Law 28: Enter Action With Boldness

If you are unsure of a course of action, do not attempt it. Your doubts and hesitations will infect your execution. Timidity is dangerous: Better to enter with boldness. Any mistakes you commit through audacity are easily corrected with more audacity. Everyone admires the bold; no one honors the timid. – Robert Greene

I am reading Robert Greene’s The 48 Laws of Power [Kindle] for the second time. A selection of his 48 rules are in my personal bible. I’m a strong believer in re-reading and reviewing your favorite content. You always learn something new. Not unlike the way your experience evolves as you appreciate a favorite song or movie.

This time Law 28 really spoke to me. The power of audacity and boldness. Whatever your politics, Trump has it in spades. Softbank founder Masayoshi Son. Of course Elon Musk.

Here’s an excerpt from Law 28: Enter Action With Boldness:

—

Most of us are timid. We want to avoid tension and conflict and we want to be liked by all. We may contemplate a bold action but we rarely bring it to life. We are terrified of the consequences, of what others might think of us, of the hostility we will stir up if we dare go beyond our usual place.

Although we may disguise our timidity as a concern for others, a desire not to hurt or offend them, in fact it is the opposite – we are really self-absorbed, worried about ourselves and how others perceive us. Boldness, on the other hand, is outer-directed, and often makes people feel more at ease, since it is less self-conscious and less repressed.

[…]

Few are born bold. Even Napoleon had to cultivate the habit on the battlefield, where he knew it was a matter of life and death. In social settings he was awkward and timid, but he overcame this and practiced boldness in every part of his life because he saw its tremendous power, how it could literally enlarge a man (even one who, like Napoleon, was in fact conspicuously small). We also see this change in Ivan the Terrible: A harmless boy suddenly transforms himself into a powerful young man who commands authority, simply by pointing a finger and taking bold action.

You must practice and develop your boldness. You will often find uses for it. The best place to begin is often the delicate world of negotiation, particularly those discussions in which you are asked to set your own price. How often we put ourselves down by asking for too little. When Christopher Columbus proposed that the Spanish court finance his voyage to the Americas, he also made the insanely bold demand that he be called “Grand Admiral of the Ocean.” The court agreed. The price he set was the price he received – he demanded to be treated with respect, and so he was. Henry Kissinger too knew that in negotiation, bold demands work better than starting off with piecemeal concessions and trying to meet the other person halfway. Set your value high, and then, as Count Lustig did, set it higher.

Understand: If boldness is not natural, neither is timidity. It is an acquired habit, picked up out of a desire to avoid conflict. If timidity has taken hold of you, then, root it out. Your fears of the consequences of a bold action are way out of proportion to reality, and in fact the consequences of timidity are worse. Your value is lowered and you create a self-fulfilling cycle of doubt and disaster.

Remember: The problems created by an audacious move can be disguised, even remedied, by more and greater audacity.