This essay presents a model of reflective use of writing technologies, one that provides a means of more fully exploiting the possibilities of these tools for transforming writing activity. Derived from the work of computer designer Douglas Engelbart, the "bootstrapping" model of reflective use extends current arguments in the field regarding the role of technical expertise in writing. Individually, and as a discipline, we can use Engelbart's example as inspiration for assembling unique systems of tools that extend our sense of what is possible in terms of producing and distributing texts. (Contains 6 notes.)