My avatar originated in 2010, while I was working as a designer at Opower. Each person on the design team illustrated a self-portrait that we would use to create a combined team portrait. In the original version, I was holding a opossum playing dead. The opossum was sort of an unofficial mascot that we'd made up, and well, I'm originally from West Virginia.
The avatar has seen a few revisions over time, and the current version is almost completely hand-coded and hosted on GitHub.
Over the years, I've made a few variations for special occassions.