One clause of this chapter had a career of its own. The phrase saying that great skill seems clumsy became a standing term in Chinese aesthetic and craft vocabulary, used of calligraphy, painting, poetry and pottery, and it names a quality that later criticism prized very highly: work whose mastery shows as apparent artlessness rather than as visible finish.
The connection to the rest of the book is direct. Chapter twenty-seven had already said that a good traveller leaves no tracks and a good reckoner needs no counting sticks, which is the same claim about the invisibility of competence. What this chapter adds is the appearance term. The expert does not merely leave no trace; the expert positively looks worse than the competent journeyman, because the marks by which skill is usually recognised are the marks of a stage below mastery.
That is a testable claim about a real phenomenon rather than a paradox. Polish, symmetry and evident control are what a maker produces while still demonstrating capability, and they are the first things to go once the maker stops demonstrating.
Two cautions come with the idea, and later Chinese criticism was well aware of both. Deliberate clumsiness is not the thing being described, since a contrived roughness is another kind of display. And the standard cannot be applied from outside, because genuine incompetence and apparent clumsiness look identical to anyone who cannot do the work.
The book itself is a case in point. Its plainness, repetition and refusal to argue are either the marks of a text that has stopped performing or the marks of a disorderly compilation, and readers have taken it both ways.