Michel de Montaigne (1533-1592) lived in dangerous times, but he adopted suitable countermeasures. He protected himself and his family by steering away from honours and competition that could have easily turned sour. He assessed the risks, kept his eyes open, and did overall much better than his peers.

The Renaissance was a period of open-mindedness coupled to intellectual progress. Montaigne favoured inquiry and wrote against prejudice, but did not fool himself about human nature. He knew how hard it is for people to abandon superstition.

Montaigne proved a master at navigating difficult times. He conveyed his criticism indirectly by presenting it as historical or literary commentary. He talked to people in both camps, that is, Catholics and Protestants, which represented the two sides of the political spectrum in the sixteenth century.

I call Montaigne’s strategy “calibrated daring.” There was a master in this discipline also in Italy. He was one generation younger than Montaigne. I am referring to Count Baldassare Castiglione (1478-1529), whose best-known achievement is to have writing “The Book of the Courtier.”

While Montaigne is focusing on self-reliance and happiness as life goals, Castiglione devoted his literary efforts to describe the qualities and conduct expected of a gentleman. His book emphasizes diplomacy, eloquence, courage and intelligence.

The education received by Castiglione was better than the one received by Montaigne. Castiglione was able to read the Greek classics in their original language. He also had access to libraries much wider than Montaigne’s.

Montaigne and Baldassare Castiglione in the Renaissance

While Montaigne spent his professional life working as a lawyer in Bordeaux, Castiglione worked mainly as a diplomat. First, he was employed by the Duke of Milan, Ludovico Sforza (1451-1508), and later by the Marquis of Mantua, Francesco Gonzaga, and the Duke of Urbino, Francesco Maria Rovere.

Montaigne wrote his essays in his farmhouse in the south of France, and Castiglione composed “The Book of the Courtier” in his retirement. Both men arrived at the same conclusion: It’s ethically necessary and mandatory for happiness to be daring, but do not commit suicide by trying to do the impossible.

I regard Castiglione as more experienced than Montaigne in matters of politics and war. He served in high positions where the death was the price to pay for severe mistakes. He saw with his own eyes the rise and demise of many a Duke and Marquis.

Both Montaigne and Castiglione defined accomplishment as “effortless grace,” which combines knowledge, empathy and a high level of alertness. I regard the term “effortless graces” as a synonym to “unconscious competence.” It is the result of long experience and extensive reading.

At the height of his career, Castiglione became himself the ideal Renaissance gentleman. Pope Clement VII (1478-1534) appointed him Ambassador to Spain with the job of finding an an agreement with Emperor Charles V to prevent war. Also in Spain, Castiglione was admired by his balance between daring and diplomacy.

Montaigne and Thomas More in the Renaissance

Not everyone shared the approach taken by Castiglione and Montaigne. During the Renaissance, other men adopted radical positions when those were suicidal. In practically all cases, the result was catastrophic.

Thomas More (1478-1535) worked long years as a lawyer, magistrate and royal servant. He authored philosophical fiction (a book titled “Utopia”) and devoted his evenings to reading the classics. He was also a close friend of Desiderius Erasmus’ (1466-1536) and a member of the English parliament.

Montaigne had opted for steering away from political jobs, considering too dangerous in times of turmoil. You could wake up one day and find yourself on the wrong side of history.

More did exactly the opposite. He seized all opportunities to advance his carrier under King Henry VIII (1491-1547), even if he could not have missed the severe character flaws in the king’s personality. More must have known that he was playing with fire.

Montaigne knew that daring, even calibrated daring, is no longer possible once you have accepted too many constraints. More should have know better, but fell into the trap.

More said no when he was asked for help in annulling the king’s marriage to Catherine of Aragon to marry Anne Boleyn, and declaring the king Head of the Church of England. After a short back-and-forth, the king had More arrested, prosecuted, and sentenced to death.

The movie “A man for all seasons” portrays More as a man of unbreachable integrity, but did his daring change anything? I wonder if he should not have resigned earlier in his career and retire to a farmhouse, just like Montaigne.

Eventually, More was canonized by the Catholic Church in 1935, but his death renders his philosophical fiction “Utopia” even more unrealistic. Since I abhor pointless deaths, More’s biography makes me wonder whether daring is worth anything without calibration.

The Renaissance gives us diametrically opposed examples: Montaigne and Castiglione on one hand, and More on the other hand. These men embody opposite views on daring. Each of us must, with our own behaviour, endorse one or the other view.

I personally endorse peacefulness and tolerance, hoping to learn from history how to prevent conflicts before they occur. I regard the Renaissance as an endless source of wisdom, which can help us build a better future.

If you are interested in putting rational philosophy into daily practice, I recommend you my book titled “The philosophy of builders.”