Documentary series following filmmaker John Wilson as he begins a journey of self-discovery by observing the cultures, communities, and societies of New York, following everyday citizens as they go about their daily lives, and offering them advice where needed. With his wry narration and comedic perspective, the series serves as a portrayal of Wilson's wild imagination and his outlook on this unique city. Each episode in the six-part series follows a different theme, such as "How To Put Up Scaffolding", "How To Make Small Talk", and "How To Split the Check".