Cloud of Unknowing - The Path of the Christian Mystic by Paul Siddall

“For I tell you this: one loving, blind desire for God alone is more valuable in itself, more pleasing to God and to the saints, more beneficial to your own growth, and more helpful to your friends, both living and dead, than anything else you could do.”
― Anonymous, The Cloud of Unknowing

The Cloud of Unknowing is an anonymous work of Christian mysticism written in Middle English in the latter half of the 14th century. The text is a spiritual guide on contemplative prayer in the late Middle Ages. The underlying message of this work suggests that the way to know God is to abandon consideration of God's particular activities and attributes, and be courageous enough to surrender one's mind and ego to the realm of "unknowing", at which point one may begin to glimpse the nature of God.
“Let everyone beware lest he presume to take it upon himself to criticize and condemn other men's faults without his having been truly touched within by the Holy Spirit in his work. Otherwise he may very easily err in his judgments. Beware therefore. Judge yourself as seems right to you between yourself and your God, and let other men alone.”
― Ira Progoff, The Cloud of Unknowing
The Cloud of Unknowing, a masterpiece of simplicity that distills a complex mystical epistemology and discipline into engagingly readable prose, embodies a paradox. It offers a method by which the suitably disposed reader may practice an advanced and even austere form of contemplation - the divesting of the mind of all images and concepts through an encounter with a "nothing and a nowhere" that leads to the mysterious and unfathomable being of God Himself. Yet as the account of this exercise unfolds, the genial and hospitable tone of the author humanizes the austerity of the method and persuasively draws the reader into what Evelyn Underhill calls "the loving discernment of Reality" (Sequence, p. 81).

We can begin to understand the meaning of the Cloud by looking at what may be the most famous quotation in Western mysticism, the passage in the Confessions, IX, 10, where Augustine muses upon the ecstasy at Ostia, an experience that he had in a final conversation with his mother, Monica (McGinn, p. 234). By its similarities and contrasts with the ideas of The Cloud of Unknowing, this brief classical statement of the contemplative ascent can introduce us to the whole mystical tradition:

If to any man the tumult of the flesh grew silent, silent the images of earth and sea and air: and if the heavens grew silent, and the very soul grew silent to herself and by not thinking of self mounted beyond self: if all dreams and imagined visions grew silent, and every tongue and every sign and whatsoever is transient - for indeed if any man could hear them, he should hear them saying with one voice: We did not make ourselves, but He made us who abides forever: but if, having uttered this and so set us to listening to Him who made them, they all grew silent, and in their silence He alone spoke to us, not by them but by Himself: so that we should hear His word, not by any tongue of flesh nor the voice of an angel nor the sound of thunder nor in the darkness of a parable, but that we should hear Himself whom in all these things we love, should hear Himself and not them: just as we two had but now reached forth and in a flash of the mind attained to touch the eternal Wisdom which abides over all: and if this could continue, and all other visions so different be quite taken away, and this one should so ravish and absorb and wrap the beholder in inward joys that his life should eternally be such as that one moment of understanding for which we had been sighing - would not this be: Enter Thou into the joy of Thy Lord? (Confessions, trans. Sheed, pp. 200-01).

What is striking about this passage is the combination of two movements: a sweeping review of nature, human psychology, and the world of signs, followed by the "silencing" or negation of everything that is not God. These two movements present us with affirmation and negation; or, in terms more proper to mystical discourse, with the kataphatic and apophatic phases of the mystical ascent. Moreover, the passage from Augustine, which is richly affirmative, is a fine example of illumination and union, which, together with purgation, are the mystic's three traditional types of experience. The Cloud of Unknowing, by contrast, is essentially apophatic in its emphasis and focuses almost entirely on the "silencing" described by Augustine: it collapses the meditation on nature to brief allusion, and discusses the soul's activities only in the most practical manner. Perhaps most important, whereas Augustine refers to "that one moment of understanding" (intelligentia), the method of the Cloud emphasizes the movement described earlier when, as all things grew silent, "the very soul grew silent to herself and by not thinking of self mounted beyond self."