Words matter. They have tremendous power to heal or hurt. And although the patients we care for in oncology and palliative medicine often die from, or despite, their neoplastic illness; caregivers and loved ones often hold onto the words that clinicians share with them during their times of struggle and grief. In this narrative, the author (as first person) reflects on some systemic challenges he faced in dealing with illness and loss when his father battled two distinct neoplastic processes. He explores the commonalities and differences that he experienced as a palliative care physician, and how that has guided his medical practice moving forward. Moreover, he shares his observations regarding breaking bad news, code status discussions, and transitioning to hospice—as a cautionary tale to all clinical providers that what we say to patients and families matters. He encourages clinicians to avoid losing sight of the power and responsibility we all have to provide optimal, patient-centered care.