Daodejing Chapter 58 breakdown: the sage is pointed but does not pierce

Richard Brown
2 min readSep 1, 2023


Chapter 58 of the Daodejing examines the relationship between governance and the behaviour of the governed, as well as the often-paradoxical nature of fortune and misfortune. Here is a breakdown:

Section 1
When the government is dull and vague,
The people are honest and simple.
When the government is repressive and intrusive,
The people are crafty and cunning.

The opening section of the chapter reprises the same theme of the middle segment of Chapter 57. When the ruler is not overly forceful or intrusive, the people are more genuine and straightforward. When they do not have to deal with excessive regulations or scrutiny, they remain true to their natural state.

Conversely, when a ruler is too controlling and oppressive, the people respond by becoming sly and deceitful. When they have to constantly look behind their back to make sure no one is watching their every move, the people inevitably feel the need to find ways to bypass the system.

Section 2
Fortune is rooted in misfortune.
Misfortune lurks beneath fortune.
Who knows the boundary?
There is no fixed standard.
Right can turn into wrong.
Good can turn into evil.
Man has been puzzled
For a very long time.

The middle section highlights the cyclical nature of fortune and misfortune. Just as good times can lead to complacency and eventual decline, tough times can often be a breeding ground for growth and eventual success. Both states are transient, and one often leads to the other.

Laozi reflects on the unpredictability of life’s experiences and the relativity of our values. What may seem right or good in one context can turn out to be wrong or evil in another. It is a constant struggle to find clarity in an ever-shifting moral landscape driven by rapid cultural, technological, and social changes.

Section 3
In the final section of the chapter, Laozi describes the qualities that a sage possesses to navigate these challenges.

The sage is:
Pointed but does not pierce: He has clarity and purpose without causing harm to others.
Sharp but does not hurt: He is astute and discerning without using his insights to hurt others.
Direct but does not offend: He is candid and straightforward without being rude or abrasive.
Brilliant but does not dazzle: He enlightens with his wisdom without overpowering or blinding others.

Chapter 58 underscores the importance of balance, both in governance and personal behaviour. The Dao is about recognizing and respecting the natural ebb and flow of life, understanding the intricate balance of opposites, and cultivating wisdom that guides others without imposing on them.

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Richard Brown

I live in Taiwan and am interested in exploring what ancient Chinese philosophy can tell us about technology and the rise of modern China.