Playing the fool in business and markets

John Elkington

The power of the Fool and Jester—even sometimes of the Trickster—was about licensed transgression, a formally sanctioned role that could say the unsayable precisely because it arrived wrapped in absurdity. The caps worn by the Fool and Jester afforded a kind of diplomatic immunity for inconvenient truths.

Intriguingly, yesterday’s edition of The Times had a story on its front page titled: “Even unfunny jokes can give you the last laugh at work.” Researchers tracked the use of humour across 531 talks at 14 biology-related conferences. These were highly technical presentations, with two-fifths of the speakers making no attempt to be playful. Of the 870 jokes attempted, “two-thirds fell flat or landed mildly, earning mostly quiet chuckles.”

I don’t tell jokes, in work or elsewhere, relying instead on situational humour. But I found it interesting that whole-room laughter followed fewer than one in ten jokes. More interesting still, it turned out that men were more likely to use humour, “telling about a third more jokes than women, and enjoying a ’10 per cent high probability of eliciting laughter’.”

I have long sensed that it is harder for women to play this role—indeed, historically, I suspect it was passing rare for a woman to occupy the Jester’s role. For long. And if the role is still gendered today, a key question is what it would take for women to come out on top in this field?

In any event, whether assumed by men or women, the role hasn’t disappeared. Instead, it has migrated, fragmented, and gone partly underground in modern institutions. Before exploring its modern equivalents, though, let’s consider some of the mechanics that made the Jester effective:

• Emotional disarmament—laughter lowers defences while the real point lands
• Pattern recognition out loud—comedy is essentially calling out the gap between what is and what’s claimed
• Plausible deniability—”I’m only joking” creates an escape hatch for both speaker and listener
• No career stake in the official story—the Fool had nothing to protect, so could see more clearly
• Ritual context—everyone understood the rules of the game, so the Jester could push further than anyone else.

In politics, the spirit of the Jester lives on in TV shows like Yes Minister, The Daily Show, or Armando Iannucci’s work (The Thick of It, Veep). They have done genuine political work—not just by lampooning power but by making visible the absurd gap between public language and private behaviour.

Politicians have admitted changing positions partly to avoid becoming punchlines. That’s real influence.

In business, some organisations now formally embed this function through “red teams,” designated devil’s advocates, or the Japanese concept of metsuke (a watchful eye outside the hierarchy). What’s rarely acknowledged is that these roles work best when they involve genuine wit.

The Fool’s most powerful move was feigned innocence—asking the question everyone knew the answer to, but nobody would say. “Forgive me, I’m just a Fool, but… why do we do it this way again?” In modern decision-making, this is underused to an extraordinary degree. The most dangerous question in any meeting is the genuinely simple one that exposes that nobody knows why the policy exists.

Those who have studied the use of humour in such settings have flagged a number of key elements:

1. Permission to disagree: In high-stakes, hierarchical rooms, a well-placed joke can normalise dissent. Once someone has laughed at the emperor’s new clothes, it becomes slightly easier for the next person to say they can’t see them either.
2. The reframe: Humour reframes faster than argument. Calling something by a different name—the right unexpected name—can shift a room’s entire orientation toward a problem in seconds. Maybe that’s why good speechwriters are often frustrated comedians?
3. The absurdity mirror: Exaggerating a policy or proposal to its logical extreme—not to mock it, but to help reveal its hidden assumptions. If a rule sounds ridiculous at scale, that’s information. Good facilitators do this instinctively.
4. The valve that releases pressure: Not all institutional humour is subversive—some is just tension management. But even that serves a function: it keeps people in the room, keeps the conversation human, and prevents the kind of defensive rigidity that makes real deliberation impossible.
5. Timing as truth-telling: Comedy is fundamentally about timing—and so is good decision-making. The Jester who laughed at the right moment was pointing at something: maybe the pomposity, the pretension, the denial. In a meeting, a well-timed intervention can mark exactly where the group is lying to itself.

Theat said, the Jester function can go wrong in many different ways. Among them:

The lone voice problem—the original Jester had institutional protection. The modern whistleblower-as-wit often doesn’t. Being funny about power is much safer with an audience than in a face-to-face performance review.

Co-option—court Jesters who got too comfortable became entertainers, not truth-tellers. The same happens when “culture” and “banter” become a way of defusing legitimate criticism rather than hearing it.

Punching down—humour that mocks the powerless while flattering the powerful inverts the whole function. Much corporate “fun” does exactly this.

The laugh that ends the conversation—sometimes a joke is deployed to close down a difficult question rather than open it. This is the anti-Jester move, and it’s worth watching for.

Despite the possible reverses, what the best Jesters understood—and modern institutions mostly forget—is that seriousness is not the same as truth-telling. In fact, excessive seriousness is often a defence mechanism: the gravity of proceedings can become a tool for suppressing inconvenient reality.

The gift of the Fool and the Jester was a kind of ruthless clarity dressed up as nonsense. And the most honest question any organisation can ask itself is: Who plays that role here, and are we listening to them? If the answer is nobody, it’s a warning sign.

So how do Fools and Jesters play into markets? First, it’s worth recalling that markets are stories we tell ourselves, embedded in social structures. They’re not neutral price-discovery mechanisms—they’re belief systems coupled with power hierarchies. There are dominant narratives (the “house view”), high priests (central bankers, major analysts, ratings agencies), courtiers (aplenty), and enormous social pressure to speak the official language.

The Jester function isn’t just possible in markets—it’s structurally necessary, and periodically explosive when it finally arrives. So, what are some examples of market Tomfoolery?

This creates a systematic suppression of the Jester function. The incentive structures of institutional finance—career risk, benchmarking, quarterly performance—all push us toward consensus. The cost of being wrong with everyone is much lower than the cost of being right alone. So, the Jester gets fired, the position is closed, and the court continues until it can’t.

Now for a few more examples to underscore the critically important role of market oddballs:

1. The heterodox analyst: Every now and then, someone inside a major institution publishes a note that says, essentially, “this is all nonsense.” Sometimes it’s dressed up carefully; sometimes it isn’t. These notes circulate virally precisely because they’re doing Jester work—giving voice to what traders are muttering privately but won’t say on the record. The analyst has briefly put on the Fool’s cap.
2. Financial Fools: This is genuinely interesting as a structural phenomenon. Anonymous or semi-anonymous accounts with names like “Macro Alf” or accounts that run pure absurdist market commentary have acquired genuine influence—partly because of their distance from institutional seriousness. The pseudonym is the modern Fool’s cap. It licenses a kind of bluntness that a named institutional voice cannot afford.
3. The earnings call questioner: Occasionally, on an earnings call, someone asks the question nobody in the room wants asked. It usually lands with an almost physical awkwardness—you can hear the executive recalibrate in real time. That moment of awkward silence is the Jester’s laugh landing. These questioners rarely get invited back, which tells you everything about how the market court feels about the function.
4. The meme stock phenomenon: GameStop in 2021 was, among other things, a genuinely Jester-like event. A crowd of retail investors on Reddit—operating in an explicitly absurdist, ironic register—exposed and then exploited the naked short positions of major hedge funds. The language was deliberately ridiculous: “tendies,” “to the moon,” “stonks.” The foolishness was the point. It created plausible deniability, community cohesion, and—crucially—it named something true: that markets are a game with different rules for different players, and that the serious language of finance is partly a legitimating costume.
5. The maverick economist: Figures like Hyman Minsky, Nouriel Roubini pre-2008, or Steve Keen occupy a Jester-adjacent role in economic discourse—not because they’re funny, but because they are structurally positioned as the voice saying “this will end badly” while the court insists on stability. Minsky’s entire theory is essentially a formalisation of the Jester’s insight: stability breeds instability, or in court terms, the more convinced the king is of his own wisdom, the closer he is to catastrophe.

Smart risk managers watch what is going on around them—and listen to the jokes.

How can we capture the spirit of the Fool, Jester or even Trickster (the most disruptive of the three) and infuse it into market mechanisms? A few markets and institutions have already experimented with approaches like:

Red team investing—dedicated teams whose job is to argue against the house position

Pre-mortem analysis—imagining the investment has failed and working backwards (structured absurdism)

Anonymous idea submission—removing hierarchy from the pitch process so junior voices can say what seniors won’t

Scenario planning with deliberately ridiculous scenarios—forcing the room to take seriously what it would normally laugh off.

But here’s the catch, and it’s the same catch as in every court: the institutionalised Jester can quickly lose the Jester function. The moment the fool is on the organisation chart, the court knows how to manage him. The power of the role has always come from its marginality, its outsiderness, its willingness to have nothing to lose.

Homeward bound: social signalling on my train back to Euston (source: JE, 2026)

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This is a summary of an article by John Elkington, whose book *Green Swans* was published by Scala Publishing, originally published on 20 March 2026 on Substack—a digital publishing platform of the same name that enables authors, journalists and content creators to publish subscription-based email newsletters, articles, podcasts and videos and earn money directly from their audiences.