Previous research has examined how mobility and career competencies influence success in boundaryless careers. In this study, we flip the direction of those relationships and we explore how the interplay between success and failure relates to subsequent mobility, career competencies, and career evolution through the life span. Using a biographical design, we conceptualize success and failure as critical moments that influence the unfolding of the boundaryless careers of Oscar-nominated film directors. While the dominant metaphors of boundaryless careers are those of “paths,” “ladders,” “trajectories,” and “plateaus,” our findings suggest a new metaphor: the roller coaster.