One afternoon in the third week of September 1994, I started writing myself a small Emacs extension using Lisp Advice to make Emacs speak to me so I could use a Linux laptop. As Emacspeak turns twenty, this article is both a quick look back over the twenty years of lessons learned, as well as a glimpse into what might be possible as we evolve to a world of connected, ubiquitous computing. This article draws on Learning To Program In 10 Years by Peter Norvig for some of its inspiration.