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Individualizing the goals of care discussion is challenging, especially at the end of life. This article explores some difficulties with goals of care planning using a clinical scenario involving a decisionally impaired elderly African–American female with advanced chronic lymphocytic leukemia and dementia facing a life-threatening condition. Physicians should personalize divergent goals such as a cure, rehabilitation, life-prolonging care and comfort care after factoring in individual patient preferences and disease trajectories. This case illustrates the barriers to the goals of care discussion: lack of education about the disease progression, poor communication techniques, poor language choice, not having proper decision-makers present and lack of trust between the decision-maker and the healthcare team. Harnessing technology can cause breakthroughs in the future.