Law 28: Enter Action With Boldness

The 48 Laws Of Power Summary Series


“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.”

When you enter with boldness you are going on the aggressive. You’re playing offence instead of defense. This may be one of the most important laws for young men and women of our generation because a lot of them are soft, entitled and undisciplined. Most of us who have grown up in the “western world” have been extremely privileged with the abundance of resources we have free easy access to. The majority of us have not experienced any wars, economic collapses or extreme suffering. I reflect on my younger self with disappointment at how soft I was. Only for the last couple of years have I been actively attempting to mitigate this tendency. Hopefully this piece can assist you in that process as well.

Consistently backing down and retreating in the face of confrontation or challenge gives the aggressor autonomy and power over you. Recognize if you possess the habit of retreating and compromising as other’s walk all over you. You can learn the hard way like I did, or you can embody the lesson contained here and start living it.

Think of an athlete you admire, if they enter that game with anything less than total confidence in themselves and their team, than they’ve already given their opponent the advantage. You can see it in a person’s eye’s and body language.

We live in a time right now where it’s never been easier to run and create your own business and lead the life of an an entrepreneur, the following quote applies to that life.

“Great enterprises are only achieved by adventurous spirits, they who calculate with too great nicety every difficulty and obstacle which is likely to lie in their way, lose that time in hesitation which the more daring seize and render available to the loftiest purposes.”

Many of us spend great amounts of time planning even the most minute and insignificant tasks in order to chase the impossible pursuit of pefection. More often than not it’s wiser to move forward with any decision, rather than hesitate on no decision.

“On the plains of hesitation lay the bleached bones of countless millions who, at the dawn of decision, sat down to wait, and in waiting died.” — Sam Ewing

Execution is everything.

The Story Of Huh Saeng

In a lowly thatched cottage in the Namsan Valley there lived a poor couple, Mr. and Mrs. Huh Saeng. The husband confined himself for seven years and only read books in his cold room…. One day his wife, all in tears, said to him: “Look here, my good man! What is the use of all your book reading? I have spent my youth in washing and sewing for other people and yet I have no spare jacket or skirt to wear and I have had no food to eat during the past three days. I am hungry and cold. I can stand it no more!” … Hearing these words, the middle-aged scholar closed his book… rose to his feet and… without saying another word, he went out of doors…. Arriving in the heart of the city, he stopped a passing gentleman.

Namsan Valley

“Hello, my friend! Who is the richest man in town?”

“Poor countryman! Don’t you know Byôn-ssi, the millionaire?

His glittering tile-roofed house pierced by twelve gates is just over there.”

Huh Saeng bent “his steps to the rich man’s house. Having entered the big gate, he flung the guest-room door open and addressed the host:

“I need 10,000 yang for capital for my commercial business and I want you to lend me the money.”

“Alright, sir. Where shall I send the money?”

“To the Ansông Market in care of a commission merchant.”

“Very well. sir. I will draw on Kim, who does the biggest commission business in the Ansông Market. You’ll get the money there.”

“Good-bye. sir.”

When Huh Saeng was gone, all the other guests in the room asked Byôn-ssi why he gave so much money to a beggarlike stranger whose family name was unknown to him. But the rich man replied with a triumphant face:

“Even though he was in ragged clothes, he spoke clearly to the point without betraying shame or inferiority, unlike common people who want to borrow money for a bad debt. Such a man as he is either mad or self-confident in doing business. But judging from his dauntless eyes and booming voice he is an uncommon man with a superhuman brain, worthy of my trust. “I know money and I know men. Money often makes a man small, but a man like him makes big money. I am only glad to have helped a big man do big business.”

Behind The Scenes Of Royal Palaces In Korea, Ha Tae-Hung, 1983.

When asking for something, many often approach with an air of timidity. Huh Saeng entered with such audacity and confidence he caught everyone off guard and got exactly what he came for. This story is not included so you can go out and start asking for money from strangers in the hope they say yes. It’s here to show you that directing your boldness and audacity into something your chasing can dramatically increase your likelihood of attaining it.

Keys To Power

“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.”

“Casanova’s boldness was not revealed in a a daring approach to the women he desired, or in intrepid words to flatter her; it consisted in his ability to surrender himself to her completely and to make her believe he would do anything for her, even risk his life, which in fact he sometimes did. The women on whom he lavished this attention understood that he held nothing back from her. This was infinitely more flattering than compliments. At no point during the seduction would he show hesitation or doubt, simply because he never felt it”

Timidity and awkwardness are never celebrated. The who one enters with boldness and courage always wins.

“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.”



Just like any emotion, boldness and audacity must be willfully controlled. It must not control you like a horse controlling it’s rider. You must control the horse. You must control your emotions. Pick your moments.

“To go through life armed only with audacity would be tiring and also fatal. You would offend too many people as it is proven by those who cannot control their baldness…Timidity has no place in the realm of power.”

If you took value from this piece consider hitting the ❤ button . If you would like to receive these writings directly in your inbox you can subscribe here.

Originally Posted

Self reflective writings & book summaries on philosophy, psychology and human behaviour.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store