For years now career success emerged as one of the focal points in managerial psychology research. It still remains a key topic in contemporary literature. Personality has been identified as an essential predictor of work and career success. In examining associations between personality traits and professional outcomes, the Big Five represents the prevalent theoretical basis. This widely recognized framework stands primarily for bright and affirmative personality attributes. In more recent times, the rather negative side of the personality range received increasing scientific attention, not least triggered by severe scandals in the business world. Especially the Dark Triad personality construct consisting of Machiavellianism, psychopathy and narcissism has attracted growing academic consideration. Surprisingly these rather undesirable personality characteristics do not only promote counterproductive outcomes. Consequently, the two topics of bright as well as dark personality traits and career success constitute the scope of the thesis. To split the topic up and to explore it as sophisticated as possible, a comprehensive scientific approach is required. Supported by a multilayered methodological procedure, the interplay of personality and career success was investigated on heterogeneous criteria: (1) multifaceted bandwidth of personality, (2) diversity of career success indicators, (3) varied decision-making levels, and (4) new work environment. In summary, this dissertation answers the following research questions in three interrelated essays: 1. How successful are both light and dark personalities in terms of objective success criteria? 2. Does a GFP-E specific for executives exist and how is it related to the Dark Triad, success and satisfaction measures? 3. Do paradox personalities, in particular narcissism and humility, succeed in new work environments? The first paper represents the basis for gain in knowledge. It takes a broad attempt by addressing both the bright and dark personality traits of the Big Five and the Dark Triad. Accordingly, the influence of these expansive personality attributes and the selected objective career success indicators budget responsibility and personnel decision-making authority were examined. Empirically, a dual approach with a German sample combining an AI-based automated speech analysis tool with self-reported survey data was chosen. The results indicate a positive relationship between psychopathy and personnel decision-making authority, as well as between narcissism and emotional stability to budget responsibility. In the second article, the interest shifts entirely to the top-management. Here, a narrower personality approach was considered. For this purpose, self-reported survey data from German top-managers were collected. The study demonstrates that a superordinate singular factor (General Factor of Personality, GFP) specifically for executives (GFP-E) exists that is characterized by high agreeableness, extraversion, conscientiousness and openness to experience as well as low neuroticism. Furthermore, the relationship of the GFP-E to the Dark Triad and to success and satisfaction indicators were examined. Positive correlations to these criteria as well as to narcissism were evident. In contrast, negative connections to Machiavellianism and psychopathy were apparent, indicating the existence of a Dark Dyad. Finally, the third essay highlights the impact of paradox personalities on career success, namely the combination of narcissism and humility. In order to reflect the current transformation in the business world, new work settings are integrated in this study as well. Methodologically, a dyadic approach relating self-reported and other-reported survey data of US-professionals was selected. Further, to represent career success in its entirety, especially in new work environments, four measures of objective career success as well as a multidimensional subjective career success scale were included. The interaction between narcissism and humility indicated negative effects on leadership position, project responsibility and salary. However, when the working environment is included, the humble narcissist is materially successful in the new world of work. In total these findings contribute to existing knowledge of both bright and dark personality by showing that psychopaths and especially narcissists can be quite successful in their professional life. Emotional stability and conscientiousness proved to be the relevant predictors in a professional setting. Supplementary to the important content-related insights, this thesis further contributes to an increasing body of research incorporating language and personality. It encompasses as one of the first studies that introduces elements of artificial intelligence to the research streams of personality and success by using an automated psycholinguistic analysis technology. This dissertation further contributes to the literature on paradoxes in the workplace by enhancing previous leadership approaches. While positive effects of paradoxical personalities have already been found at the top management level it was demonstrated that this phenomenon couldnt be converted to the general career success perspective. Further, by expending the research focus to new modes of working it could be shown that the working environment in todays organizations proves to be an essential contextual factor impacting an employees career.