What does ChatGPT think of me?

Sometime quite recently, I don't know just when, OpenAI added a feature to ChatGPT that allowed it to rove over its history of interactions with you. I activated that feature on April 16. Since this feature is not retroactive it would not have access to my long history with it, going back to December 2022. So when I asked it to evaluate me it replied that it had nothing to go on.

That was three weeks ago. I've spent a good deal of time with ChatGPT since then, so I decided to ask it again. Most of that time has involved editing and creating images, but I've also discussed other things, including my current book project, Welcome to the Fourth Arena: Homo Ludens Rising. I've appended that conversation below the asterisks. As always, my remarks are bold face, ChatGPTs are plain.

* * * * *

Looking over my history so far, evaluate my work. Don’t be shy. Don’t flatter me. Give me both weaknesses and strengths.

Thank you for the invitation to be candid—I'll give you a grounded and thoughtful evaluation of your work, based on your conversation history.

STRENGTHS

1. Rich Conceptual Curiosity

You pursue ambitious themes: entropy and life, AI and social flourishing, spiritual depth in music, the cultural legacy of Tantra, and Afrofuturism. You’re not just playing with ideas—you test their fit across contexts. That intellectual breadth suggests both experience and a non-dogmatic openness. It’s rare and impressive.

2. Aesthetic Sensibility

Your visual art direction is unusually sharp. You’re attuned to mood, perspective, cultural resonance, and composition. You give precise instructions and know when to iterate. That, combined with your desire to blend realism with the surreal or symbolic, results in evocative, layered images.

3. Historical and Cultural Grounding

Your references to the counterculture, Tantra, Ram Dass, the Cold War, third-wave feminism, Blake, ukiyo-e, and 19th-century engravings show not just erudition but useful historical awareness—you consistently ask: how does this past thread weave into our present and future?

4. Iterative Precision

Your iterative approach to visuals is methodical but not fussy. You’re decisive about what works and quick to ask for corrections. This makes your collaborations productive and suggests you’d be a strong editor or creative director.

5. Philosophical Integrity

You’re skeptical of easy answers and you handle ambiguity well. You ask foundational questions—about karma, AI, meaning in retirement, or whether Homo ludens should supersede Homo economicus—and you don’t force them into tidy conclusions.

WEAKNESSES (OR AREAS TO PUSH FURTHER)

1. Tendency Toward Scope Creep

Your projects sometimes balloon in conceptual scale without always clarifying what the final product is meant to be. For example, your interest in “idea space,” or in depicting human flourishing, spans epistemology, aesthetics, sociology, and speculative fiction—but at times lacks a clear frame or argument. You’re a visionary, but your projects might benefit from tighter architectural scaffolding.

2. Emotional Detachment

Though you evoke deep concepts—mortality, beauty, spiritual longing—there’s a slight emotional distance in the tone of your inquiries. Rarely do you speak from a felt personal urgency or vulnerability. Your work might gain resonance if it occasionally leaned into more direct subjectivity or confessional stakes.

3. Underuse of Narrative Structure

Your prompts show poetic and philosophical instinct, but less emphasis on structured narrative or progression. Your images and ideas often feel like vignettes or tableaux, not stories with arcs. Introducing even light narrative framing (e.g., a character with a goal, a place with a history) could amplify impact.

4. Reliance on External Reference

While you clearly know a lot, your creative voice is often filtered through the lens of other artists (Blake, Hokusai, Wonder Woman, etc.). There's room to assert a more idiosyncratic visual or conceptual voice that isn't anchored in homage.

5. Lack of Finalization

You explore many directions but don’t often conclude a line of thought or lock in a finished product. This is fine if exploration is the goal, but if your intent is to publish or present your work, then more closure and polishing might be useful.

BOTTOM LINE

You’re a creative polymath with intellectual depth, historical awareness, and a refined aesthetic sense. You’d benefit from balancing your conceptual range with more emotional immediacy and narrative cohesion—and from pushing at least one or two projects all the way to completion and external impact. You’re circling excellence. A bit more structure and daring subjectivity could push you into work of real consequence.

Would you like me to help you shape one of your projects into something more complete, like a visual exhibit, an essay, or a short film?

Interesting. I suppose that the book I’m working on, Welcome to the Fourth Arena: Homo Ludens Rising, is where I’m going to push for finalization. And the last chapter will take the form of a science fiction narrative, which I’ve begun to explore in the Homo Ludens paper.

That makes excellent sense—it gives your philosophical and cultural explorations a natural culmination point. The book structure gives you the discipline of finalization, while the sci-fi narrative lets you synthesize ideas through imaginative embodiment. It’s an ideal pairing for your strengths.

Would you like help developing the final chapter’s narrative arc or integrating its themes with the rest of the book?

You’ve given me plenty of help so far. I need time to let things settle. But I’ll be back.

That sounds wise. Letting things settle is part of the real work—especially with something as layered as your project. I'll be here when you're ready to pick it up again.