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 resolution. 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. [...] Hesitation puts obstacles in your path, boldness eliminates them. [...] 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. [...] Few are born bold. [...] You must practice and develop your boldness. [...] To go through life armed only with boldness you would offend too many people."
Robert Greene, The 48 Laws of Power
Robert Greene’s The 48 Laws of Power was a memorable read because of quotes like these.
The bold are envied, at least I have noticed, in many areas of life. As Green notes, this is certainly the case in seduction. Boldness is synonymous with confidence, and who doesn’t need more of that?
The want to look at the first sentence. “If you are unsure of a course of action, do not attempt it.” This would be the case the majority of the time, I would think. I have observed my own timid actions, or thoughts, and cursed myself later for not committing to them fully. If you are lucky, maybe your cautions can be resolved before the action is started, but if not I agree that it would be better to not attempt them. So then, how does someone who is overly analytical do anything? I feel this way, at times, that there is always some other way to analyze a course of action. The answer is discussed by Greene later and also included in the following notes. It is;
“Few are born bold. […] You must practice and develop your boldness.”
Test the boldness in your actions by estimating the amount of uncertainty that is involved. Resolve to enter with boldness and then play it the best you can as new information arises. This is the case with so many heart-pounding moments in recent memory. Like;
- asking a girl out
- attempting a jiu jitsu move
- getting up on stage for stand up comedy
- hitting a golf shot
There are a lot of questions you can ask that you won’t know the answer to until after the first action is taken: “What if she doesn’t look interested?” “What if he sees it coming?” “What if no one laughs?” “What if the balls ends up in the creek on the right?”
The majority of the time, the uncertainty will disappear in the moment if  the first action is entered with boldness, and  you practice being ‘’in the arena’’.
Being “in the arena” is a reference to Steven Pressfield’s War of Art. He references a story of when a critic gave a brutal review of something he created. One of his friends—mentor, maybe—told him something along the lines of, “You took a few punches. So what? That’s the price you pay for being in the arena.” It would seem wise to be the bold actor in the arena and not the timid one.
I love that Green added the caveat, “To go through life armed only with boldness you would offend too many people.” Obviously important, but worth explicitly referencing here at the end.