I doubt that the author of The Cloud of Unknowing came to the deepest non-state states of consciousness. The text itself reveals some fundamental anxieties as well as an inadequate “map” of the “territory” beyond “the cloud of unknowing.”

Let me start with the latter. The Cloud author illuminatingly distinguishes between “the cloud of forgetting” and “the cloud of unknowing.” The first cloud is basically a rigorous process of letting go all that is not God in himself, God’s “bare existence.” That is a great piece of negative theology. The second cloud is an apt metaphor for a state that Zen calls samadhi: there is neither the mental sense nor the physical sense activated. Initially, this thought-free or almost thought-free state ‘feels like’ almost nothing. It seems neutral, colorless, perhaps even bland. Rightly, this is a “cloud of unknowing” in the sense of jettisoning all forms of human knowing.

The Cloud author is on the right track, and I like the topographical hints he provides. And yet, my own experience as well as profound sacred texts like The Upanishads both reveal that there is far more to the story, as it were. Based on my reading of The Cloud of Unknowing, the author may have gotten ‘stuck’ at that ‘location.’ This is why, in some traditions, a teacher or guru is helpful: for he or she can point us beyond this state, and grace may be bestowed upon us.

Perhaps the bigger clue to The Cloud author’s stickiness is the fact that he has too many bones to pick. As Chuang Tsu says, “Those who argue miss the point.” And The Cloud author is too caught up in ‘making a case’ for the contemplative life (Mary) over the active life (Martha). A number of chapters are devoted to pushing back against those real and imagined critics of the supremacy of the Christian mystical path. Clearly, one who is more settled would feel no compunction to make such a case, and certainly not at such great length, for he would have found, and abided in, the peace that surpasses all understanding.

Additionally, The Cloud author goes on at considerable length about all the fakers, feigners, and hypocrites, all those capable to posing as contemplatives without actually having “gone there.” Fair enough. In fact, the student needs to see the traps into which he may fall, and Zen master Boshan, in his “Exhortations for Those who Arouse the Great Doubt,” also exposes different kinds of Zen wannabes. Yet Boshan, unlike The Cloud author, doesn’t get infatuated by the topic (or by the cleverness of his tongue), and one can tell that he has the interest of his monks, who are seeking the Great Way, at heart. I can’t say the same about The Cloud author. My sense is that he still felt threatened by posers, and that, if true, only goes to show that he hadn’t carried the existential inquiry far enough.

For surely, when that existential inquiry is carried through to the end, then there is a deep relaxation throughout all of one’s being, a relaxation intermingled with compassion. It is like a deep and steady softening.