Helping others with significant issues in their lives can be highly effective, satisfying, and meaningful. It can be great work. But to do this well, we must constantly attach and separate successfully, over and over again, with person after person. It can be difficult work. What is the nature of this difficult work? In this paper, we reviewed the difficult nature of the work in the high touch people fields---sometimes called the helping professions, the caring professions, or education, human services, and health occupations. The difficult nature often has to do with characteristics of clients, students, and patients we desire to help: they have an unsolvable problem that must be solved; they are not honors students; they have motivational conflicts; there is a readiness gap between them and us; they sometimes project negative feelings onto us; we cannot help sometimes because we are not good enough; and they have needs greater than the social service, health, or educational system can meet. The difficult nature of the work also has to do with major professional stressors of caring professions: our inability to say no, living in an ocean of stress emotions, ambiguous professional loss, the covert nature of the work, constant interpersonal sensitivity and one-way caring, transference-countertransference data, elusive measures of success, normative failure, regulation oversight and control by external others, legal and ethical fears, vicarious traumatization, and primary trauma. With all these stressful qualities of the work, we must continually invest positively in others. How can we do it? It is the goal of portraying the difficult nature of the work in this paper to invite those in the caring professions to balance other-care and self-care on an ongoing basis.