The domain of (job) performance has evolved to include organizational citizenship behaviors (OCB) and deviant or counter-productive behaviors (CWB), in addition to task-related behaviors. This chapter discusses the significance of task, citizenship, and counterproductive performance behaviors for sustainable career development in organizational settings. We focus on OCB and CWB behaviors as these behaviors are likely to be learned early in one’s career and to persist. Additionally, such behaviors learned in one domain may spill over to another domain. We show that cheating behaviors and reporting cheating in academic settings manifest in the form of CWB and OCB in organizational settings. After reviewing research on OCB and CWB focusing on antecedent behaviors common to each, we review academic integrity research that focused on personality as antecedents of academic misconduct. Next, these streams of research are integrated to argue that personality variables (adjustment, prudence and likeability), and behavioral samples (reporting cheating and cheating behavior) from one domain (academic world) could be useful predictors of desirable (OCB) and undesirable (CWB) behaviors in another domain. We then describe a study investigating our predictions. Finally, we discuss implications of study results for career theory and practice, and offer suggestions for future research.