates sought clarity. He treated thinking as a form of moral hygiene: ignore it for too long and things start to smell.

Why It Mattered

Socrates redirected philosophy from stars and numbers to human life. He cared less about what the universe was made of than about how we should live in it.

He insisted that self-examination mattered more than wealth or reputation. That virtue wasn’t blind obedience but intelligent reflection. That slogans, habits and inherited opinions were poor substitutes for understanding.

Most dangerously, he turned questioning into a moral act. Knowledge, he believed, should make us better, not louder. Ignorance wasn’t the problem; pretending to know was. Does that remind you of anyone?

Athens Loses Its Nerve

For years, Athens tolerated Socrates as a civic nuisance. But after losing a disastrous war with Sparta, the city soured. Confidence curdled into resentment. People wanted certainty, not questions.

Socrates did not adjust his tone.

Some of his former students had disgraced themselves politically, which didn’t help. Eventually, enough powerful Athenians decided the old gadfly had gone too far.

He was charged with impiety and corrupting the youth by effectively, encouraging free thought. A crime that has never gone out of fashion. The trial in 399 BCE was close, but the jury voted for execution.

Socrates could have escaped death by recanting his “crimes,” but he refused. Breaking the law, even unjustly applied, would betray everything he’d taught. He drank hemlock among friends, calmly discussing the soul as the poison crept upward. It was both heroic and faintly theatrical — philosophy’s most famous mic-drop.

The Legacy

Socrates wrote nothing. Plato wrote everything.

Through his students, Socrates became immortal: the man who never stops asking. He lives on in every awkward question, every challenge to authority, every moment when someone says, “But how do we know that?”

His real gift wasn’t cleverness but courage. He showed that thinking could be an act of defiance — and that truth-telling sometimes comes with a price.

The line from him runs through science, journalism, and any discipline that values inquiry over certainty. He remains philosophy’s conscience: a reminder that comfort and honesty rarely share a bed.

In Our Time

If Socrates were alive today, he’d be banned from social media within a week. Platforms built on certainty don’t cope well with questions.

He’d be the man in the café asking strangers what happiness means until the Wi-Fi mysteriously failed. He’d recognise modern sophists instantly — influencers and pundits selling certainty at scale. “You sell answers,” he’d say. “I’m only buying questions.”

Ask him about AI and he’d smile. “It answers quickly,” he’d say. “But does it understand slowly?”

In an age that mistakes noise for wisdom, Socrates feels radical. His method — listen, ask, listen again — is unfashionable to the point of rebellion. He reminds us that disagreement isn’t division; it’s the beginning of thought.

He’d still irritate us. But perhaps that’s the point. Affection for Socrates means gratitude for the person who won’t let us settle for easy answers.

The Essence

“The unexamined life is not worth living.”

He might add: “The unexamined tweet isn’t worth posting.”

Wisdom doesn’t shout. It asks. And sometimes, after a long conversation, it buys the next round.