Tori Westerhoff joins Scott to explore the intersection of AI, human psychology, and personal growth. As people increasingly use LLMs for introspection and decision-making, Tori argues that we're missing the diversity of thought that comes from community, even particularly random encounters with strangers. She reveals her own practice: a daily noon reminder to talk to strangers. "If you sycophant yourself, you're never going to grow," she explains. The conversation delves into how LLMs can create echo chambers of thought, and why the randomness of human connection, even just someone on the same bus, helps us update our mental frames and break out of programmed decision-making paradigms.