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This thesis examines the nature of an electronic medium known as hypertext in relation to the act and experience of writing and expression. Essential to the thesis is a conviction that the experiential realm that is created by a particular medium of communication and/or representation is capable of also creating new 'habits of mind' or 'worldings.' These two concepts are indicative of the intensity of experience that is made available via an expressive act and the extent to which the various aspects of this intensity are capable of transformations on personal and public levels. / One of the central issues of the thesis is an ongoing re-evaluation of the euphoric claims that trumpet hypertext as usurping the so-called tyranny of the book and the domain of linear thinking in general. In many evaluations of the medium, hypertext is commonly presented as a communications medium that offers a far greater panorama of choices and freedoms than does the printed word and, in addition, is far closer to the way in which the human mind 'actually works.' One of the intentions of this project is to not only critique and study such claims but also to explore their numerous offshoots with respect to cultural, philosophical and ideological practices and techniques. Thus, this thesis unfolds via four major thematic clusters that each, in its own way, challenges and probes at the emerging medium of hypertext as it relates to the activity and cultural practice of writing itself. / The first of these clusters is organized around the challenges and problems of constructing an appropriate interpretive methodology with which to approach hypertext. The second cluster offers an analysis of hypertext's defining characteristics and their relation to melancholy, isolation and anxiety. What follows is an analysis of the major figures in the history of hypertext and their relationship to the dynamics of power and knowledge. The thesis concludes with a meditation on how the act of writing (electronic or otherwise) has profound implications on the very structure and form of the creative human mind and world.