Firesides, ambition & vocation

In my episode on How to Host a Strategy Offsite from a few months ago, I made reference to ‘sleeper agents’. These are fellow infinite players who move quietly and plant things, deftly working their way into positions of influence and authority within larger organisations/egregores, biding their time for that kairos moment in which significant change can be brought about.[^ Kairos is one of two words that the ancient Greeks had for ‘time’; the other being chronos. Whereas the latter refers to chronological or sequential time, kairos signifies ‘a good or proper time for action’. Where chronos is quantitative, kairos has a qualitative, permanent nature.]

I romanticise this role, of course. The reality of it would involve much that is tedious and trying. But still—it’s a role some of us are called to play.

On firesides

Last week I met a few sleeper agents at an event that a Singapore-based multinational was hosting for their executive clients.[^ I could tell because they were executives already subscribed to the museletter.] It was a lavish affair, held at a mansion replete with many candles, a violinist, and a sumptuous dinner (followed by smores and music under the stars and by the fire).

Ostensibly, I played the role of Dr. Fox—“wizard-philosopher and futurist”. In this guise I thus wove some foxmagic in service to the event. The briefing was not so much about providing content so much as it was about catalysing a warmening and deepening into context. In other words: my ideal briefing.

Dr. Fox is a mostly consummate professional; a gentleman-rogue, amongst other things. But we are both blursed with intellectual honesty; a career-limiting affliction in this attention economy.[^ Much like the curse of knowledge (which we both also share). The perils of wizardry, I tell you! Oh, and blursed is a portmanteau, of course. But you knew that!]

Thankfully, the client didn’t want a futurist to simply sell a glossy vision of the future, drunk on techno-optimism and AI-hype. Nor did they want some libidinally-sapping doomster come to warn us of the grim times ahead.[^ Which is possibly what I would have brought if I had been hired during the spell in which I was in a particularly dark chapter of life, soon after my metacrisis insight-cascade.] Instead, they wanted someone of a post-tragic disposition who could help the assembled folks to each look unto the future with eyes wide open—so that they might better find and feed the leaks.

When I speak these days I mostly channel.
(/¯◡ ‿ ◡)/¯ ~

There’s nothing scripted; it’s all enacted via enlivened attunement to the emergent context.[^ Of course: informed and influenced by the immersive briefing calls I do with my clients. And yes, this is more the style of a sorcerer than a wizard, I know.] This takes awareness, acuity, alignment, and attunement—not to mention wit, wisdom & wiles. Suffice to say: the event went incredibly well.[^ As they almost-always do.] And this is mostly because we—the event organising team and I—attended to the conditions that allow for emergence.[^ Epiphany cannot be forced; it must be evoked.]

My message was and continues to be:

Keep your wits about you.

But this particular audience[^ Senior executives from a range of large organisations, appropriately jaded and fatigued by standard speakers and events.] genuinely appreciated the opportunity to have an honest conversation about what’s happening, and what might yet emerge. Particularly given that we are in ‘The Fourth Turning’.[^ More deeply, we might hear this expressed as the metacrisis (which hosts the polycrisis), The Great Unravelling, The Great Simplification, The Long Dark, and so on.] In this current chapter, we cannot rely on our own past experience as much as we might like. Nor can we trust in enduring coherence. We’re right in the midst of a civilisational phase-shift into an unknown attractor-basin. This could be glorious. This could also be a slide into authoritarian and (further) ecological dystopia—a cyberpunk future of extreme wealth inequality, ubiquitous corporate surveillance, environmental degradation, mass extinction—and more![^ Likely “without even the virtue of cool aesthetics”—a line I got from Nikhil Suresh’s essay on a related matter. Also, astute readers will know that this is with my friend Simon Waller—The Future of Continuity (of the machine).]

We have to keep our wits about us.

The way through all of this remains non-obvious. Those who cling to any conviction about the future—any neat ‘solutions’—will likely be wrong. And those who ‘wait for clarity’ will likely miss their kairos moment.

It’s messy, complex, dynamic, emergent—and it embeckons our humbling and enlivening participation.

One of my favourite quotes—something that has inspired the fireside provocations I conjure—comes from a ‘half dandified trickster and half minimalist seer’ mystic known as James Lee Byars:

To arrive at the edge of the world’s knowledge, seek out the most complex and sophisticated minds, put them in a room together, and have them ask each other the questions they are asking themselves.

We need contexts within which we can cohere and make sense of things, together. To imbibe and enrich our proto-synthesis with new perspectives, so that we can see the world and our adjacent possible in greater resolution.

We also need contexts within which it is safe to talk—candidly and in good faith—about what’s happening in our world. Nay, not even just safe, but rather—enlivening and generative.

I experienced this the week prior, where I once again served as wizard philosopher-provocateur for a fireside gathering—this time with a room of very successful founders and entrepreneurs.

On ambition

These are folk with high agency+autonomy. Many struck me as ‘construct-aware’.[^ This means: being aware of constructs. ( ¬ᴗ¬) Haha, I jest. Here’s a paper on The Construct-Aware Stage of Ego Development and its Relationship to the Fool Archetype.] I also sensed that quite a few are in a chapter of life that we might call ‘post-achievement’. Here, the accumulation of yet more monetary wealth isn’t the primary driver—something more meaningful and profound beckons.

The thing that ‘high agency+autonomy’ folks have in common with sleeper agents is that there is a yearning to manifest an affect[^ Yes, affect.] that is greater than themselves. (Actually, it is true of all of us—regardless of the domain in which we work.)

This isn’t merely an act of ambition. ‘Ambition’ doesn’t quite cut it—as it’s a word in service to the small self. Or, as David Whyte writes in Consolations: the solace, nourishment and underlying meaning of every day words—

“[Ambition] is a word that lacks any real ambition, ambition is frozen desire, the current of a vocational life immobilized and over-concretized to set, unforgiving goals. Ambition abstracts us from the underlying elemental nature of the creative conversation while providing us the cover of a target that has become false through over-description, overfamiliarity or too much understanding.

The ease of having an ambition is that it can be explained to others; the very disease of ambition is that it can be so easily explained to others. What is worthy of a life’s dedication does not want to be known by us in ways that diminish its actual sense of presence. Everything true to itself has its own secret language and an internal intentionality with a secret surprising flow, even to the person who supposedly puts it all in motion. Ambition ultimately withers all secrets in its glare before those secrets have had time to come to life from within and then thwarts the generosity and maturity that ripens the discourse of a lifetime’s dedication to a work.

We may direct the beam of ambition to illuminate a certain corner of the future world but ultimately it can reveal to us only those dreams with which we have already become familiar. Ambition left to itself, like a Rupert Murdoch, always becomes tedious, its only object the creation of larger and larger empires of control; but a true vocation calls us out beyond ourselves; breaks our heart in the process and then humbles, simplifies and enlightens us about the hidden, core nature of the work that enticed us in the first place. We find that all along, we had what we needed from the beginning and that in the end we have returned to its essence, an essence we could not understand until we had undertaken the journey.”

David mentions vocation, here. In recent times, vocation has become domesticated into mere occupation of ‘career’. But dust aside these superficial trappings and vocation is revealed to be something far deeper—something more akin to a ‘calling’ or ‘summoning’.

Whether we heed the calling or not is a different question. And there is so much in this current paradigm that can ‘crowd out’ the call. Productivity, dollars, likes—whatever satiates our manufactured insecurities.

I’ve written about why we must treat all metrics with healthy scepticism. Most are vanity metrics; delusions of progress. They distract and distort our ability to sense and know value.

Ursula K. Le Guin wrote of this in The Dispossessed: An Ambiguous Utopia.

“A child free from the guilt of ownership and the burden of economic competition will grow up with the will to do what needs doing and the capacity for joy in doing it. It is useless work that darkens the heart. The delight of the nursing mother, of the scholar, of the successful hunter, of the good cook, of the skilful maker, of anyone doing needed work and doing it well—this durable joy is perhaps the deepest source of human affection and of sociality as a whole.”

This passage may seem heretically socialist of me to share. Seemingly hypocritical, too, given my love of fine tailoring and whisky.[^ Seemingly—yet not. Markets and pleasures like these existed long before the prevailing paradigm of capitalism.] My point here is not so much a political one.[^ Yet nothing is not political.] Rather, I want to help dispel the illusions that distract us and keep us small. It is useless work that darkens the heart.

I’ve met many an entrepreneur and executive that haven’t yet heeded the call, and haven’t yet arrived into a life chapter of ‘post-achievement’[^ By this I mean: you have attained conventional explicit success and/or realised its fundamental hollowness, and thus are ready to pursue something beyond yourself.]—nor the window of disenchantment that often follows any significant ‘success’. Are they happy, satisfied and fulfilled, with a deep sense of eudaemonia? Sometimes, yes! Though I’m not always so sure.

There’s another passage about ambition from David Whyte’s Consolations[^ I feel bad for the amount I have lifted for this musing here, but I trust David will be okay with this.] that speaks to this.

“Ambition is natural to the first steps of youth who must experience its essential falsity to know the larger reality that stands behind it, but held onto too long, and especially in eldership, it always comes to lack surprise, turns the last years of the ambitious into a second childhood, and makes the once successful into an object of pity.”

Exquisite burn there, David; deftly done. And also: a point well made. There’s a discernible difference between those of us who have awakened (or are in the dark forest of awakening) to our ‘calling’, and those of us who have yet to.[^ This is not quite the glint of an infinite player, as heeding the call can be quite heavy and solemn. But it gestures towards a similar horizon.]

I should add: there’s a danger in naming one’s calling, too. To define and declare a pithy personal purpose statement is akin to the ‘very disease of ambition’ that David Whyte wrote of, earlier. The fact that it can be so very easy to explain to others. The power and peril of Naming is also something Simon van der Els and I spoke of, too. And it’s something David Whyte conveys in All the True Vows:

All the true vows
are secret vows
the ones we speak out loud
are the ones we break.

The nebulous point I am trying to make here is that: there is a thread to follow. A calling to attend to—if we know how to listen. It might be but an inkling or velleity, a faint stirring or persistent hunch. But—it’s there. And your calling will keep calling, as Michael Meade says.

On enactment

By the fire, under the stars, after the dinner hosted by my wonderful client, I found myself in a contemplative moment. One of the executive attendees came to me and shared how they have been subscribed to the museletter for years, and how they appreciate my subversive posts on LinkedIn and Instagram.[^ I’m always delightfully surprised to meet a subscriber in The Real.] All I know is that I use LinkedIn and Instagram without much strategy or thought. It’s one of my main tensions, these days.

Every time I go onto the platforms, I witness the ongoing genocide of the Palestinian people. I now see images of starved and skeletal children, followed by blatant lies and outright denial by prominent voices and those in positions of power. The algorithms think I want to see more of this content. I don’t, it’s horrifying. I feel moved to talk about it, to not look away, even though my heart can barely take it any more. Add to this the ICE raids, the callous abandoning of climate targets, the dismantling of civil liberties, and the threatening decline into fascism, and, well—it makes any of us question what we are doing.[^ As ever, there remains the hope-beyond-hope. The way we will overcorrect for this terrible chapter will be glorious (and then not).]

Suffice to say: I remain so easily triggered by what’s happening in our world. I act and share posts without much thought (though of course it always feels as though I am not doing enough). I feel bad for wanting to also share nice things (which I know is important, yet still: I feel bad). I feel bad centring myself in this post, even now. And then I feel bad for feeling bad. It’s a wretched cycle. And yet somehow we must participate in it all.

The person whomst I was in discussion with that night shared much the same tangle of wretchedness. Coupled with the sense of responsibility that comes from being an executive in a large organisation. I wanted them to know that their influence is non-zero.

There’s always the question of what to do. I remember a client once told me that they had, many times, considered leaving their organisation. But then they knew that the place would become overrun by toxicity once they left. It takes more energy to build/grow (negative entropy) than it does to destroy/decompose (entropy). And besides, they were proud of the many tweaks they have achieved to move the organisation towards something more wholesome. Tweaks that most wouldn’t notice—but they knew that they were sowing myriad subtle significances.

The allure of ‘escape’ is there for all of us. A retreat to something simpler.

This could be your calling. Kim and I recently attended the premier of The New Peasants and such a life is mighty tempting. I yearn to have such neighbours.

But the temptation of escape can also be a siren call to allure us into distraction. Like a will o’ the wisp, escape might be a false light leading us astray.

How do we discern the difference between siren-song of escape and that which might be our true calling? I don’t know.

Ha, I really don’t. But it’s an enlivening question. I wish I could tell you how <— but actually, I don’t. For if I could tell you, it wouldn’t be your path.

“How do you know that you’re on your path?” David Whyte asks, 13 years ago. “Because it disappears. That’s how you know.”

The sleeper agents I know and love working with—heck, all the folk I love being with—are staying with the trouble. Amidst all the consternation, frustration and doubt, there’s a part within each of them—however quiet—that knows they are exactly where they need to be.

The one thing I would say, though, is that whilst we might each move quietly and plant things—there will also come a time where you feel the kairos of your moment. The proper time for more than subtly-significant action. A propitious time in which you no longer play the role of sleeper agent—but a role in which you enact your agency proper. Because we can’t pretend to be asleep forever.

On living mythically

To live mythically is to not centre yourself as the hero, nor to fancy yourself the only ‘player character’ in a world of non-player characters. We all have our parts to play in this grand pantomime.

A key is in the attunement. It’s in the receptivity to the myriad subtle moments in which we can enact the role we are called to play.

But as I conclude this museletter, I note some interesting tensions within me.

Part of me appreciates the role of tactical cowardice in service to strategic courage. We might call this slyness, guile, or cunning. Not the most noble qualities, I know. But quintessentially fox-like. (I might have alluded to this in my post The Lions Are Back). So, whilst I hint at big action—I don’t want you to blow your cover. But at the same time another part of me wants us all to rise up! We are on a terrible trajectory here—enough’s enough.

So, uh, continue to move quietly and plant things, but... maybe do it a little more bigly.

Because I want for all of us to be better able to recognise our moment when they arrive. To “Be big. Not for ego, but for the sake of what matters most,” as Gabrielle Feather writes.

Here is an excerpt from her post that on reclaiming purpose beyond productivity, ambition and scale.[^ In this piece I reference Gabrielle Feather, who references Jess Serrante, who references Joanna Macy. What a wondrous thread.] She aptly articulates the kairos of this epoch we share, and gifts us with the perfect two sentences with which to conclude this post.

Jess Serrante, a student of Joanna Macy (who is currently in hospice care), recently shared a beautiful and timely anecdote from their time together. Joanna’s life and work have shaped a generation of activists, ecophilosophers, and seekers, and her influence is being amplified in these tender days of her transition.

Jess recalls speaking to Joanna during a moment of doubt, struggling to accept praise for their joint podcast We Are The Great Turning. Overwhelmed by imposter syndrome, she confessed her discomfort. Joanna’s response was characteristically clear: “Jess, your only job is to take all of the power or influence that folks might want to give you and use it in service of the Great Turning.”

When I read that line, it was like the final piece of the puzzle fell in place. In her fiercely compassionate way, Joanna was saying: let go of self-doubt. Don’t cling to your smallness. You are needed. Be big. Not for ego, but for the sake of what matters most.

This, too, is dharma. Not the pursuit of significance, but the acceptance of it when it comes, and the commitment to use it well. Many of us (especially those socialised into humility, or shame) fear taking up too much space or losing touch with our good intentions. But as Jess writes, “This time, when the world is burning, is no time for us to choose smallness.” If we’re given energy, love, resources, or recognition, the dharmic path asks that we channel it into service and into something regenerative.

Don’t cling to your smallness. You are needed. Be big.

Warmth,
—fw