Those working in the fields of harm reduction, healthcare, and human services must cope with a range of stresses, including post traumatic stress and vicarious trauma. Pain and loss are just a part of the job. So is dealing with premature death as a result of HIV, hypertension, and even overdose. Faced with a range of challenges, some workers in the field even turn to self-medication. For some, it is about pleasure; for others it is about alleviating suffering. In recent years, several leaders in the AIDS and harm reduction fields have died ahead of their time. Some stopped taking their medications; others overdosed. Rather than weakness or pathology, French sociologist Emile Durkheim saw self-destructive behavior as a byproduct of social disorganization and isolation, as a way of contending with a breakdown of social bonds and alienation. There are any number of reasons why such behavior becomes part of work for those involved with battling the dueling epidemics of Hepatitis C, HIV, and related concerns. Forms of stress related to this work include secondary trauma, compassion fatigue, organizational conflict, burnout, complications of direct services, and lack of funding. Faced with day-to- day struggles over poverty, punitive welfare systems, drug use, the war on drugs, high risk behavior, structural violence, and illness, many in the field are left to wonder how to strive for wellness when taking on so much pain. For some, self-injury and self-medication are ways of responding. Building on ethnographic methods, this reflective analysis considers the stories of those who have suffered, as well as a few of the ways those in the field cope with harm and pain. The work considers the moral questions we face when we see our friends and colleagues suffer. It asks how we as practitioners strive to create a culture of wellness and support in the fields of harm reduction, healthcare, and human services. Through a brief review of losses and literature thereof, the essay considers models of harm reduction practice that emphasize health, pleasure and sustainability for practitioners.