Purpose: The paper provides initial findings on the causes and consequences of problematic mid‐career work‐role transitions – self‐reported career mistakes described by individuals in terms of a mismatch between expectations and reality. Design/methodology/approach: This exploratory study uses in‐depth interviews based on critical incident technique (CIT) to elicit accounts of problematic work‐role transitions. Findings: Participants reported mismatches arose because their expectations were based on their prior experience, rather than upon information provided by the organisation during the course of the recruitment process. These mismatches stimulated very active sense making on the part of participants, largely focused on finding ways to make their continuation in the role tolerable. Research limitations/implications: The present study, which is exploratory in nature, involved a small sample size, and the use of retrospective accounts. The findings are therefore preliminary and may not be representative of mid‐career managers' experience with problematic work role transitions. However, they confirm the relevance of career mistakes to organisations and individuals and indicate a need for further research on the subject. Practical implications: The study suggested managers moving post in mid‐career bring to their new role a range of expectations based upon prior experience, rather than the recruitment process. Further study is needed, but these findings have significant implications for organisations, in that they suggest recruitment processes must provide information in a manner which might overcome or correct these prior assumptions. Originality/value: The subject of career mistakes has received little treatment in the organisational side of the careers literature, and yet is of everyday concern to organisations and individuals.