Studies establish that cybersecurity executives face complex difficulties from constantly shifting risks due to the role's scalability and increasing responsibilities in this cyber-revolution. Cognitive and emotional aspects can influence change and decision-making, especially during times of heightened anxiety and evolving change. Through qualitative study and interpretative phenomenological analysis design, this research offers how leaders' 16-hour or more per-day working schedules affect the companies' readiness, how working hours affect leaders' resilience, and whether leadership traits like longevity, tenure, and other similar characteristics should be considered when estimating cyber risk insurance. This study aims to strengthen the defense-in-depth perimeter by providing a means to proactively identify factors that align with an enhanced approach to better estimate appropriate cyber liability coverage. Beneficiaries of this research are cybersecurity leaders and practitioners, academia, organizations that employ cybersecurity, and cyber risk insurance brokerages.