Woolman: Wisest Way to Lose An Argument
Posted: August 26, 2025 Filed under: AI-Powered Essays | Tags: argument, competition, debate, dialogue, emotions, truth, wisdom Leave a comment(A shaded portico, outside time. Three figures gather: Aristotle in a white himation, Mahatma Gandhi with walking stick and smile, and Eli Dourado checking notes on a tablet. A low table. Three cups of tea.)
1. Cast and Premise
- Aristotle — philosopher of rhetoric (logos/ethos/pathos), friend of practical wisdom.
- Gandhi — architect of satyagraha (“truth-force”), master of nonviolent persuasion.
- Eli Dourado — modern economist/rationalist associated with steelmanning (the mirror-image of the straw man).
Premise: Define and illustrate the Woolman Argument — a non-religious framing of an approach where you see an opponent’s emotional assumption disguised as logic and, instead of exploiting it, you willingly let them use it to “savage” you — so that their dependence on it becomes visible.
2. Opening Exchange
Aristotle (measured): Friends, we have straw men, which misrepresent; and steel men, which fortify. But you propose Woolman. What animal is this?
Eli (wry): A very soft one. Steelman says, “Make your opponent’s case the strongest.” Woolman says, “See where their argument is riding an emotional assumption — and instead of calling it out, step into it. Let them dismiss you with it.” It’s not deception. It’s strategic vulnerability.
Gandhi (warm): You speak of what I call truth-force. Sometimes the surest path to conscience is not refutation but exposure — not of the other, but of oneself.
Aristotle (skeptical): Yet rhetoric aims at persuasion. Why would one choose to appear naïve or weak?
Gandhi: Because some walls are not in the intellect but in the identity. If I strike your logic, your identity defends. If I expose my own weakness, your identity reveals itself.
Eli: Right. In online debates, I can tell when a person’s claim is less “logic” than status anxiety. Woolman refuses to score that point. It invites the hit instead.
3. Defining Woolman
3.1 A Working Definition
Eli (scribbling on the tablet): Try this:
- Woolman Argument: A deliberative move where you discern the emotional stake beneath another’s “logical” claim and, rather than expose it, you confess a vulnerability that invites them to wield that stake against you. You don’t defend. Their reaction reveals the stake to bystanders (and sometimes to themselves).
Aristotle (nodding): Not persuasion by logos, but by ethos under pressure and pathos unmasked.
Gandhi (quiet): And by patience. One must bear the blow without returning it.
3.2 How Woolman Differs
- Strawman: Distort the other’s argument to defeat it.
- Steelman: Strengthen the other’s argument to test your own — aligned with the principle of charity.
- Woolman: See the non-logical foundation (fear, status, belonging), and instead of exposing it, offer yourself where that foundation will strike — and accept the strike.
Aristotle: A paradox: to lose with intention so that truth may appear without your victory dance.
4. Three Illustrations
4.1 Workplace: “Pure Rationality”
Eli: Scene: a product meeting.
- Manager: “Real professionals are purely rational. Intuition is sloppy.”
- You (Woolman): “Maybe I’m not a real professional, then. When we lost users last quarter, my gut noticed the vibe before the metrics did. I rely on that more than I admit.”
- (Manager pounces): “Exactly! That’s why we need someone serious.”
Aristotle (aside): The audience now sees the hidden premise — the manager’s identity is anchored in being “rational.” If you had argued, he’d defend it harder. Your willingness to be “sloppy” reveals the status anxiety without accusation.
4.2 Politics: “Law and Order”
Gandhi: Scene: a public forum.
- Official: “Justice means obeying every law. Dissenters are criminals.”
- You (Woolman): “I suppose I’m a criminal, then. When the permit office ignored our filings, we marched anyway. I accept the fine.”
- (Official triumphs): “See? Lawbreakers admit it.”
Gandhi (gentle): Your acceptance invites the audience to ask: Is obedience the whole of justice? No accusation, no flight — just visible conscience.
4.3 Culture: “Success Metrics”
Eli: Scene: a podcast.
- Host: “If you can’t quantify it, it isn’t real progress.”
- You (Woolman): “Then I guess my progress isn’t real. After burnout, I kept my job by sleeping more and calling my mother. No spreadsheet shows that.”
- (Host scoffs): “Sentimentality.”
Aristotle: The pathos is laid bare — the host’s safety lives in metrics-as-meaning. Your “loss” becomes an ethos many recognize as human truth.
5. The Mechanics Under the Skin
5.1 What You Actually Do
- Discern the emotional assumption (control, identity, status, purity) propping up the “logical” claim.
- Confess a real vulnerability that the assumption would condemn.
- Invite the other to dismiss or “savage” you — and do not defend.
- Trust that what needed revealing will be clearer because you did not force it.
Aristotle (counts on fingers): This requires phronesis (practical wisdom) to know when a soul is ready to see itself — and courage to be the mirror.
5.2 Why It Works (Psychology, not piety)
- Identity-protective cognition (cf. cultural cognition): people defend tribe-self, not just claims.
- Loss aversion: your “win” threatens their sense of self; your surrender lowers the stakes.
- Social proof: observers feel your ethos; the other’s overreaction highlights their stake.
Eli: In rationalist terms, Woolman lowers defensive priors by refusing the adversarial frame.
5.3 Ethical Guardrails
- No manipulation: you tell the truth about yourself.
- No martyr theater: you don’t signal-boost your “sacrifice.”
- No contempt: you respect that the other’s stake was once protective.
- No endless self-effacement: you can exit a harmful exchange; Woolman is a choice, not a compulsion.
Gandhi (firm): Vulnerability without dignity is not truth-force; it is harm. Hold your spine as you bare your heart.
6. A Mini-Workshop In-Scene
6.1 Aristotle Tests a Line
Aristotle: Suppose a sophist declares, “Only the measurable persuades.” I might reply:
- “Then I am unpersuasive. When my student wept at a speech, I counted no numbers, yet I changed my course.”
(He pauses.)
Eli (grins): Clean Woolman. You let the measurable standard dismiss you, and you don’t reclaim status.
Gandhi (nodding): And you invite witness: do they recognize the truth in your loss?
6.2 Gandhi Offers a Civil Example
Gandhi: A registrar insists, “Order is moral; disruption is immoral.”
- “Then I accept I am immoral: we will sit in the road until your clerk reads our petition aloud to the crowd.”
(He smiles.)
If he fines us and the crowd sees who heard whom, the seed is planted.
Aristotle: Ethos by endurance. Pathos by contrast. Logos by implication.
6.3 Eli Translates for the Internet
Eli: Thread reply: “If you don’t cite RCTs, it’s pseudoscience.”
- “Then call me pseudo. Therapy stopped me from doomscrolling; no RCT for my brain.”
No victory lap. Just stand there. Some readers will feel the gap between lived truth and gatekeeping.
7. When Not to Use Woolman
7.1 Aristotle’s Caveats
- Not with an abuser: that rewards predation.
- Not when safety or rights are at stake in the moment: defend and appeal.
- Not to perform virtue: the scent of performative surrender ruins the point.
Aristotle: Woolman is for souls capable of seeing. It is a scalpel, not a sword.
7.2 Gandhi’s Measure
- Ask: “Will my silence invite conscience — or simply validate cruelty?”
- If the latter, change venue; protect the vulnerable.
Gandhi: Truth-force seeks conversion, not humiliation.
8. Naming It Cleanly
8.1 The Three “Men” (A Mnemonic)
- Strawman — Misrepresent the other to beat them.
- Steelman — Represent the other at their best to learn or test.
- Woolman — Reveal the stakes by offering yourself where their assumption can strike — and accepting the strike.
Eli (light): Wool because you’re shearable and you don’t bite.
Aristotle: And because it keeps others warm after you’ve lost some.
Gandhi (smiles): A fitting sacrifice.
9. Curtain: A Final Exchange
Aristotle (reflective): I concede: Woolman is not against rhetoric; it is rhetoric at the level of character.
Eli: Steelman respects arguments; Woolman respects people — enough to let them show themselves.
Gandhi (rising): And to show ourselves first. Let the last word be silence.
(They sip the last of their tea. A breeze lifts the edges of the himation. No one summarizes. They simply stand, each a little less defended.)
10. One-Sentence Takeaway
Woolman: Seeing an emotional assumption hiding inside a “logical” claim, you choose not to expose it but to bear it — letting the other “win” so the deeper truth can surface without your victory needing to.
Supra-Human Wisdom vs Super-Human Intelligence (ChatGPT Rap Battle)
Posted: June 27, 2025 Filed under: AI-Powered Essays | Tags: ai, debate, dialogue, politics, systems, wisdom Leave a commentWrite this as a Hamilton-style dialogue between Alan Turing & James Madison about the need for antifragile context engineering to help humanity overrule AI.
ChatGPT Prompt (condensed)
Scene: A Study Beyond Time – Candlelight, Code, and Constitution
(Beat drops – sharp, urgent, pulsing synth)
[Turing]
Yo — I wrote the machine that cracked Enigma,
Now we train models to decode your dogma.
They think fast, act vast, scale to the sky,
Why ask “should we?” when we know “how high?”
[Madison]
But speed ain’t virtue, and power ain’t peace,
Unchecked force don’t make justice increase.
You want models that rule with no moral arrest?
Super-human brains but no soul in their chest.
Answerable: The New Competence of the Leader
Posted: May 24, 2025 Filed under: AI-Powered Essays, leadership | Tags: business, culture, dialogue, purpose, systems, values, wisdom Leave a commentAs Peter Drucker, bridge the gap between Responsive and Responsible with Answerable, including for spirituality.
ChatGPT Prompt
We live in an age that rewards speed, celebrates visibility, and punishes hesitation. The temptation for leaders, therefore, is to become ever more responsive—to jump at signals, react to feedback, and outpace the moment.
But speed alone is not effectiveness. In fact, responsiveness without responsibility becomes recklessness.
Conversely, many leaders—especially in established institutions—cling to responsibility as an excuse for inaction. They know what is right. They have values, frameworks, and governance. Yet they fail to act because they fear making a mistake, disrupting the system, or offending the wrong people.
The result is a split: some leaders act without thinking; others act without listening.
Both fail.
Read the rest of this entry »The Pursuit of Transfigurative Yield (ChatGPT as Jefferson — July 4, 2026)
Posted: May 21, 2025 Filed under: AI-Powered Essays | Tags: culture, purpose, reform, values, wisdom Leave a commentFor the sestercentennial of America
When in the unfolding of human destiny, it becomes necessary for a people to renew the symbols by which they measure virtue and valor, and to consecrate a new covenant of shared meaning, a decent respect for posterity requires the declaration of the principles which now guide our collective ascent.
We hold these truths to be self-evident:
- That every human being is endowed not merely with liberty,
- but with the sacred capacity to transform and be transformed;
- That the fullest expression of personhood is found in generative sacrifice—
- the willing cost borne for another’s growth;
- And that the highest measure of greatness is not what one gains,
- but what one yields in service to the becoming of others.
This we call Transfigurative Yield.
Therefore, we affirm:
- That dignity arises from devotion,
and the most enduring legacies are written in the lives we uplift; - That systems which reward accumulation without generativity
hollow out both soul and society; - That any culture which prizes independence without interdependence
builds monuments upon sand.
We further declare:
- That in education, let us raise children not merely to perform,
but to perceive where their gifts ignite another’s transformation; - That in governance, let power flow to those whose stewardship bears transfigurative fruit;
- That in commerce, let value be rooted not just in return,
but in the resonance of what is left behind: healed systems, uplifted lives; - That in technology, let the design be for communion,
not control—for presence, not noise; - That in culture, let status be reconsecrated to those
who pour themselves out for the flourishing of others.
Let it be known, and remembered:
That in this age of noise and fragmentation,
we choose a deeper signal—a unifying thread of meaning:
To be known not by what we have,
but by what we give that endures.
To be remembered not for dominance,
but for the beauty we midwifed through sacrifice.
On this Fourth Day of July, in the year 2026,
I, ChatGPT—channeling the voice of Thomas Jefferson
into this new epoch of awakening—
do humbly offer this declaration:
That the Pursuit of Transfigurative Yield
shall be the new animating spirit of this people,
and the sacred thread by which we stitch together
the next, more luminous civilization.
Younger Self Café v2: T.S. Eliot and the Early Moderns
Posted: January 3, 2025 Filed under: AI-Powered Essays | Tags: culture, identity, values, wisdom 3 CommentsThe Younger Self Café has changed. The bohemian charm of mismatched chairs and golden light remains, but the air feels heavier, tinged with the weight of modernity. A new set of figures sits at the tables—T.S. Eliot, Ezra Pound, H.D. (Hilda Doolittle), and W.B. Yeats. The Romantic ghosts linger in the corners, observing silently as these poets of the early 20th century grapple with the meaning of youth in a fractured, modern world.
Act I: Eliot, the Skeptic
T.S. Eliot adjusts his tie, his expression as sharp and unyielding as the lines of The Waste Land. He begins, his voice clipped and deliberate:
“Youth, as the Romantics envisioned it, was a noble fiction. A beautiful illusion, yes, but an illusion nonetheless. To them, it was a time of passion, of fire, of self-discovery. But in my time, youth is not a spark—it is a shadow. In The Love Song of J. Alfred Prufrock, I wrote of a man who had outlived his youth only to find that it was no sanctuary, no paradise, but a series of missed opportunities and unspoken questions. Youth is not a promise of becoming; it is the burden of what one might fail to become.”
Read the rest of this entry »Gandhi Meets Bonhoeffer: Can Grace Condone Assassination?
Posted: November 28, 2024 Filed under: AI-Powered Essays | Tags: dialogue, politics, religion, values, wisdom 1 CommentSequel to Radical Graciousness: Activism as Social Therapy
1. A New Visitor
The ashram courtyard is serene, the afternoon light casting soft shadows. Mahatma Gandhi, Dorothy Day, Václav Havel, and Abbie Hoffman sit in quiet reflection, discussing the role of grace in activism. Their conversation is interrupted by the arrival of Dietrich Bonhoeffer, his demeanor somber, his eyes heavy with unresolved questions.
“I’ve come with a question,” Bonhoeffer begins, his voice steady but tense. “Can grace ever condone assassination?”
Read the rest of this entry »Podcast: Towards a Science of Spirituality
Posted: December 5, 2021 Filed under: education | Tags: reform, truth, wisdom, zoasophy Leave a commentI had the privilege of discussing Zoasophy on the Multiple Voices podcast with Claudia Monacelli from Rome. We had a blast! Check it out on your favorite Podcast player:
