This conversation explores unschooling through theory and personal experience of Astra Taylor, who examines deschooling alongside the continua of Freedom/Oppression, Personal Control/Personal Autonomy, Solitude/Boredom, Privilege/Social Reproduction, Socialisation/Democracy. Taylor reveals complex relationships between the main strands of her work: film-making and activism. She analyses the dual nature of the contemporary university, and defines it as a place of oppression and freedom. Taylor explains own preference for activism over academic work, talks about her involvement in Occupy Wall Street Movement, and describes her experience as one of the founders of the Rolling Jubilee campaign. Taylor moves on to argue that there is a need to augment traditional trade unions in the US, and introduces an alternative organization called the Debt Collective. In her analyses Taylor pays particular attention to digital media, which serve as important vehicles for her activism. It is here that she develops a sophisticated theory of cultural work in the digital context, the rising tensions between amateurs and professionals, market-oriented platforms for social networking, and political economy of digital work including but not limited to personal branding. Finally, Taylor shows that contemporary social movements have a lot to learn from their historical counterparts, links the past and the present of activism, and asserts that the contemporary left is going to have to refight some old battles on the new networked terrain.