12. Of Boldness

It’s a simple lesson, one taught in schools, but it holds wisdom for anyone aiming to succeed. Someone once asked Demosthenes, the great Athenian orator, what the most important quality of a speaker was. His answer? Action. And the second most important? Action. And the third? Action. This was a man who knew the craft inside and out, yet he himself wasn’t naturally gifted in this area. It’s strange to think that something as outward and performative as action—more like the skill of an actor than a thinker—could outrank the deeper skills of creativity, eloquence, and reasoning. But there’s a simple explanation: people are more often swayed by appearances than substance. Most humans act more like fools than sages, and it’s the foolish part of us that action appeals to most powerfully.

The same is true of boldness in business and life. What matters most? Boldness. What comes next? Boldness. And after that? You guessed it—boldness. Yet boldness, for all its power, is born of ignorance and arrogance. It’s far less admirable than qualities like wisdom, insight, or skill. Still, boldness has a magnetic pull. It can overwhelm those who lack judgment or courage—which, let’s face it, is most people. Even the wise can be influenced by boldness in their weaker moments. That’s why boldness has shaped revolutions and popular movements, though it tends to fare poorly in the measured, deliberative spaces of governments and courts. Boldness often shines brightest in the beginning, when its energy can create dramatic first impressions. But it rarely delivers on its promises over time.

Boldness is like a fake doctor—someone who brags about amazing cures but doesn’t have the real knowledge to back it up. These “political fakes” might get lucky a few times and pull off impressive wins, but they don’t have the skill to handle long-term challenges. They remind me of the story about Mahomet (Muhammad): he told his followers he would summon a mountain to come to him so he could pray from its peak. When the mountain didn’t move, he calmly declared, “If the mountain won’t come to Mahomet, Mahomet will go to the mountain.” In the same way, a bold person can fail spectacularly and yet brush it off with the same audacity that won people over in the first place. They simply adjust their story and keep going as if nothing happened.

For those with clear judgment, watching bold people can be entertaining—a kind of live comedy. Boldness often flirts with absurdity, and absurdity always invites laughter. Even the average person finds something ridiculous about boldness, especially when it falters. When a bold person is embarrassed, their composure stiffens like a frozen chessboard in a stalemate—not defeated, but unable to make a move. That’s a sight worth noting, though it’s more fit for satire than serious reflection.

One thing is certain: boldness is blind. It doesn’t see the risks, pitfalls, or consequences ahead. This makes boldness a poor guide in planning but a powerful force in action. The best use of bold people is to have them execute plans, not design them. Let them act under the guidance of calmer, wiser minds. In strategy, it’s essential to foresee dangers. In execution, it’s sometimes better not to see them at all—unless they’re unavoidable. Boldness can be a tremendous tool, but only when wielded with care and under control.

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