With a refreshingly punk attitude of irreverence toward hierarchical authority and other cultural conventions, Thinking Critically About What Matters investigates philosophical perspectives from divergent traditions that share a common theme of liberating a person from their own self-centering biases and limited point of view when interpreting the information that comprises reality. The authors, an academic information literacy librarian with a background in philosophy, and an educational consultant and former K-8 teacher, present an actionable approach to critical thinking that will give you the philosophical tools you need to creatively embody these philosophical perspectives in your own life and work. Organized into six chapters, this guide outlines a rebellious attitude for thinking critically about evaluating information, media bias, and information literacy education more broadly; shares practical strategies for sound decision-making and creative thinking in both individual and group contexts; demonstrates how Socrates’ philosophically therapeutic approach can be adapted for critical thinking that’s grounded in intellectual humility, open-mindedness, and frank assessment of one’s values and assumptions about what matters in life; explores Zen Buddhism’s playful, rule-breaking approach to critical thinking, including Bruce Lee’s Taoist admonition to “Be Water,” Buddhism’s invitation to “widen one’s window on oneself and the world” through an emphasis on de-centering the self, and the importance of reflecting on the nature of impermanence; discusses Friedrich Nietzsche’s critique of the hegemony of dominant cultural values as universal “shoulds” and recommends Nietzsche’s “bespoke” theory of practical wisdom centered on positive psychology, self-trust, and individual and group self-expression as a more suitable basis for sound-decision making; culminates in a discussion of intersectional anarchist perspectives on leadership and meaningful work, proposing direct democratic decision-making as a practical framework for inclusive decision-making in teams and organizations; includes extensive artwork and “zine”-style illustrations of philosophical concepts that can serve as the basis for lesson plans, presentations, professional development workshops, or even entire courses on critical thinking; and concludes with reflections on the unique cultural role librarians can play in democratizing information and fostering critical thinking.