The paper discusses the possibilities and limitations of vocational guidance in the social volunteering system. The essence of volunteer work is closely related with assistance to desperate people in searching for the meaning of living, often coinciding with labour activity that are deemed in terms of “the main matter of life” and “the leading activity”. For adolescents, it is the choice of career, and for adults, it is the work proper (i.e. an essential condition for personal self-realization). The problem of “forced volunteering” for experts in vocational guidance also means that they often have to work voluntarily and unselfishly outside the official guidelines. To clarify the terms «volunteer» and «a person in desperate need of help» the study used the method of analyzing the documents, e.g. the Regulations on Social Volunteering, the generalization of psychological sources, the initial survey of university students as active supporters of the volunteer movement, On the essence of volunteering and the place of career guidance in selfless social work. Vocational guidance is not excluded from the general system of volunteerism, but has an insufficiently defined status and low popularity among participants in social volunteering. Also, the problem of «forced volunteering» of experts in career counseling, which often requires voluntary and unselfish performance of quality work outside the framework of official instructions, is also indicated. Simultaneously, positive aspects of such disinterested career initiatives are noted, in particular, less control by the official inspectors (or customers) and, accordingly, greater freedom of creativity than when someone else does the work.