In 1964, Marshall McLuhan identified a new phenomenon in modern society. That year, McLuhan published Understanding Media, a book of essays focused on the pervasive effects of new media on our lives. McLuhan predicted that the microchip would change the way we conduct business, communicate, entertain and learn. He condensed the world-shaking prophecies into the saying “The medium is the message.” We are just beginning to understand the implications of his words. This phrase referred to the fact that media (as extensions of the human mind and body) are inextricable from but independent of their content (human thought). Although these words are esoteric, they have shaped my study and practice of educational technology at San Diego State University. As my studies progressed and my skills developed, I realized that the idea that “the medium is the message” is essential to instructional design. . The ever-changing media that instructional technologists must embrace require that we understand the full range of potential cognitive benefits and pitfalls associated with each medium. We must now take a close look at the "possibilities" (or unique and beneficial properties of a medium) and constraints (or limitations) inherent in each new technology we use. This secondary reading of McLuhan's expression leads me to a design process that I call "Conversion." Conversion, as a design metaphor, describes the movement of content through media in a way that takes advantage of a new medium's possibilities and overcomes its constraints. It is a philosophy that requires an in-depth study of how individual mediums work and how we can use media to achieve our goals. The conversion is also grounded in contemporary cognitive science research,...... middle of paper.... ..the process of converting an existing design into theoretical structure helped me understand the power of accidental learning. Finally, the look and feel of the portfolio is the result of the conversion. When I started, I tried to create the portfolio from scratch using a standard website layout. Technical issues and compatibility issues have plagued the page. At this point, I tried to co-opt a WordPress.com blog to add a more efficient structure to the site. I started using the possibilities of blogging (a clear hierarchy and structure, dozens of predefined layouts and customizable interfaces) to improve my portfolio. This conversion from a blog to a portfolio solved not only my technological problems, but also a number of design problems. These projects chronicle the transformations that occurred in my design process even as I guessed, played, and discovered my way through the master's program..