Based on 31 interviews with workers (ten nurses, six social workers, seven music therapists, three integrative therapists, one chaplain, one certified nursing assistant, and three bereavement counselors) from a large, non-profit hospice organization in the southeastern U.S., this dissertation examines the challenges that arise in hospice work. Hospice’s provision of end-of-life care is becoming even more important as our population lives longer. My analysis reveals some of the challenges that hospice workers face in a continuously changing health care system. First, conflicts may arise between workers and their clients. One source of conflict between workers and their clients is that the subject of death is considered taboo in U.S. culture. This causes patients and families to be in denial of the impending death, to be uninformed about and therefore unprepared for the processes of dying and grieving, and to push for curative treatments, which is antithetical to hospice philosophy. My participants attempt to cope with these challenges by educating their clients. A second source of conflict between workers and their clients is that the public incorrectly believes that hospice is a place one goes to die. This causes patients and families to enroll in hospice too late, to be suspicious of or even reject palliative medications such as morphine, and to request euthanasia, which is antithetical to this hospice’s policies as well as against the law. My participants attempt to cope with these challenges by educating their clients, acquiescing to their clients, or looking the other way. A third source of conflict between workers and their clients is when differences arise due to culture, religion, or the unpredictability of a patient’s mental condition. My participants attempt to cope with these challenges by setting aside their own opinions and serving their clients with as little judgment as possible. My analysis also reveals that workers face many challenges due to hospice becoming more like a business. This hospice organization’s attempts to expand its client base has resulted in my participants experiencing quantitative as well as qualitative role overload and adjusting to work in different settings. My participants attempt to cope with these challenges by sacrificing time with clients, abandoning professional socialization activities, and engaging in impression management. This hospice organization’s division of labor has resulted in my participants feeling alienated from the hospice process, experiencing role overlap in the Interdisciplinary Team, and being frustrated with the irrational consequences for their clients. My participants attempt to cope with these challenges by communicating openly with their clients and with each other as well as setting aside their own feelings and opinions. Finally, this hospice organization’s focus on cost containment has resulted in threatening the worker-client relationship as well as increasing workers’ load with the need for more documentation. Workers also point to the blurry line between care versus cure and complain of the prioritization of “medical” over “non-medical” care. My participants attempt to cope with these challenges by accepting their work conditions begrudgingly, decoupling themselves and their work from management, educating their clients as well as each other, using clients’ lack of knowledge to their advantage, and setting aside their own feelings and opinions. My analysis contributes to the exploration of stressors in paid work in general and in hospice in particular.