Federal Government Contracting => Startup/Commercial Freelancing (US Government couldn't care less about spending tax dollars well...)

Living next door to the 'rents (for help with wife's health care) => Living 150 miles away

Java => Ruby (and almost any language, including JVM languages, other than Java)

PC => Mac (huge +1)

Friends who don't respect my life choices => Friends met through the Ruby community

HDD => SSD