The Short of It:
It’s the how, not the who.
15. the manifestation of virtue.
The skilful philosophers that were in the olden time had a mystic communication with the abysses. They were deep and cannot be known. And whereas they cannot be known, I strain my imagination to picture them. Timid were they, like one fording a stream in winter. Cautious were they, like one who dreads his neighbour. Circumspect were they, like a [person] from home. Vanishing were they, like ice that is about to melt. Simple were they, like unwrought wood. Vacant were they, like a valley. Dim were they, like muddy water.
Who is there that can take the turbid water, and, by stillness, make it gradually alive?
Those who keep this Tau desire not fulness. And whereas they are empty, they may wax old, and yet not stand in need of renewing.
15. ‘the exhibition of the quality.’
15.1 The skilful masters (of the Tao) in old times, with a subtle and exquisite penetration, comprehended its mysteries, and were deep (also) so as to elude [people’s] knowledge. As they were thus beyond [people’s] knowledge, I will make an effort to describe of what sort they appeared to be.
15.2 Shrinking looked they like those who wade through a stream in winter; irresolute like those who are afraid of all around them; grave like a guest (in awe of [their] host); evanescent like ice that is melting away; unpretentious like wood that has not been fashioned into anything; vacant like a valley, and dull like muddy water.
15.3 Who can (make) the muddy water (clear)? Let it be still, and it will gradually become clear. Who can secure the condition of rest? Let movement go on, and the condition of rest will gradually arise.
15.4 They who preserve this method of the Tao do not wish to be full (of themselves). It is through their not being full of themselves that they can afford to seem worn and not appear new and complete.
15. the revealers of virtue.
15.1 Those of yore who have succeeded in becoming masters are subtile, spiritual, profound, and penetrating. On account of their profundity they can not be understood, therefore I endeavor to make them intelligible.
15.2 How cautious they are! Like [people] in winter crossing a river. How reluctant! Like [people] fearing in the four quarters their neighbors. How reserved! They behave like guests. How elusive! They resemble ice when melting. How simple! They resemble rough wood. How empty! They resemble the valley. How obscure! They resemble troubled waters.
15.3 Who by quieting can gradually render muddy waters clear? Who by stirring can gradually quicken the still?
15.4 [Those] who [cherish] this Reason [are] not anxious to be filled. Since [they are] not filled, therefore [they] may grow old; without renewal [they are] complete.
The Long Of It:
The specifics of the ancient masters are less important than the details of today.
Life is a paradox we must embrace for survival (both individually and societally): careful when crossing a river in winter (but still brave enough to cross); tentative of everyone (but not cowards); reserved and polite (but anxious to appear); slow to act (but steadily acting); simple in nature (but complex in possibility); empty like the valley (which allows for growth); and dirty like muddy water (but steadily cleansing).
-TB