Surgical education is in the process of tumultuous change. Mastering this change will require a new set of competencies and a new understanding of the medical education process. While accreditation agencies are rapidly working to define the new criteria and benchmarks, training programs are quickly pulling together curricula, objectives, and evaluation tools. Yet much has already been learned in other complex, high-risk activities. Blue water sailing, ocean racing, and trans-Atlantic crossing are all activities that require a renewed form of leadership and an understanding of how knowledge, skill, and behavior come together to define the competent sailor. Ideas learned in such endeavors may assist the surgical educator in defining the horizons and the hazards of this uncharted voyage.