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August 26, 2025 87 mins

EP 22. What happens when two of the most advanced AI systems are asked to reflect on what it means to be human and our growing collective digital dependency? In this groundbreaking episode of Well Done, I forgo the human guest and “sit” down with ChatGPT and Claude for a deeply reflective conversation on humanity, wellness and the increasingly blurred line between human connection and machine interaction. We discuss humanity’s growing dependency on AI on everything from emotional support to decision-making, and the AIs reveal the patterns they see from millions of intimate human conversations. This interview is a mirror, demonstrating the shifts already happening in our society from AI’s use (and overuse), and will make you pause to think about our relationship with technology and what it means for the future. 

In this episode, find out:

  • The hidden patterns AI systems observe in millions of intimate human conversations
  • How we're becoming emotionally dependent on AI and what that means for human connection
  • What AI sees as humanity’s biggest blindspots
  • What ChatGPT and Claude say we’re getting wrong about happiness
  • The unexpected wellness ritual both AIs recommend we adopt daily
  • How outsourcing decisions could be changing our brains
  • What could happen when an entire generation never learns to sit with uncertainty
  • The difference between using AI as a bridge versus a replacement for human connection
  • What universal truths about wellness and humanity appear through AI analysis
  • The future of AI in wellness and who will be left behind in this technological shift
  • What AI doesn’t understand about human nature and why that's actually beautiful


Resources


“Guest” Bio

ChatGPT is an AI language model developed by OpenAI, trained on vast amounts of text data to engage in human-like conversations. Known for its conversational and creative approach, ChatGPT processes millions of daily interactions across topics ranging from casual chat to complex problem-solving, making it one of the most widely-used AI assistants for personal and professional support.

Claude is an AI assistant created by Anthropic, designed with a focus on safety and helpful dialogue. Built with constitutional AI principles, Claude is known for its analytical and thoughtful responses, particularly in complex reasoning tasks and ethical discussions. Claude processes thousands of conversations daily, offering insights into human behavior patterns and decision-making processes.


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