In a singularly amusing journey of self-discovery and cultural observation, documentary filmmaker and self-described "anxious New Yorker" John Wilson secretly and obsessively films the lives of his fellow New Yorkers while striving to offer everyday counsel on relatable subjects. Wilson's frank, unpolished comments helps to reconcile modern life's difficult contrasts. Each episode builds on Wilson's previously published "how to" short films, taking radically unexpected turns but remaining grounded in John's refreshing candor.