This 27-page research paper presents insights from a study focused on the experiences of individuals in leadership roles dealing with their chronic illnesses at work. Unlike acute illnesses, chronic conditions require ongoing management and can involve unpredictable flares, posing challenges to those dealing with them. The research highlights how these individuals grapple with disclosing such health issues due to social stigmas. Key findings include: 1) Disclosure Patterns: 28% chose non-disclosure, 54% shared partially with trusted colleagues, and only 18% were fully transparent. 2) Career Impact: Many leaders feared that revealing their chronic illnesses would lead to doubts about their abilities (42%), hinder promotions (39%), or stall career growth (38%). 3) Concealing Illness: 73% admitted to concealing or downplaying their illnesses by hiding symptoms during virtual meetings or providing alternate reasons for absences. 4) The Impact of Organizational Culture on Disclosure: A leader’s tendency to disclose their illness was significantly correlated with whether the company culture engendered feelings of psychological safety. This result implies that the very leaders responsible for creating a culture of psychological safety may be the ones who don’t feel it is safe to share information without it resulting in negative consequences. The report offers suggestions for fostering an environment that encourages disclosure and accommodations for those managing a chronic illness.