This article introduces a simple mapping tool called Grassroots, a software product from a longitudinal study examining the use of information communication technologies and knowledge work in communities. Grassroots is an asset-based mapping tool made possible by the Web 2.0 movement, a movement which allows for the creation of more adaptable interfaces by making data and underlying database structures more openly available via syndication and open source software. This article forwards three arguments. First is an argument about the nature of the knowledge work of everyday life, or an argument about the complex technological and rhetorical tasks necessary to solve commonplace problems through writing. Second is an argument about specific technologies and genres of community-based knowledge work, about why making maps is such an essential genre, and about why making asset maps is potentially transformative. Third is an argument about the making of Grassroots itself; a statement about how we should best express, test, and verify our theories about writing and knowledge work.