This paper uses the personal histories of two men, born in the same decade and both involved in the field of adult education in Scotland, to illustrate contrasting responses to the social and political changes taking place in the early 20th century. In methodological terms, it draws on recent writing on the relationship between biography and history. Both men came from working class backgrounds, attended Glasgow University and considered becoming church ministers. But both retreated from a religious vocation, one retaining his faith, the other rejecting it completely and replacing it with political ideology. Their very different types of involvement in adult education are described and analysed, noting in particular their opposing views on the Workers' Educational Association. Possible reasons for their divergent pathways are explored in the final section. How much can be attributed to family background, individual psychology, networks of associates, attitudes to existing institutions, and a desire to promote greater social justice? How successful were their efforts to encourage community development (in one case) and class consciousness (in the other)? Why has one become a folk hero of the political left while the other, notwithstanding a strong public profile during his lifetime and a distinguished academic career which gained him international recognition, has been consigned to historical footnotes? While no definitive conclusions can be drawn, the analysis serves to illustrate the complex connections between personal biography and social history.