The growing body of research suggests that leadership is not among the most attractive career goals, especially for the younger work force. However, the need for leadership has not diminished. To shed light on the “problem of supply”, this study addresses the question of why high-potential individuals (i.e., non-leaders) do not pursue leadership positions by focusing on worries about leadership (WAL) and error-related strain. We had two aims: (1) to identify different profiles of WAL among highly educated professionals, and (2) to explore whether their error strain and leadership career intentions differ among the identified WAL profiles. Data were gathered from 955 highly educated Finnish employees representing different sectors. WAL was measured by a three-dimensional scale consisting of worries about failure, work-life imbalance, and harming others. Based on the Latent Profile Analysis, six WAL profiles emerged: (1) Average-WAL (37% of respondents), (2) Low-WAL (34%), (3) High-WAL (6%), (4) Failure-sensitive (9%), (5) Imbalance-sensitive (4%) and (6) Harm-sensitive (11%). Professionals in the Low-WAL profile reported the lowest error strain, whereas employees in the profiles of High-WAL and Failure-sensitive reported the highest error strain. Employees in the Low-WAL profile were more willing to pursue a leadership career in an unfamiliar organization compared to employees in other profiles. In addition, employees within the Low-WAL profile were more willing to pursue a leadership career in an unfamiliar organization compared to their home organization. Implications of our findings and future directions are discussed.