Automation, mobile internet, and artificial intelligence are fundamentally upending traditional ideas and cultural norms in regard to nearly every aspect of our contemporary lives. In some ways these technological advancements have helped to improve and enrich our lives, and in other ways these advancements are affecting vast sections of our economy by replacing human labor. Within this body of work, I am investigating labor through the lens of leisure, in order to create a conversation about how sharing one’s leisurely self-interest may become a viable type of gainful employment. In the near future, we will begin to face mass technologic unemployment and it is my aim that this conversation about economics, empathy, technology and automation provides insight to the possibility that our contemporary cultural understanding of “work,” may need to be adjusted.