Documentary filmmaker John Wilson embarks on an odyssey of self-discovery and cultural observation by covertly filming the lives of fellow New Yorkers while trying to share advice. John attempts to give advice while dealing with his own personal issues. The episodes, framed as tutorials and filmed mainly on the streets of New York City, cover topics from small talk to scaffolding. While each episode initially focuses on its title topic, in the course of his investigation, Wilson meets people and strikes up conversations that lead in unpredictable directions.