“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.” (227, Judgment)

“In seduction, hesitation is fatal – it makes your victims conscious of your intentions. The bold move crowns seduction with triumph: It leaves no time for reflection.” (228)

“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 will 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.” (233)

“Boldness directs attention outward and keeps the illusion alive.”

“Audacity separates you from the herd. Boldness gives you presence and makes you seem larger than life. The timid fade into the wallpaper, the bold draw attention, and what draws attention draws power.” (228-229)
 

We cannot keep our eyes off the audacious – we cannot wait to see their next bold move.

 
“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.” (234)

“Boldness should never be the strategy behind all of your actions. It is a tactical instrument, to be used at the right moment. Plan and think ahead, and make the final element the bold move that will bring you success.” (235)

“Timidity has no place in the realm of power; you will often benefit, however, by being able to feign it. At that point, of course, it is no longer timidity but an offensive weapon: You are luring people in with your show of shyness, all the better to pounce on them boldly later.”