What is criticality? What does it mean to think beyond conventional perspectives? Under what conditions do students learn to question power structures and explore alternative possibilities? Criticality provides the ability to analyze, synthesize, and evaluate ideas when imagining the possible, both “what exists” and “what could be.” It encompasses cognitive variables related to interpretation, analysis, evaluation, and self-regulation, as well as dispositional variables or mental habits. The willingness to reconsider ideas from different perspectives is fundamental for the analysis and evaluation of ethics, to become aware that what is possible is political, and to raise awareness about who in society has the right to discover new possibilities and who is denied that right. Criticality is essential for deep, reflective learning as it encourages students to process information, analyze complex issues, consider different perspectives, solve problems, examine assumptions, explore implications and consequences, and accept contradictions and inconsistencies in their own thinking and experience. One of the key challenges facing education in the twenty-first century is teaching students criticality. To address this challenge, we must understand what it means to think and reason critically and intentionally while identifying specific strategies that encourage transcending conventional perspectives.