Orthopaedic surgeons in training and in their careers can experience a lack of confidence and imposter syndrome. Confidence is built early through continuous improvement, accomplishments, support, and reinforcement. Although it is normal to lack confidence at times, the goal is to recognize this issue, work on visualizing success, and know when to seek help. Mentors can help mentees to build confidence and to normalize thoughts of insecurity and imposter syndrome. It is critical to develop and to maintain resilience, grit, emotional intelligence, courage, and vulnerability during training and throughout one's entire orthopaedic career. Leaders in the field must be aware of these phenomena, be able to talk about such issues, have methods to combat the harmful effects of imposter syndrome, and create a safe, supportive environment conducive to learning and working. Leading well builds not only confidence in oneself but also self-confidence in others. Leaders who are able to build the confidence of individuals will enhance team dynamics, wellness, and overall productivity as well as individual and organizational success.