Fear of failure is examined from a need achievement perspective and in the context of research amongst high school and university students. Theory and data suggest that fear of failure can be separated into two camps: overstriving and self-protection. Although each has yields in terms of achievement or in terms of self-protection, they render the academic process an uncertain one for students marked by anxiety, low resilience, and vulnerability to learned helplessness. A cascading model of failure avoidance is developed that differentiates various aspects of fear of failure on the basis of a number of correlates and outcomes and provides direction for intervention. An alternative orientation—success orientation—is explored in detail as are four factors identified as the key means to promote success orientation. These factors are self-belief, control, learning focus, and value of school and ways to promote these in the educational and counselling context are discussed.