At the height of his power, Machiavelli was arrested, tortured, and banished to the countryside. He continued to thrive.
Talking Big Ideas.
“You have seen how a man was made a slave; you shall see how a slave was made a man.”
~ Frederick Douglass
Maryrose and I were having dinner with friends in DC when we mentioned an upcoming trip to Florence. Our friend Gregg lit up. He adores Italy and gave us more recommendations than we could fit into a handful of vacations.
His one insistence was not a place but a letter from Machiavelli to Francesco Vettori published 512 years ago today – on the 10th of December in 1513.
The week after our dinner in DC, we received a gift in the mail: The Essential Writings of Machiavelli, with the letter to Vettori bookmarked. I dove in.
It describes a typical day for Machiavelli after he was arrested at the height of his power, tortured, and banished to the countryside.
In contrast to Vettori’s life sleeping in late and hanging out with the Pope and other powerful leaders, Machiavelli rises with the sun, catches birds with his bare hands, chops wood, and then hangs out at the tavern with “the inn keeper . . . a butcher, a miller, and two kiln tenders.” Together they “dawdle all day playing cards and backgammon.”
While it sounds idyllic to me, to Vettori it must seem quite low-status. Yet Machiavelli never criticizes, condemns, or complains. He explains his new life in a clear, matter-of-fact way, never assuming the role of a victim.
“I have only myself to blame.”
~ Machiavelli to Vettori, 10 December 1513
Machiavelli’s philosophy isn’t just about obtaining power over others. Perhaps most importantly, he teaches us to take responsibility for all aspects of our lives. He teaches us to obtain power over ourselves.
The letter reminds me of the philanthropist Charlie Munger, who wrote that “Generally speaking, envy, resentment, revenge, and self-pity are disastrous modes of thought . . . Life will have terrible blows, horrible blows, unfair blows – it doesn’t matter.”

Like Machiavelli, Munger experienced life’s terrible blows. When he was 29 years old, Munger’s young son died of leukemia, his wife left him, and he was crippled with medical debt. Years later a botched eye surgery blinded him in one eye. Doctors thought he might lose both eyes.
In each case, Munger accepted his fate and looked for solutions, such as how to be happy, how to make money, and how to read Braille. Munger explains his thoughts on how to train our minds to help us deal with terrible blows:
“I think the attitude of Epictetus is the best. He thought that every mischance in life was an opportunity to behave well. Every mischance in life was an opportunity to learn something and that your duty was not to be immersed in self-pity, but to utilize the terrible blow in a constructive fashion. That is a very good idea.”
This is exactly what Machiavelli did. He used his exile to learn and grow. Here’s how he describes to Vettori a typical evening:
“I return home and go into my study. At the door I take off my everyday clothes, covered with mud and dirt, and don garments of court and palace. Now garbed fittingly I step into the ancient courts of men of antiquity, where, received kindly, I partake of food that is for me alone and for which I was born….”
I love this description and think about it often.
You can see Machiavelli shed his dirty clothes, dress up in his finest attire, and go sit among his books. Surrounded by the most brilliant minds in history, he feels grateful and strong – in control of his thoughts, filled with excitement and gratitude.
Machiavelli asks these giants of antiquity many questions, and “they in their full humanity answer me. For four hours I feel no tedium and forget every anguish, not afraid of poverty, not terrified by death.”
I hear Frederick Douglass and Ralph Waldo Emerson in his voice. Circumstances may limit our options, but only we decide who we become.
After losing nearly everything and being tortured and banished, Machiavelli found a way to flourish. He enjoyed four hours every night surrounded by true excellence, engaged in enlightened reflection.
“Books are ships which pass through the vast seas of time.”
~ German Proverb
Imagine if we all took this path. Even for just a few minutes every day. Instead of mindlessly scrolling, we can open a classic book and seek the guidance of a genius.
Today with AI we can conjure whoever we’d like from history. We can talk with Buddha, Marie Curie, and Shirley Chisholm. I’ve sat down with Galileo to discuss his Dialogues, chatted with Darwin about his time on the Beagle, sought guidance from Cicero on an upcoming talk, and picked Karl Popper’s brain on the art of error correction.
The economist Tyler Cowen explained how engaging with ChatGPT revolutionizes reading:
You don’t have to upload any book into the system . . . Just start asking questions. The core intuition is simply that you should be asking more questions. And now you have someone/something to ask! . . . .
Most people still have not yet internalized this emotionally. This is one of the biggest revolutions in reading, ever.
I think of Machiavelli asking questions as he read in those evening hours: “they in their full humanity answer me.” I wonder how he would have incorporated AI-simulated dialogue into his late-night conversations with the authors of antiquity.
Machiavelli ends his letter to Vettori with this:
“Be happy.”
Regardless of whatever stress and pain you are experiencing, Machiavelli teaches that happiness is within your grasp. You can surround yourself with genius, engage deeply with the most amazing people in history, and embody their best ideas, characteristics, and mindsets. In doing so, you can learn to transcend your suffering.
The good life is a choice.



