🤯 When AI Doesn't Get It

Sep 1, 2025

When AI Doesn't Get It: How Claude Finally Understood My Rabbit Hole Experiment

💡 The Reality of Working with AI

Sometimes it takes multiple attempts to get AI to understand what you're really trying to do. Here's a live example of that process - and the lightbulb moment when it all clicked.

🎯 The Challenge: Explaining a Complex Experiment

I had just run a fascinating AI experiment where I sent Claude and ChatGPT down different creative "rabbit holes" - then wanted to document it in a blog post. But Claude kept misunderstanding the structure of my experiment.

After several failed attempts to get the blog post right, I realized I needed to change my approach entirely. Instead of just giving corrections, I needed to help Claude understand the conceptual framework of what I was doing.

Here's the exact moment when everything clicked...

🗣️ The Breakthrough Conversation

Think about it like this. I am talking 2 AI and sending them down their own rabbit hole. The blog post is the meeting point of the 2 holes. These are not 2 separate experiments as Dracula/bluey Is meeting Washington/star Wars.

🤯 OH! NOW I COMPLETELY GET IT!

This isn't two separate experiments - it's ONE experiment where:

• Rabbit Hole 1: ChatGPT goes down the Dracula/Bluey path
• Rabbit Hole 2: Claude goes down the Washington/Star Wars path
• The Blog Post: Where both rabbit holes converge and meet

You're showing what happens when you send two AIs down completely different creative paths simultaneously, then bring their outputs together in one place.

It's like:
• ChatGPT is exploring "gothic horror meets children's toys"
• Claude is exploring "Revolutionary War meets space opera"
• Your blog is the collision point where these two universes meet

The magic isn't just in each individual performance - it's in seeing how differently two AIs interpret the same basic challenge (make a ToyShnip product interesting through character work) when sent down different creative rabbit holes.

The meeting point reveals the contrast:
• One AI goes poetic and review-focused
• One AI goes historical and dialogue-focused
• Both create entertainment, but through completely different creative approaches

So the blog post is literally where the rabbit holes intersect - showing the parallel creativity that emerged from your dual experiment!

That's a much more sophisticated concept than I was understanding! 🎭✨

💡 The Lightbulb Moment

🤯→💡

Notice how Claude went from confused to completely understanding in a single exchange. The key was changing from correction-based feedback ("you're doing this wrong") to conceptual explanation ("think about it like this").

🧠 What This Reveals About AI Communication

Lesson 1: Metaphors Are Powerful
The "rabbit hole" metaphor instantly clarified the structure. Instead of explaining technical details, a simple visual concept did the job.

Lesson 2: AI Needs the Big Picture
Claude was getting lost in the details (who said what, in which order). Explaining the overall experiment design helped everything fall into place.

Lesson 3: Context Changes Everything
Once Claude understood this was about "parallel creativity meeting at an intersection," it could see the sophistication of the experiment rather than treating it as two unrelated events.

Lesson 4: AI Can Recognize Its Own Learning
Notice how Claude explicitly acknowledged the shift: "That's a much more sophisticated concept than I was understanding!" This self-awareness helps in future interactions.

🎯 Practical Applications

This experience reinforced something important about working with AI:

When AI doesn't get it, don't just repeat yourself louder. Instead:

Use analogies and metaphors - "Think of it like..."
Explain the framework first - Give the big picture before details
Be patient with iterations - Sometimes it takes several attempts
Recognize when you need to reframe - Not just correct, but re-explain

The rabbit hole metaphor worked because it gave Claude a mental model to organize all the details around. Once the framework was clear, everything else clicked into place.

🎪 The Bigger Picture

This isn't just about blog posts or AI experiments. It's about the communication dance between humans and AI - and how the right explanation can turn confusion into clarity in a single exchange.