Authors and other creative workers today are faced with the (r)evolution of digital technology and media that slowly change and challenge the way they create, disseminate, and preserve their work. The purpose of this paper is to explore the attitudes, habits, and practices of contemporary Croatian writers in a small-scale sample in terms of the creation, organization, and preservation of digital documents and various literary forms. Data was collected through semi-structured interviews with nine contemporary Croatian writers and examined through narrative analysis of the interview transcripts. The research highlighted areas that need to be more thoroughly considered when we are dealing with issues of personal digital archiving, digital legacies, and the preservation of digital cultural heritage in general. In-depth interviews with respondents indicated one particularly important issue: that preserving the context of their work is as important as preserving the work itself.