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The purpose of this phenomenological study is to discover the impact of high-achieving executive leaders who neglect their trauma and insecurities on business decisions and success outcomes. For the utility of the study, trauma was defined as the chronic altering of emotional or cognitive processing of the brain due to an adverse experience. Insecurity was also defined as a negative perception of oneself due to a lack of certainty in safety, worth or capability. The selfdetermination theory and the implicit leadership theory informed the theoretical point of view guiding this research. A qualitative method with phenomenological research design was used to answer the research question: How has success for high-achieving executive leaders become a perceivably evolving, unattainable goal driven by trauma and insecurity that affects business decisions and outcomes? The study setting included existing data from an academic researcher and does not have a specific geographic location limitation. The study sample included thirteen primary interview participants of varying industries, ethnicities, genders, and backgrounds who obtained objective career success and were considered high performers. Data collection methods were interviews which were facilitated through the virtual meeting platform Zoom. Procedures included the researcher coordinating interview dates and times with individuals who expressed interest in participating in the study. Zoom platform information, a consent form, and a message verifying the sending of the consent form, including interview questions for the interview were sent ahead of time. Study results identified themes of Childhood Parental Dynamics, Social Proof, Coping Mechanisms, Work Ethic, and Quality of Life as contributors in the experiences and outcomes of high-achieving executives.