3 • What are Wit, Wisdom & Wiles?

What are Wit, Wisdom & Wiles?

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Ahoy friends. Welcome to the third episode of “Wyrd Work with Dr Fox”—the third of three “foundational episodes” I wanted to share before we wend deeper into the wilds.

Having explored “What is Wyrd Work?” and “What is a Liminal Agent?”, this episode now attempts to unpack the tagline of the podcast itself. That is, “a podcast ostensibly offering wit, wisdom and wiles for living and leading in this time betwixt worlds.” Sounds good, right? But what does it even mean?

Here’s the tl;dr:

— Wit for sensing —
— Wisdom for discernment —
— Wiles for enactment —

Each has its own shadow when cut loose from the other two—which is why I hold them as a “trialectic.” I like trialectics because they bring a fruitful generative dynamic distinct from a more conventional dialectical approach. (You can read more about this via Dave Snowden’s piece: Trialectics, or thinking in threes)

As ever, this episode wends. Together we amble through themes of “optionality collapse,” the Listening Society being cancelled (the Meaning Crisis, too), the trouble with hope, and the perennial question: what it is that is ours to do?

⟠ The transcript (lightly edited)

00:00 Huzzah, we are back

Huzzah and what-ho, we are back, friends. I’m Jason, and this is Wyrd Work with Dr Fox: a podcast ostensibly offering wit, wisdom and wiles for living and leading in this time betwixt worlds.

This is the third of three foundational episodes I’d been planning before I get all loose with it. In this episode we’re going to be exploring: what is wit, wisdom and wiles? What are wit, wisdom and wiles? Here I am, talking about wit, wisdom and wiles for living and leading in this time betwixt worlds, and it sounds good—but what is it? What is it, even? We shall unpack that a little today. It’s a favourite topic, and I intend to wend. Once again.

I have a copy of James Geary’s book Wit’s End in my hand—a phenomenal book—and I might quote from it a little today. I’ve also got Lewis Hyde’s Trickster Makes This World within reach; you know, the usual things. But anyway: I’m so glad you’re here. Thank you for listening.

05:47 Cheap intelligence, and optionality collapse

I was reading an article from Indy Johar: “Living in a Hyperinflationary Knowledge Economy.” Knowledge and analysis are spreading faster, making individual insights less valuable and increasing the risk of shared mistakes. This is part of what any of us complexity practitioners are feeling in the zeitgeist, in the noösphere. We have such ready access to cheap intelligence that we are drowning in cheap intelligence. Synthesis is probably going to be such an important trait amongst us all—but this requires the wit, wisdom and wiles I shall be talking about in this episode.

On the note of Indy Johar: I had the delight of working with a friend who is the CEO of a wonderful financial services firm, and together with the team we had a viewing of Indy Johar in conversation with Nate Hagens on The Great Simplification podcast—one of my top three favourite podcasts. This was a conversation about optionality collapse: the likelihood of the myriad existential risks happening in finance, and the spill-on second- and third-order effects of anything, really—from El Niño affecting food, through to the social contagion that can happen when people experience what they code as a “nutrition risk event,” which is code for famine. It’s pretty grim and heavy. Except—I mean, these are the waters I’ve been swimming in for some time.

And it was this weird experience of realising: hmm. I feel so alien. I feel so alien, sometimes. When I’m hanging out with folks outside of my liminal agent network, I need to get better at relating to the everyday chit-chat that happens. It’s not a case of dumbing things down, but—even thinking back on the last couple of podcast episodes—there was some cerebral heft required. Perhaps this was the blessing of being a little run down of late: you really do need to slow down. One of the shadow sides of wit is that it does lead to a kind of alacrity—a quick-wittedness, which is generally how wit is considered. And I want to expand that, so that wit is not merely a function of the speed of insight. But before we get to that, one other reckoning.

08:43 The Listening Society is cancelled

One other reckoning that has come to me recently is from Emil Ejner Friis—I don’t know if I’ve ever said his full name—one of the two writers behind Hanzi Freinacht, author of The Listening Society, a phenomenal book I was enamoured with ten years ago. He has written a piece that effectively says: the Listening Society is cancelled. The pathway we are on is towards what he articulates as a postmodern dark age, not a metamodern “regenaissance.”

There’s a particular line in there about how we were closer to a listening society ten years ago than we are now. A listening society being a deeper kind of welfare—one concerned with the co-development of all of us; creating the conditions for mutual flourishing, for psychological and depth development. We were closer to that ten years ago. Let me quote from a little comment he wrote on Substack:

A listening society, which in the book by the same title has been defined as a deeper form of welfare system that addresses the psycho-social and higher emotional needs of every citizen from cradle to grave, can only emerge in a stable country with high-functioning institutions. The listening society builds on top of the existing welfare system, and it requires a good economy, geo-political stability, and a lot of people who have downloaded the metamodern code, and an even greater number of young working people to build the thing. Over decades. Those prerequisites are going away. Fast.

10:52 A world more curious and kind

So there was this kind of reckoning. As I think back to this, I was so enamoured by this potential. In parallel to this, probably around the same time, the attractor beacon—the pithy purpose statement I’d been using—emerged. This was back when “purpose-driven business” was quite the thing, along with the greenwashing and purpose-washing and why-washing. Simon Sinek’s Start With Why was popular back then, and so there was all this talk of purpose, and I felt that I needed a purpose statement. And so, to quest to co-create a world more curious and kind, and a future less grim probably emerged around there. It still lights me up. This is my orientating beacon: a world more curious and kind, and a future less grim. It seems particularly apt as the contrast increases—as we seem to be heading towards a world more certain and cruel, and a future more grim.

So it all remains there. But even as Emil acknowledges that the Listening Society is cancelled—and I remember chatting with him in the early days after Russia invaded Ukraine, and his commenting that most of the orientation of European governments was on a war footing, so the conversations were about how many submarines or tanks to buy, not how to invest in a welfare society—I feel that with the material shortages, and particularly the energy bottlenecks that are happening (with this voracious demand for the high-dimensional manifold space potentially offered by artificial intelligence), well: as is often the case in the fourth turning, societies will be orientating towards conflict. Towards war. This is not great. This is not what I want for the world.

And there is a chance that we can squint, and if we squint hard enough, we might find the eye of the needle that we may thread. I feel that it’s still useful to hold on to some sort of proxy of hope as an attractor beacon amidst this. Not that we need hope. There’s an acceptance of things as they are, and a curiosity for what may be, and a resoluteness to live in right relationship with others and in congruence with your own values. All of that holds true.

But the shifting in the signs is probably correlated with my own descent into the dark forest. As part of the deep lore I’ve alluded to, there was this kind of ego death that I experienced, as Dr Jason Fox went into the dark. I feel like it was a seven-year journey—I’m at risk of fetishising my own story here, but: two years of descent, three years in the dark, two years to climb out. And it was kind of triggered by the same realisation: that this orientating beacon has largely become too late, as with much of the climate stuff. And so our stance needs to adapt. The world we’re facing into has a lot of new challenges in this metacrisis we share, which is why the times call for wit, wisdom and wiles.

14:10 Hope is a queer trickster

Having said that—if you’re listening to this, well, I feel like I need to throw in some sort of token hope statement. I love Báyò Akómoláfé’s reference to hope being a queer trickster: the way hope plays with us, dashes our spirits and then renews them, and so forth. It is a funny thing to relate to hope.

Actually—I’ll tell you what, whilst we’re on it; this is not part of the plan—I recently reacquainted myself with David Chapman’s articulation of hope on his wonderful Meaningness site. He says:

Hope shifts imagined meaning to the future, when the present is obviously meaningless. Hope is harmful in devaluing the present and shifting attention to imaginary futures that may never exist. Hope causes emotional stunting and childishness. It is inimical to emotional growth.

So I’ve always had this funny relationship with hope. I’m okay with the disposition towards possibility and curiosity; an orientation towards the emergent, and towards right relationality with life. But I’ve found real solace in David Chapman articulating why hope can be harmful. I know Rebecca Solnit has written her books about hope, and even recently she was playing with the term resolute as distinct from hope—an acknowledgement that a lot of people, myself included, have some sort of allergy to hope.

16:20 The first hope, and the hope beyond hope

It seems like it’s necessary for us to have some sort of hope, and I feel like I do. It’s just that I’m so wary of the first hope. I’m talking about the hope beyond hope here. The first hope is where hope lies within the existing paradigm that gives rise to the conditions we’re experiencing.

I did an event for a group of education leaders a month or two ago. Part of my role here, I believe, is to have folks awaken to the moment we’re in—because there can be a lot of attachment to nostalgia, to how things were. I understand, psychologically, why that attachment is needed. But sometimes it can blind us to what needs to be done. There’s this tendency to hold out and hope that things will simply return to how they were before. But because of myriad factors happening in the world—peak oil, the energy demands of society, the cascading implications of extreme wealth inequality, the power laws that cement certain influences within the wider system we share—to locate hope within the existing paradigm is to simply perpetuate the conditions that give rise to the need for hope.

So I was chatting with this education leader, and there was an awareness of some of the ecological catastrophes of our times. But then there was the classic: “But there’s still hope, though. There’s EVs. EVs are getting cheaper.” And in that kind of stance—I mean, I can understand why people are grasping for it. But it’s not quite it.

At the same time: what are we to do? It’s so enormous, right? So we look sideways. We tend to what is ours to do.

18:05 What is it that is ours to do?

There’s a question from Gordon White, the magician who recently passed away, and I love this line from him: What is it that is ours to do? What is it that is yours to do?

If we think about this moment that we share—this fact that we are alive, experiencing life beyond the void we otherwise reside within (eternally, perhaps)—we have this precious moment, this precious extended moment of a lifetime, in which the question what is it that is ours to do? is really quite poignant. It gestures to the distinction between vocation and ambition; to the vocational calling. It gestures to meaningful progress as distinct from the delusion of progress. It gestures towards mythopoetic development: a kind of quickening, and a realisation of what it is that you are here to do.

Wonderful sages like Gurdjieff, who pioneered the Fourth Way, would probably delight in the conditions we have right now—because never has there been a better opportunity to practise intentional suffering and go against the pull of the machine; against the automaticity and the various entrainments that lure and hold our attention in places where it ought not be.

And so, again: there is still hope, but it’s beyond the conventional hope. Let me read a couple more things from David Chapman on the topic of hope. These are choice quotes, by the way.

Even in crises, hope can be harmful. Since eternalism consists of blindness to nebulosity, it is destabilized by anything that brings nebulosity to our attention. Fortunately, nebulosity is indirectly visible in everyday life, as uncertainty, surprise, endings, confusions, breakdowns, and disagreement.

[…]

Crisis, by destabilizing eternalism, can be an opening into either nihilism or the complete stance. We should prepare for this. In a crisis, we generally get caught up in strategic suffering—that is, frantically trying to get the world to go back to behaving the way we think it ought to. It is difficult then to think about what may seem like abstract philosophical concerns. Knowing that unwanted events are likely to tip us into nihilism, knowing how to recognize nihilism as we shift into it, and knowing the antidote to nihilism is the first step.

And then, finally:

The antidote to hope is active acceptance of the present as it is, and a prospective acceptance of the future, however it will be.

20:53 For every it was, I willed it thus

To kind of synthesise this: I was listening to Layman Pascal talk about Nietzsche in his conversation with my friend Tim Adalin. Nietzsche was one of the proponents of amor fati—love of thy fate. And for me, and for the notion of wyrd work—which is effectively working with and within the tapestry of fate; not in a predeterministic way, but working with what is, and what may yet become—I really like this line. In Layman’s terms, Nietzsche’s stance is: for every it was, I willed it thus.

For every it was, I willed it thus. One must engage in life as though every outcome is something you have willed for yourself. This is part of what it means to have agency: the perspective you bring. The situation you are in right now, as you listen to this, is exactly what you have willed for yourself. And sometimes the negative or challenging or trying circumstances we find ourselves in are the very circumstances that lead to depth and growth and wisdom. Whilst in the moment it might not feel great—like if you’re on a long hike, and it’s day four, and you’re going uphill, and you’re tired and sore and the end doesn’t seem in sight, and you’re thinking, why am I doing this?—later, you’ll be at a vantage point that would not have been possible otherwise. And it will all make sense. So: for every it was—you willed it thus. And here we are.

22:36 The meaning crisis is cancelled, too

Just to loop back to Emil’s recent piece on the Listening Society being cancelled. Sad as that may be, the silver lining, as he points out, is that the meaning crisis has been cancelled, too. About ten years ago—maybe eight, I can’t remember—John Vervaeke’s Awakening from the Meaning Crisis, an exquisite lecture series of fifty-plus lectures on the predicament of meaning, really resonated at the time. But now there are so many abundant opportunities to find meaning, you don’t even have to try. Here, let me read the concluding piece from Emil:

Hence, at the end of the day there’s a glistering silver lining to the whole ordeal: If everything is fucked, and untold horrors are to descend upon humanity in the coming decades—that also means that the meaning crisis has been cancelled as well. Never has there been so many venues of heroism available to the common person with the uncommon cunning and determination—so many lives to save, so many local catastrophes and tragedies to avert, and so much fucking meaning to squeeze out of the sad, sad state of contemporary samsara.

So there’s a silver lining. The meaning crisis is cancelled. It’s great. And I agree: it has never been easier to find meaning. If you live in America, you may have ICE patrolling the streets—look after your neighbours, look after your community. In many places there may be food shortages—learn how to grow, learn how to share. We are in a situation of increasing state surveillance—learn how to look after each other. This orientation towards a world more curious and kind and a future less grim starts with—well, I’m not sure if it starts with, but a large feature of it is this relationality. This disposition.

24:31 Subversive leadership

This is why, as organisations hollow themselves out under the logic of the machine—where people are literally burning themselves out right now, sacrificing everything they love to get what they think they want (a classic Molochian bargain)—the only way to avert the impending hollowing is via subversive leadership. And this requires wit, wisdom and wiles. If you are too overt about this, you will reveal yourself to be out of alignment with what the system wants, and you will find yourself out of employment. In this multipolar trap, with its rivalrous dynamics, work itself has become “scarce” (in inverted commas) because of the demented era we share. So overtness is not necessarily a good strategy.

The reality is that we are living amidst this metacrisis we share, which gives rise to the polycrisis, which gives rise to the myriad finite games—which are themselves fine and natural; we step into and out of these as infinite players. But it does require us to be a little more subversive. And by subversive leadership, I mean changing the underlying conditions that give rise to the kinds of behaviours we see.

By underlying conditions, I mean—let’s hat-tip back to the definition for wyrd work. Wyrd work means attuning to, tending to, and sometimes deftly perturbing the underlying conditions of an entangled system, so as to quicken and catalyse development, emergence and change. Part of the work of subversive leadership is in being attuned: having the wit, wisdom and wiles to know when to deploy humour; when to tweak things; when to subvert things.

Having said that—all right, let’s get into it, because I’ve alluded enough. Thanks for staying with me.

26:55 Keep your wits about you

So I’ve got this book in my hand. Let’s look at wit. Wit, wisdom and wiles—you’ll hear me talk about wit quite a bit. It’s a funny thing to talk about.

The word wit comes from Old English. It originally meant “mind” or “understanding,” and there is the verb witan, “to know.” The sense of quick verbal cleverness only became dominant around the sixteenth and seventeenth centuries. Before that, your wits were your faculties of perception. Which is why, when I say keep your wits about you, I’m talking about noticing what you notice. Having the perspectival acuity to recognise what is going on—not just from your own perspective, but from other perspectives, too.

Perspectival acuity, as I recently wrote in my newsletter, means recognising that you have a perspective; understanding what that perspective is—its affordances and limitations, what is granted by it and what is hidden—and then knowing that the same situation can look different from others’ perspectives. If you can step into others’ perspectives and, through that, arrive at a kind of mercurial synthesis of it all—which allows you to shapeshift situationally, as befits the context as it emerges and unfurls—then you have your wits about you.

And so I really want to de-emphasise this quick-wittedness. I’m a twelfth-house Mercury combust, and so I’m fused with Hermes, and I tend to get a little carried away in the hermeneutics and the cerebral flair. Much to my—well, I often regret it. The common thing for me is that I could slow down. And sometimes it feels like I’m going slow—patronisingly slow, even—and I don’t like that. I like relating to you as a peer. But still, it’s a courtesy. This is part of the curse of knowledge I spoke of in the last episode of season one. One becomes so familiar with the terrain that they forget what it’s like to be new to the material. Someone with the curse of knowledge tends to gloss over some pretty important stuff, because they’re keen to get to the bit that excites them, when there are foundational materials at play. Hence why I’ve been trying to do these three foundational episodes—so that at least when I’m talking about wyrd work, or what a liminal agent is, or wit, wisdom and wiles, I have some sort of reference point. We’ve got the ground covered.

So: I have this book, Wit’s End by James Geary. I think this came out in—let’s see—2019. Yes, 2019. Let me share some quotes with you.

29:55 Mētis (wit + wisdom + wiles)

You’ll sometimes hear me talk about mētis. Mētis was Zeus’s first wife, the goddess of wisdom and cunning. Her name gradually came to be used to describe anyone who deploys ingenuity, resilience and deceit to overcome adversity. All of this is very fox-like; it’s very fox-coded. I can’t help it. The fox is a liminal creature betwixt field and forest; a boundary crosser; a messenger between worlds. So mētis and fox—this is practical cunning; a pragmatic wisdom and cleverness. I really like it.

I’m now quoting from Marcel Detienne and Jean-Pierre Vernant’s Cunning Intelligence in Greek Culture and Society, via Geary:

Mētis is a way of thinking and doing exercised in situations of emergency or crisis in which solutions are neither logical nor obvious. Persons of mētis show their mettle through a complex but very coherent body of mental attitudes and intellectual behaviors which combine flair, wisdom, forethought, subtlety of mind, deception, resourcefulness, vigilance, and opportunism.

So you can see, given the situation as I’m articulating it—a potential descent into authoritarian dystopia; corporate fascism; a surveillance state in which life-sustaining ecologies are increasingly destroyed to fuel an economy blind to the harms it causes—you can see why some mētis could be handy for us in amongst all of this.

32:25 Stance, not mindset

Let’s see. There’s a great quote here from the book. I’ve dog-eared a few pages, so it’s surprising me as I come across it. Here’s another one:

We have an innate ability to hold in our minds multiple meanings about the same thing at the same time. Which meaning ultimately emerges as primary depends on the experimental conditions and, crucially, on the disposition of the observer.

So—I’m not a fan of mindset as a word. I understand why people want it, because people have a very low tolerance for ambiguity, complexity, volatility, paradox, doubt, nonlinearity and change. So people want it to be set; to be fixed, like concrete. “You just need a growth mindset.” Actually, growth mindset is pretty cool. I like that one. But I tend to use words like stance more than mindset.

If you think about martial arts, you can have different stances. You can crouch low, one hand in front of you. You can be in Brazilian jiu-jitsu and be on the ground. You can be nimble and sprightly upon your feet. Each stance brings about a different disposition. With your disposition, you have an orientation towards a certain style of engagement. And this disposition, this orientation, this stance—it effectively brings up different affordances.

And so the mercurial, fluid mode tends to be a way of holding optionality, and not prematurely collapsing the optionality space into a fixed outcome. This stance—this fluid, mercurial, both/and, transperspectival, multitude-containing orientation—is useful when we are in this time betwixt worlds, where we don’t have the stability we could rely on from previous experience, but at the same time we’re not certain what will befall us.

34:14 Negative capability and meta-rationality

This is the same thing the poet John Keats would describe as negative capability: the ability to persist amidst paradox and ambiguity without irritably grasping for certainty, for closure, for something to hold on to. This is part of meaningness—the ability to dance amidst nebulosity and pattern. This is part of the quality of meta-rationality: the ability to discern between rational systems without being limited by any single one of them. And this is part of what I talk about with more-than-rational sensibilities.

35:07 Bricolage and the acuity for anomaly

I’ll probably just do one more quote from this book. I’m not sure what the experience is like as a listener, hearing someone read quotes from a book you don’t even know about. But anyway. I just want to say one more thing that is a quality of wit, and that is bricolage. This is also a quality of the trickster. You heard me quote Lewis Hyde, from Trickster Makes This World, in the last episode:

Better to operate with detachment, then; better to have a way but infuse it with a little humor; best, to have no way at all but to have instead the wit constantly to make one’s way anew from the materials at hand.

This is the bricoleur. And here’s the quote—where is this quote from? Okay, I think this is actually from James Geary:

Serendipitous wits are first-class noticers who pay keen attention to their environment, make strategic observations about anomalous or unusual aspects of the objects and people around them, and translate those observations into actionable insights or useful interventions.

This is why part of wyrd work is the acuity for anomaly. Once you are attuned within a system, you then have a subtler, more refined acuity for—and attunement to—any anomaly. This is why it’s ridiculous when external consultants come in with the answer before having spent time attuned within the system itself. How could they possibly know what the system wants? This is also why, in complex domains, expertise is de-privileged. The folks working directly with customers or clients, or working in the field, are usually best situated to notice these anomalies. But the incentive landscape—the energy gradients—usually precludes them from doing so, because there’s so much work to get done. In many cases people are disincentivised from raising observations about stuff that’s odd. And many organisations are so siloed anyway that there’s no capacity to compare notes.

In an ideal sense, we would have ways to cohere across silos. I’m not anti-silo. Silos are great for actually getting work done. It’s good to have coded language internally, and a shared expertise, so as to do technical things swiftly, with expedience and depth. But it needs to be coupled with some sort of knowledge sharing. These things resist formalisation as interventions—but we can create informal pockets in which the conditions are conducive to folks relating, and sharing what has been noticed. Patterns can emerge there. And that is great insight and intel for what could be the early weak signals that an opportunity or threat is emergent, and that things need to change.

Back to the quote:

These kinds of do-it-yourself wits are what the French anthropologist Claude Lévi-Strauss called bricoleurs, individuals skilled in making things from odds and ends, scraps and rejects, and whatever else they happen to find at hand. Lévi-Strauss used bricoleur to describe how cultures assemble myths from bits and pieces of ancient stories, but the term applies equally well to people who use wits quickened into serendipity to build something beneficial from bric-a-brac.

38:31 Wit for sensing, wisdom for discernment, wiles for enactment

So: wits. Hopefully I’ve done a bit of a service to what I mean when I say wit. Wit is largely for sensing. And for wit, wisdom and wiles, I’ll give you the tl;dr at this point in time: wit for sensing, wisdom for discernment, and wiles for enactment.

Wit. This is where I would love to be more in conversation with folks. I do have this tendency, when I host folks on this podcast, to be far too gracious as a host. Sometimes I really want to challenge, or poke and prod and perturb folks—but then I think, I’m too polite, and I just don’t know if they’d be able to handle it. It’s an odd thing to record your voice on a podcast, because in this hostile attention economy people can use your words against you, take them out of context and so forth. But fuck it, I say.

39:41 Sophia? I barely know her

All right, let’s look at wisdom. I shan’t go into as much depth on wisdom and wiles as I have on wit.

Wisdom comes from Old English: wīs, meaning wise, plus -dōm, meaning judgement, decree or condition—as in doom. You might also notice wīs in the word wizard, which is from Middle English and means “wise one.” I’m a big fan of wizardry. And wisdom itself—you may have heard me say this before; I really like this definition, though it’s only partial—is to discern the path of least unnecessary suffering.

40:41 A trialectic, and its failure modes

The failure mode of wisdom is a passive equanimity that never acts. Which is why I’m placing wit, wisdom and wiles in a kind of trialectic. You don’t want to have just one and not the others.

Too much cleverness with the wit—it’s great, but it never becomes judgement. You’re too slippery. You’re not actually committing to anything. You have no skin in the game. You’re very fancy and clever with all your fancy words—but what are you standing for? Wisdom, on the other hand, has the failure mode of being so at one with it all that it never acts. And then wiles, when we get to that, has the failure mode of efficacy cut loose from purpose. Just because you can doesn’t mean you should. There are a lot of wily business folk out there who are not necessarily intellectually honest.

I really like wit, wisdom and wiles in the sense that you’ve almost got head, heart and hands—or things like that. The trialectic works, and it holds across these things.

42:00 Smuggling wisdom

We’re in an era right now where intelligence vastly outpaces wisdom. A lot of the initiation and cultural practices that have served humans pretty much since humans have been humans have rapidly eroded away. Now, who knows? Who knows what might emerge: this kind of scrambling, this syncretism cultivated across so many displaced cultures; this adaptability, this bricolage; this smuggling of wisdom. I often say that I have to smuggle wisdom into organisations with the work that I do. Folks are enamoured by the intelligence, the rationality, the objectives, and so forth. But wisdom is warm and dissolving. It’s humbling, in many senses.

If I were to talk about some of the tenets of the school of fox wizardry that is coming—wit, wisdom and wiles—we’d be talking about wisdom as intellectual honesty, wit as memetic fitness, and wiles as commercial savvy: the components of being an effective liminal agent and independent consultant in this time betwixt worlds. But wisdom is not attractive. People will nod—“mm, yeah, yeah, wisdom, of course”—but still be enamoured by the shiny, bright, salient intelligence. And this is interesting in a world of rampant artificial intelligence: the allure of cheap intelligence, easy answers, quick fixes and such. Nothing new here, necessarily; just the same patterns amplified like never before.

43:55 Discernment and meta-rationality

Discernment is the word I think of when it comes to wisdom. And this is why wisdom has such an important role amidst this explosion of artificial intelligence. Wisdom works alongside meta-rationality, and meta-rationality is exactly what’s needed to be able to discern the outputs of the artificial intelligence that’s being used. This is a function, in some senses, of the way meta-rationality takes into consideration aesthetics and taste, purposes and contexts. (Big appreciation to David Chapman’s elucidations on this). It considers things from different perspectives and timescales, and all of that becomes synthesised quite rapidly—with mētis, I guess, as I was talking about. So there is a bit of an overlap between wit and wisdom, with mētis bridging the two.

44:52 The peril of wisdom

There’s a slight peril with this wisdom stuff, too. If wisdom itself is emphasised too much, it becomes a little bit bovine, in some senses. There’s an acceptance of things as they are. And that’s frustrating for me—because whilst it may be useful and true, and as I quoted from David Chapman about the antidote to hope being an acceptance of things as they are, I do think there is something to be said about enacting thy will. If you have a vocational calling; if you have whim; if you have something that calls to you—that exists from a place other than wisdom. Like mystery, and so forth.

Wisdom is good. I want wisdom. I would love for us to co-create a world more curious and kind, and a future less grim. I would love to see us all cultivate greater wisdom as a society, together—if we could mitigate and minimise the unnecessary harm enacted upon so many animals, so many societies, so many countries. That would be the path to go down.

46:12 The Cleverness, a precursor to wisdom

I remember when I had the business name The Cleverness. The Cleverness was the name of my skyship, sailing through the skies of the noösphere—very Zephyrus. But it was also going to be the name of the publishing company I had back when Kim and I launched The Cleverness Biannual: Thoughtful Provocations for the Quietly Dissatisfied. A magazine of philosophy, business and artistry which, in the making of it, had us realise just how unprofitable it is to make a magazine—unless you’re getting sponsorship and ads, scaling up the business, and willing to pulp heaps of copies if they don’t sell. It was a beautiful, beautiful art piece. But we also burnt out in the process of making it.

One of the taglines I had at the time—and it’s still there on the old cleverness.com website, which I’ll soon be closing as everything folds into The Skulk—was: The Cleverness, a precursor to wisdom. And I do feel that wit is a precursor to wisdom. The cleverness brought about by wit is the perception of possible ways of enacting things.

47:22 Wiles: enactment and weak probes

Which brings me to wiles. Because wiles is the enactment, and it is the weak probes. The weak probes you make by enacting the cleverness and the wit you have—these give you insight. That’s how you make mistakes. Or you have successes that lead to insight. Either way, you get experience from this. The experience is integrated into your character, and it cultivates wisdom.

47:51 Levelling up as characters

Although—actually, one lens we could take is that society nowadays has become so averse to challenge, to perspectival acuity, and to anything difficult or involving friction, that we’re not actually levelling up as characters. We’re not getting the experience points. We’re not integrating life’s experiences. And as a result, we’re all very low-level characters who have displaced experience with collecting material goods, or collecting status on social media, or trying to add extra digits to the bank account. These are substitutes for the poetic disposition to life, in which we live the poem we were born to be. In which we stumble; we make mistakes; we lose ourselves; we find ourselves; we have our hearts broken—and so we have the deepening of empathy, and all of the things that make for a character that has some depth to it. We don’t really have as much of that.

49:00 Wiles, wiliness and the fox

So wit, wisdom and wiles is a trialectic. Wiles itself comes from Old English wīl, a trick or stratagem. Its origins are disputed; it could possibly come from Old Norse vél, which refers to artifice or craft. And guile is very likely its doublet.

Yes: wiles. I like wiles. I like wiliness. Wiliness is a characteristic of the fox. It’s the ability to enact things that may not yet be wise—but we will know whether they were wise or not on the other side of it.

And so again: wit, wisdom and wiles. Wit for sensing, wisdom for discernment, wiles for enactment. This trialectic is necessary for liminal agents to be effective in this time betwixt worlds. I’m not going to say that with the three of them in cohort you’ll always be successful. But it’s the dynamics of the engagement in this time betwixt worlds. If you over-index in any one without the others—if you’re really wily, great, you can trick folks, wonderful; but what of your heart? What of your soul? Likewise, if you’re really witty, really clever—great, but what are you standing for? Or you’re really wise—wonderful, you’re at one with it all; you have transcended the petty aspirations of common folk who look upon you as so wise, so wise. But what are you actually doing, though? Are you paying attention to what’s happening in the world? Where are you enacting things?

51:02 Living and leading

So: wit, wisdom and wiles. And as I say in this podcast—Wyrd Work with Dr Fox, a podcast ostensibly offering wit, wisdom and wiles for living and leading in this time betwixt worlds. Living and leading. Leading is a funny one. I’m still not a fan of the words leadership and lead, but for want of a better word, it still gestures towards this notion of enactment. Not merely living—although living is a beautifully potent word—but leading. You’re actually leading, at the very least, yourself. You’re enacting things. Wit, wisdom and wiles for living and leading in this time betwixt worlds. There you go.

Hopefully it makes sense. Who knows? Who knows who listens to all of these in depth? But it’s good for me to articulate what I mean when I say these things. As a wizard, words are incredibly important. They shape meaning; they shape the reality we share. There’s a lot of thoughtfulness that goes into the discernment of—well, sometimes I come by whim. But there’s an aptness to it. An aptness; a fittedness that serves well, in a generative way, for the context we’re in.

52:35 Finding the others

I dare say that us liminal agents—we are few. We are not many. There aren’t many who have whatever it is that goes into shaping us; who have the wit, wisdom and wiles to recognise that we are in a time betwixt worlds, and that we have the ability to play a part in shaping that which is to become. It’s nice to find the others.

53:49 Lighting the beacon

Plenty more from me in the days to come. I might loosen up the format of this podcast. I like flying below the radar with this, but there is part of me that feels like I need to get better at showing up on the open web, and lighting the beacon for others to find us. So let’s see what happens there.

As ever, thank you so much for listening. Whatever comes next, I’ll leave it open to whim. Let’s see what emerges. Together, we quest for a world more curious and kind, and a future less grim. See you soon.

Works cited

Here are some links to things mentioned in this episode, roughly in order of appearance.

• What is Wyrd Work? and What is a Liminal Agent?, episodes 1 and 2 of this podcast (2026)
• James Geary’s book Wit’s End: What Wit Is, How It Works, and Why We Need It (2019)
• Lewis Hyde’s book Trickster Makes This World (1998)
• Indy Johar’s essay “Living in a Hyperinflationary Knowledge Economy” (2026)
• “Optionality Collapse: We’re Investing in a Future That Won’t Exist”, Indy Johar in conversation with Nate Hagens on The Great Simplification, episode 238 (2026)
• Emil Ejner Friis’s essay “Next Stop—Postmodern Dark Age, Not a Metamodern ‘Regenaissance’” (2026), and his follow-up note on the prerequisites of a listening society
• Hanzi Freinacht’s book The Listening Society (2017)
• Simon Sinek’s book Start With Why (2009)
• William Strauss and Neil Howe’s book The Fourth Turning (1997)
• My own “Out of the dark forest” (2024), for the deep lore
• Báyò Akómoláfé on hope as trickster, via my museletter “Do you even leap?”
• David Chapman’s page on hope, from his hypertext book Meaningness; see also his site on meta-rationality
• Rebecca Solnit’s essay “This is really hard, but we are not quitting: reflections on kindness and resoluteness” (2026)
• My museletter “Are we beyond hope?” (2023)
• Gordon White’s Rune Soup, where the question “what is it that is ours to do?” is a refrain
• My museletter “Firesides, ambition & vocation”, and “the delusion of progress”
• G. I. Gurdjieff and the Fourth Way; see also Layman Pascal’s book Gurdjieff for a Time Between Worlds (2024)
• “What is Power, Really?”, Layman Pascal in conversation with Tim Adalin, Altered States of Conversation (formerly Voicecraft), episode 151 (2026). The “I willed it thus” line is Nietzsche, from Thus Spoke Zarathustra
• John Vervaeke’s lecture series Awakening from the Meaning Crisis (2019)
• Scott Alexander’s essay “Meditations on Moloch” (2014)
• My museletter “Subversive leadership”
• My museletter “Perspectival acuity” (2026)
• “Knowledge of Curses”, the final episode of season one of this podcast (2025), on the curse of knowledge
• Marcel Detienne and Jean-Pierre Vernant’s book Cunning Intelligence in Greek Culture and Society (1974; English translation 1978)
• My museletter “A Stance on ‘Mindset’” (2023)
• John Keats on negative capability; see my “Negative Capability—the antidote to change fatigue”
• Claude Lévi-Strauss’s book The Savage Mind (1962), where he introduces the bricoleur
• My post “Conditions, not solutions” (2025)
• My museletter “Intellectually Honest (like a fox)” (2023)
• My museletters “hollow fluency” (2026) and “Wisen up about AI—12 recommendations”
• The Cleverness Biannual, and the old cleverness.com website
• The School of Fox Wizardry