This chapter focuses on five personas sketched as caricatures—the sentinel, artist, designer, hacker and subversive bureaucrat—that should ideally be enrolled in some kinds of epistemic communities in order to hold and activate the profound tensions that accompany the dissonant times. These caricatures are a rhetorical device to foreground the diverse, tension-filled sensibilities and skills that must accompany radical urban politics and play. Sentinels give the conceptual and emotional stuffing to engage in anticipatory thinking because grounded interventions to bring light and possibility into the city cannot arise without a line of sight on the future. Artistic processes produce a form of knowledge and experience that helps one to learn how to inhabit complexity, uncertainty, paradox, pain, love, fear and many other waves of emotional intensity. At his or her core, a hacker seeks to find ways to rewire code or circuits to achieve an improved or extended or alternative outcome than intended by the system designers.