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At the end of Chapter 23 you read, “What is the Machiavellian alternative to a big ego? Not humility, that’s for sure.” Read about the Machiavellian version of Confidence.

What About Humility? - Don’t be too humble or too proud. We recommend the middle ground. Pretend to be humble.




Confidence in yourself is essential to your success. I’m sure we can all agree with that statement, but we need to think about what it means. The word itself means “with (con) faith or trust (fidere).” Self-confidence means “with faith or trust in oneself.”

The Machiavellian perspective is a way of thinking and acting in the World. It recommends that:

  • You should go boldly about the business of building a life for yourself.
  • You should define your own goals in life
  • You should develop a reasonable plan for achieving those goals
  • You should pursue your goals by energetically implementing your plan
  • You should not be stopped by failure or bad luck. Deal with the problem and move on.
  • If your plan is not working, devise a better plan.
  • All the while, you should be building yourself into the person you desire to be. Be supple and flexible. Incorporate new behaviors into your repertoire of behaviors as needed. Grow and change as you need to.
  • Live long.
  • Prosper.

You are your own tool for building a life. Make yourself into a person in whom you have confidence. Assess your strengths and weaknesses. Develop the strengths. Eliminate the weaknesses. Remember that you learn what you do. You can read a book on the history of the bicycle if you want to learn history. But if you want to learn to ride a bicycle, you have to ride a bicycle. If you want to live your life, you have to grasp the handlebars of life, sit on the seat, and start pedaling.


Machiavelli himself wrote a great deal about the training of an army. On one occasion he wished to display his advanced knowledge of military formations. With the permission of the commander of the army, Machiavelli started shouting orders to the troops on the drill field so as to form them up in a battle formation. The troops, no doubt with great amusement, followed his orders to the letter, resulting in total confusion, troops marching into walls, into each other, and in random directions. After giving Machiavelli time to make a complete fool of himself, the experienced commander started shouting orders and in only a few minutes every soldier was standing in perfect formation with weapons ready to confront the enemy. Machiavelli had taught himself how to write a great chapter, but not how to put an army into formation for battle. The experienced commander had learned how to handle troops, but was probably not so skilled as an author. You learn what you do.


Confidence is not blind faith that things will turn out well. Confidence is not repeating over and over to yourself “I think I can. I think I can. I think I can. ...” Confidence is built by doing the best you can to implement your plan for your life. Develop the skills you need by doing the things you need to. If something doesn’t turn out well because you lacked a skill, then develop that skill some more and try it again. Or hire someone to perform that task for you. Or figure out a way to accomplish the same goal without that skill. Use your brain and the brains of those around you to figure out the best methods for dealing with the situations that confront you.





Here is everything you need to know about humility and modesty.

  • No one likes a braggart. People should become aware of your accomplishments without you tooting your own horn too loudly or too obviously. Braggarts are seen as insecure assholes.
  • Make the normal expressions of modesty in all situations without overdoing it. “Humbler than thou” is almost as annoying as “Holier than thou.”
  • Self-deprecating humor is usually appreciated. Those who make jokes about their own mistakes are seen by others as confident and capable.
  • Admitting that you are wrong or have made a mistake is normally seen by others as strength of character. And it sets an example for others around you to follow. Be capable of apologizing for your mistake to those who were inconvenienced by it. Tell them in detail how you will prevent a similar problem from occurring in the future.

That’s everything.


Chapter 23





Download or read online: Machiavelli’s Prince in English translation by W. K. Rowling


Read a brief summary of Machiavelli’s life and works,

written by W. K. Rowling as the Introduction to his translation of The Prince


A readable summary of Machiavelli’s Prince can be found at






The Modern Prince:

Better Living Through Machiavellianism


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