We continue our pilgrimage into jesterhood
Last week I introduced the idea of the Jester with a Hundred Faces — not a performer, not a clown, but an archetype of insight, truth-telling, and strategic conscience.
This week, we go deeper. We explore why this archetype is re-emerging now, how it manifests in contemporary organisations, and what forms a modern jester can take. Because in the volatility, uncertainty, complexity and ambiguity of our Postnormal Era* — where the old rules no longer apply — it’s the jester, not the conventional hero, who may guide us through.
Why We Overlooked the Jester for So Long
Despite their deep historical importance, jesters have been astonishingly under-researched. For most of the modern era, they were treated as court curiosities — colourful footnotes, not organisational assets. Yet weak signals across research and practice indicate that this role is returning. Let’s check them.
Some pioneers saw this long before the current awakening. Beatrice Otto documented the universality of jesters across civilisations and highlighted their governance value as “outsiders on the inside” — trusted truth-tellers disguised in licensed folly. David Firth & Alan Leigh proposed the “Corporate Fool” back in 1998, recognising the need for sanctioned mavericks in organisational life.
These early sparks are now being matched by modern emergence signals:
Elfenbein & Elfenbein (2025)
Their recent research shows that integral humour — when used deliberately — creates informal informational infrastructure inside organisations. In practice, this means:
- honest backchannels,
- safer truth-telling,
- faster insight,
- and a softening of hierarchical fear. They describe the functions of a jester without ever naming the archetype — and their historical frame remains limited to British jester traditions.
The Dutch NarrenGilde (2022 – )
A practitioner-led guild of organisational jesters who actively challenge groupthink and deliver ‘the license to speak truth’ with a certificate. A living experiment in modern jesterhood — emergent, but unmistakably the right shape.
My Own Work (2024- )
Through my research for Serendipity Unleashed – Hidden Wisdom of the Jesters, an unexpected convergence appeared between:
- Arthur Koestler’s bisociation, which he introduces in his brilliant The Act of Creation
- authentic serendipity, my insightful new coinage of true lessons learnt from Persian fairytale Peregrinaggio di tre giovani figliuoli del re di Serendippo
- Gary Klein’s excellent findings in his Seeing What Others Don’t -The Remarkable Ways We Gain Insights, and
- the forgotten role of the historical court jester as a master of the Postnormal Era, To understand the forgotten role of the historical court jester — a figure remarkably well-suited to Postnormal conditions — I undertook a far broader inquiry, spanning multiple civilisations and a timeline from 700 BC to 1790. This wider lens revealed structural patterns that isolated British accounts could not capture.
I found that jesters were not entertainers — that role belonged to fools. Jesters were highly respected advisors at court: structured creators of insight, masters of bisociation, deliberately disturbing habitual thought to open new pathways. A widely misunderstood archetype, often blurred together with the ‘fool’, even though their functions were entirely different.
I found that jesters were not entertainers — that role belonged to fools.
And crucially: this forgotten archetype is exactly what contemporary organisations now need.
Together, these signals tell a simple story: The jester’s return is not nostalgia — it is structural necessity. And its re-emergence has already begun.
The Three Emerging Archetypes of the 21st-Century Jester
As various researchers catalogue jester roles — Firth’s ten, Hoedemakers’ sixteen, Elfenbein’s emerging insight functions — it becomes clear that the modern jester is not a single role but a spectrum of organisational roles.
To make this usable, I propose in my forthcoming book a new practical taxonomy: three archetypes based not on theatrical traits but on organisational arenas and forms of value.
1. The Challenger of Power
Core energy: Strategic truth-telling, ethical accountability Primary arena: Corporations, governments, fragile democracies
This jester confronts blind spots at the top. He speaks the truth that others avoid, restores moral clarity, and prevents self-inflicted disasters. Tom Hagen belongs here. Stańczyk belongs here. Every serious conscience figure in leadership history belongs here.
2. The Catalyst of Creativity
Core energy: Innovation through tension and play Primary arena: Ecosystems, innovation labs, creative hubs
This jester breaks stale patterns, dissolves rigid mental models and provokes bisociation — Koestler’s collision of independent matrices that produces insight. Where teams become too polite, too certain or too linear, he reintroduces ambiguity as fuel for creativity.
3. The Weaver of Meaning
Core energy: Sensemaking, narrative creation, shared understanding Primary arena: Communities, networks, post-crisis teams
This jester translates complexity into coherence. He makes hidden tensions visible, constructs new meaning and helps groups integrate what they cannot yet articulate. He also masters one of the rarest skills in organisational life: separating what is salient — attention-grabbing — from what is genuinely relevant. Elfenbein’s backchannel communicator sits here — a subtle but crucial function.
Closing Reflection
A world shaped by uncertainty cannot rely on roles built for stability. The Postnormal Era demands figures who can navigate ambiguity, challenge illusions, ignite insight and restore the moral compass of organisations.
The jester — long dismissed as a relic — may be the archetype our times need most.
And as we continue our peregrinaggio into this forgotten lineage, one truth keeps emerging:
It’s not what the jester is. It’s what the jester does.
And what the 21st-Century Jester does —challenge power, catalyze insight, restore meaning —is exactly what our Postnormal Era now demands.
What kind of ideas does this spark? Did you know the difference between a jester and a fool.?
*NOTE: For Postnormal Era check Serendipitor’s blog from August 2014 – it includes the original table “Normal Era vs Postnormal Era”. The table has since been slightly modified and updated, the latest version is in my book chapter
