Contemplating Wisdom: Most Notably, Questions To And For Wisdom


What are some of the questions to which wisdom is the answer?

1.) At what does (my) life ultimately aim? 

A world-class athlete aims at victory, but victory is not wisdom. A business leader aims at success, but success is not wisdom. Neither have yet made the question of wisdom their foregoing concern. For undeniably this question–at what does life ultimately aim?–is a question of wisdom. It’s a question of wisdom as well as a question posed to wisdom. In this sense, it is a potent question for wisdom is what ‘takes up the question’ and wisdom is the answer to this question.

2.) I’m lost, or turned about. I can’t seem to find my bearings. I don’t have a sense of direction. How shall I find my way? 

Wisdom, I suggest, is not actually concerned with how questions. In the ‘eyes’ of wisdom, all how questions are really why or what questions. And, in fact, all why questions are reducible to what questions. The question here is essentially this one: what is it to find my way? What is to be found? Or even: what is it that I truly seek? 

A sense of direction is not a sufficient answer. For, again, what do I seek? To truly seek is to begin to set foot on some path, and that path is what provides me with a sense of direction.

But why isn’t wisdom concerned with why questions? It is, but each why is really a what. In this sense: if I ask, “Why am I living?,” I’m really asking, “What is it that is most essentially worth living for?” 

3.) I don’t know how to live my life. How do I?

Again, not a question of how specifically, for each how is just a reason to find a consultant, an advisor, a coach, or a therapist. To open oneself to the question of wisdom is to feel oneself splayed open and, in the proper sense, tenderized or vulnerable. 

Thus, the question can be reformulated: “What is that life that I long to live for?”

4.) I’m having an existential crisis. What is this?

Exactly. “What is happening?” is, at the broadest level, a question of wisdom.

5.) Something seems off or missing; I feel incomplete somehow. What is it that would make me whole or that would return me to wholeness?

Great question. The key word is “somehow.” A sense that life is mysterious is somehow bound up with the path of wisdom. And if wisdom is anything, it must be in conversation with wholeness. Is not a wiseman a whole? Is he not, in fact, the whole?

Wisdom leaves nothing out. It does not rest until it can rest in, and as, the whole from which or out of which it can bound forth in spontaneous or deliberate action. Wisdom leaps out of the whole without ever leaping away from the whole. 

But why does wisdom leap? Because awakening is the abiding in stillness while wisdom is the stillness-in-action. We don’t call someone wise unless we can see ‘the proof in the pudding.’ No wiseman has ever ‘sat on his hands.’ And yet, no wiseman was ever in a hurry. He is like the stillest water beneath the undulating waves: his actions are these rhythmical waves while his ‘being’ is this stillness, or composure, or boundless, stunningly quiet peace. 

Shared wisdom is peace in knowing of the kind that is, and can only be, experienced together.

Test Piece

I read this tweet fairly recently:

Crafting a social public persona is a prison. Best to face and deal with the pain, shame, and inadequacy that necessitates the creation of a social mask. The resulting authenticity and emergence of our true inner gifts, is infinitely more effective than a curated image anyhow.

Let us grant all these points. I have no truck with them, no objection. But is the one one who tweeted this wise? I don’t know, and I’m not sure that any of us could know simply by reading the above. But why is that? Quite clearly because we don’t yet know how he lives, how he conducts himself. What is his “inner landscape” actually like? Matthew puts it well: “Ye shall know them [i.e., true Christians] by their fruits.” Exactly! And those fruits are not “one-off deeds” like charity on Wednesday. Far from it. A true Christian would radiate with “that peace that surpasseth all understanding,” and thus a wise Christian would necessarily be a loving Christian. 

We cannot do much with what is written alone for the express reason that what is written alone cannot tell us anything substantive about the true source of that writing. Whereas when Jesus says, also in Matthew, “But I say unto you, That ye resist not evil: but whosoever shall smite thee on thy right cheek, turn to him the other also,” dang somehow we know that he’s living what he says. In other words, what he is saying, right here, actually comes directly out of his living truth (or better: Living Truth). There is, quite simply, no doubt about it. 

Of course, we say, “Yes, because the wiseman doesn’t just ‘talk the talk’; he must ‘walk the walk.’” Well, sure, if we can pardon the cliche. But we need to be clear: the wiseman or a wise people walk the talk in a way that fully suggests, without even a shred of doubt, that they have fully integrated that walking talk into every fiber of their being.

Socrates was right: wisdom is an extremely high standard.

Where No Questions Can Arise

Quite often Sri Ramana Maharshi tells a disciple or visitor something like the following: “Only see your true nature and that question will not arise.”

While reading Talks with Sri Ramana Maharshi with sensitivity, one is frequently struck by the aching anxiety as well as the lurching desire behind the questions. It’s as if the mind, arising in the form of thought, were continuing its agitation in the mode of questioning. The satisfaction that seems unfindable is revealed in the question, here and now. Seeing and experiencing this, one can’t but feel a dull ache and a sense of compassion.

To the questioner caught up in misery, Maharshi’s answers or smiles or silence can seem all too inadequate. “Is that all? Just be silent? Just be as you are.” Or: “just inquire into who is asking the question? What do you mean: find out who that is and all will be well?”

I find myself particularly moved by Maharshi’s brightness, quietness, and compassion. Here is loving awareness seeing that all are already realized and could be other than realized. Here is a penetrating vision of the clarity and purity that is right, always right, beneath the struggle and the strife. Here, in a way, is beauty.

Fundamental Anxieties And Spiritual Limitations In The Cloud Of Unknowing

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.

‘Humble Stirrings Of Love’ And ‘Nagging Undercurrents of Doubt’

The Cloud of Unknowing is a hybrid text. For starters, The Cloud author draws heavily on negative theology. This much is abundantly clear in his translation The Mystical Theology of St. Denis. For instance, in Chapter 4, we are to begin by “remov[ing] from God that which is without substance and everything that does not exist” (The Mystical Theology of St. Denis in The Cloud of Unknowing and Other Works, trans. and ed. A.C. Spearing, p. 8). The process of removing this attribute and that from God is textbook via negativa.

The Cloud of Unknowing is clearly very much inspired by this approach, as everything that is not God in himself is to be placed in the “cloud of forgetting” and as “the cloud of unknowing” is indeed the undoing of all knowledge concerned with God’s attributes (and not his “bare existence”), with the intellect, and with the “bodily senses.” All this must go.

And yet, The Cloud author swerves from this strict “jnana path” by claiming, time and again, that it is not the intellect that can reach these heights; instead, it must be “the humble stirring of love.” In this sense, while the outer container of The Cloud is negative theology in the form of intellectual negation (cf. neti neti), the inner substance is eros, an ascent–assisted by and ultimately determined by the Creator–to God himself. This hybrid character is what, by my lights, makes the text so fascinating.

Now to my criticism. I think The Cloud author is so committed to draping all knowledge paths in pride that he’s unwilling to even argue for the need to place love before knowledge. Each time he mentions the inadequacy of the intellect he does no more than posit this, as if it were self-evident. Equally self-evident, he thinks, is that the faculty of the will, via eros love, must point the way (until divine grace can welcome one home).

This is myopia, to be sure. Consider, in this connection, a clear exposition of the huatou in Stuart Lachs’ essay, “Hua-t’ou: A Method of Zen Meditation.” Like self-inquiry, the huatou is very much guided by deep, earnest inquisitiveness. Lachs puts the attitudinal point well. The Zen practitioner utilizing the huatou method will experience “nagging undercurrents of doubt” (p. 15). That doubt, above all, is what drives this nonconceptual existential inquiry into original nature. “Who am I?” or “What is wu?” or simply “Who?” or simply “What?” clip clops and clip clops until, in time, it can gallop forward on the strength of the aching hunger to know.

I imagine you caught that last poetic phrase: “the aching hunger to know.” For truly–and the Three Greats in Chan makes this abundantly clear–the genuine mystic must have Great Doubt and Great Faith. The Cloud author gives, methinks, short shrift precisely to “the frame” (namely, his own version of Great Doubt) even as he urges one to keep “beating” on “the cloud of unknowing” with that humble yet persistent “stirring of love.”

Sri Ramana Maharshi often says, “Inquire into the Self or surrender completely to God.” While these two seminal, and basic, paths–to wit, that of jnana and that of bhakti–start off on different feet, they are braided together throughout in mysterious ways–sometimes Faith predominating while at other times Doubt does, yet in the end, as T. S. Eliot once wrote “is also my beginning,” they converge to a point at which they become, as in a sense they always were anyway, one and the same.

Purification, Humility, And Superabundant Love In The Cloud Of Unknowing

“The cloud of unknowing,” according to the author of this Christian mystical text, is that state ‘partway’ (we might say) between our highest nature and God in himself. Unknowing is relative to what it is that human beings claim to know by drawing on “the bodily sense” and on the intellect. To not know in a mystical sense is thus to enter to enter into a “cloud” where neither the bodily sense nor the intellect nor any other faculty for that matter can aid us.

Prerequisite: Purgation

Is there anything that one must do in order to prepare for embarking on this path? The Cloud author urges all would-be contemplatives to “cleanse their consciences of all the particular sinful deeds they have previously committed, according to the accepted requirements of Holy Church” (The Cloud of Unknowing and Other Works, ed. and trans. A.C. Spearing, p. 52).

This is sage counsel and for two reasons. Firstly, a number of mystical traditions impress upon the spiritual aspirant the preliminary need to lead a virtuous life. Not infrequently, certain virtues are enumerated and are to be cultivated. For ethical and for spiritual reasons, one needs to have the right constitution to engage in this existential inquiry into the nature of the ultimate.

Secondly, leading a virtuous and wholesome life makes possible an opening tot his inquiry in the first place. One can’t really begin in earnest (save, any good Christian would say, for the grace of God) if he is living quite sinfully. There will be an immense cloud of sin and ignorance–neither, to be sure, a “cloud of forgetting” nor a “cloud of unknowing.” Both of these will remain occluded from view, well beyond his grasp.

Purgation, “cleaning oneself up” and leading an orderly life, is therefore the chief prerequisite.

The Cloud of Forgetting

After and as one purifies one’s soul, one is able to begin placing in the “cloud of forgetting” all matters external to the inquiry into God in himself. Where Advaita Vedanta would speak of asat, or the unreal, and where Buddhists would recommend vigorously yet gently “letting go” of any transient phenomenon, The Cloud author speaks of a “cloud of forgetting.” The practice entails putting everything creaturely into this cloud.

We may call “forgetting” an act of vigorously putting aside everything else so that the sole objective–being one with the divine–can come so fully into the foreground that it cannot, henceforth, be lost sight of.

The cloud of forgetting, then, is in the service of the cloud of unknowing, and the cloud of unknowing is “a strong signal” to God that one is so filled with earnest, humble longing and stirring that one is completely open, ready, and fully surrendered to him.

Humility and Superabundant Love

What seems to me of central importance in The Cloud is the ontological dependence of the creature on the Creator. Humility, on The Cloud author’s view, is the natural virtue to embrace whenever one fully comes to grips with “humanity’s impurity, wretchedness and weakness” (p. 37). Original sin is the state of such weakness.

The recognition must go deep into the heart. “I am not enough. I am weak. I can’t do.” And this recognition is religious, not psychological. By this means am I humbly aware of all is wanting in me owing to my prideful stance of ontological independence.

Humility, stemming from the recognition of human weakness, is set over and against God’s “superabundant love” (p. 37), which the mystic must also appreciate. That love, says The Cloud author, is so great, so complete, so awesome that it cannot be fathomed by the human mind or heart.

Humility and superabundant love set out ‘the terms of separation’ and the longing for union. The only thing left to do is to surrender completely.