I Asked My (Dead) Writers Roundtable to Critique My Newsletter

Behind the scenes of "The Paradox of Brilliant Decision Making"

I just published a newsletter about why smart people make catastrophic decisions. The thesis: wisdom emerges from structures that manufacture doubt — not from individual brilliance.

Then I realized I should eat my own dogfood (practice what I preach).

So I ran my draft through a roundtable of AI personas — each bringing different intellectual traditions, each with contrasting perspectives on what makes writing work.

The writers on my red team:

• Socrates (facilitator, annoyingly good at asking questions)

• Edgar Allan Poe (unity of effect, psychological engineering)

• Henry James (trust the reader's intelligence, collaborative discovery)

• Arthur Schopenhauer (pessimist, no patience for vanity)

• Bharata Muni (ancient Indian aesthetics, emotional transformation)

• Horace (Roman poet, practical craft)

• Aristotle (logos, pathos, ethos—the whole system)

What followed was the “ExComm” experience.

They Disagreed A Lot.

My opening line was: "Smart people make catastrophic decisions."

Poe hated it.

"You have revealed the ghost before the reader has felt the chill. You've given them the answer before they have truly felt the problem's weight."

His suggested fix: Start with the horror. "April 1961. The same president who would save the world eighteen months later authorized an invasion so catastrophically bungled it became a national humiliation."

I pushed back. My audience is busy executives. They need to know what they will gain before they invest time.

Poe adjusted:

"The opening must simultaneously disturb and promise relief. The promise must be present, but it must not eliminate the productive anxiety that drives engagement."

I liked the argument, but was not sure what to do with it.

Then Schopenhauer Pulled No Punches

Schopenhauer was not here to blow smoke up my... When I shared my full draft, he said:

"You have written an essay when you promised a revelation. Your executives will read this and think, 'Yes, groupthink is bad, diverse perspectives are good'—and they will learn nothing they did not already believe they knew."

This hit hard.

But then I explained my actual strategy: “Will not those already feeling the risk at some level automatically audit their own decision-making against these principles?”

Schopenhauer paused. Then:

"This changes everything…. You are not manipulating or inviting discovery — you are arming allies who already recognize the enemy."

He got it. And then he suggested:

"Perhaps after your opening about JFK, you need one sentence that acknowledges their present pain: 'If you've watched a team of intelligent people march confidently toward disaster while you remained silent, you already know this feeling.'"

While I got this, I felt like Schopenhauer was underestimating my reader — if there will be any.

The Ancient Sage Asked the Hardest Question

Bharata Muni's framework comes from the Natyashastra—a 2,000-year-old treatise on Indian performance arts. He asked something no one else did:

"What is the ultimate emotional state you wish your reader to experience — not intellectually comprehend, but viscerally feel — when they finish your piece?"

I said: "The desire for guidance. A guide to help them transform." The value that my platform offers.

He pushed harder:

"Your narrative presents Kennedy's journey masterfully. But the emotional journey remains Kennedy's, not the reader's. The reader observes his transformation but does not experience their own potential for it."

He was right. My mirror was there — I thought  — but it wasn't positioned so readers could see their situation in it.

Horace Fixed the Timing (Like Seward did for Lincoln)

The debate kept circling: Should I explicitly tell readers "this is about you"? Or trust them to figure it out?

Horace, the Roman poet, cut through it:

"Your executives are not fools, but neither are they leisured philosophers with time to contemplate. The explicit connection is not an insult to their intelligence; it is a courtesy that respects their constraints."

But, and this was crucial, he said where matters:

"Let them see Kennedy's failure, understand the mechanism, witness the transformation. Then, in your conclusion, make the connection explicit. Because they have already done the intellectual work. Now you are simply confirming what they have begun to suspect about themselves. This feels like validation of their insight, not lecturing."

Timing. Not just what to say, but when.

The Meta-Moment

At the end, Socrates asked what I'd learned.

I said: "Wise writing, like any decision-making, emerges from the dialectic."

He smiled “with genuine warmth”:

"You've lived the lesson you're teaching."

And that's the point. I wrote a newsletter about how wisdom emerges from structured opposition — from multiple perspectives arguing, testing, refining. Then I used exactly that process to make the piece better.

The AI personas disagreed with each other. Poe wanted psychological engineering; James wanted to trust the reader. Schopenhauer wanted to assault vanity; Bharata wanted emotional architecture. They didn't converge on a single answer. They gave me tensions to navigate.

Which is exactly what Kennedy's ExComm did. And exactly what my newsletter argues every leader needs.

What Actually Changed

After the roundtable, I made three changes:

1. Sharpened the opening to create unease before offering solutions (and subtle mirror)

2. Added an explicit mirror in the conclusion: "If you believe your team is different—Kennedy's team believed this too"

3. Completed "the logical bridge" from Kennedy's story to the reader's situation

Small changes. But they came from friction — from perspectives I would not have generated alone. Contact me if you want to see the full transcript (only about 50 messages).

The Tool

This conversation happened on MyThinkTank.AI — a platform I'm building. The core idea: instead of one AI that gives you "the answer," you get multiple AI perspectives that argue with each other and with you — the most proven wisdom engine in history.

Because the answer isn't the point. The thinking is.

What would the world look like if, in 1962, Kennedy had repeated the typical execute decision-making method that led to the Bay of Pigs disaster? Instead, he built a structure where perspectives collided. That's what saved the world.

It may be just a newsletter, but worth the effort.

Read the newsletter that emerged from this process on LinkedIn: The Paradox of Brilliant Decision-Making