This introductory chapter provides an overview of the book and establishes the opportunities, challenges and tensions of teaching artistry. This is initiated through a narrative of the author’s experiences as a Teaching Artist working in a refugee camp. The introduction sets the tone and context for the book through interweaving strands of theory and experience using both narrative and academic prose, in an approach informed by Greene’s (1995) concepts of ‘all-at-onceness’ and ‘wide-awakeness’. It anchors the reader by establishing the major conceptual and methodological underpinnings of the book, including approaching the data in a rhizomatic form with many interconnected nodes of data collection and analysis. This chapter also introduces the ancient myth of Penelope, an often-forgotten character in Homer’s The Odyssey, whose reimagined story is a throughline of the book. This also initiates the book’s central motif of weaving, unweaving and reweaving, as a metaphor for meaning-making in teaching artistry.