In this article, I define self-knowledge and describe how it can serve as a basis for creating contexts for multicultural engagement. The article describes a course where teachers critically reflect on media, biographies, their personal narratives, and professional application projects. Media, biographies, professional application projects, and personal narratives are powerful sources for deepening self-knowledge and for posing critical questions about difference and diversity. Key elements of the course are discussed and four course assignments are described. Comments from teachers are woven throughout the article to illustrate insights that can be gained through critical self-reflection. The article ends with lessons the author learned while teaching about self-knowledge.