In most medical schools and residency programs, little or no attention is given to fostering learners' reflection or self-assessment. Yet learners who do not value or who are not effective at these skills are unlikely to extract the maximum benefit from their education. They are at risk of becoming unsafe physicians. To be optimally helpful, teachers need access to the diagnostic information about learners that is provided by their reflections and self-assessments. There are major barriers to learners being reflective and self-assessing. Medicine is dominated by unreflective doing. In the fiercely competitive environment of many teaching programs, many learners correctly perceive that it is unsafe to reveal their fears and deficiencies. Learners often retain this cautious posture even after moving to programs where it is unnecessary. Many learners and teachers have grown accustomed to authoritarian educational approaches in which teachers decide what the learners need and unilaterally evaluate their performance. In this review of the available literature, we summarize the compelling reasons for fostering reflection and self-assessment and for helping learners become their own coaches. Specific strategies and tools for creating programs that foster these values and activities are presented.