Had I won the September Challenge, I was going to suggest that we design an Enterprise Era (mid 22nd Century) commercial or personal site of some kind.
Years ago, the Internet didn't exist. Information was written and transferred via letter and courier, telegraph and telegram, facsimile, and eventually by old one or two line bulletin board systems. When the Internet did emerge, it was primarily text based. Gopher Sites fed information while FTP sites were where you'd find all types of binaries (pictures, midi files, etc). Later, the paradigm shifted and Web Sites emerged with "rich" content blended with images. The so-called "Web 2.0" elevated Web Sites' level of interactivity with the introduction of AJAX and the proliferation of API based modules (think of Youtube on this BBS, or Facebook applications).
Each of these paradigm shifts changed the way we interact with information, and with each other. Today we write our memoirs, connect with far flung relatives and friends, play games, engage in commerce, and so much more.
My challenge would have been to think about not only what's coming next, but what's coming after that -- to imagine a paradigm shift in information storage, interactivity, and dissemination. But beyond the art, how will it effect/enhance/change the lives of our great-great-great-great-great grandchildren?