Jonathan Coulton is a singer/songwriter dubbed the Godfather of Geek Rock. Contrary to what that title may imply, he's actually really fucking funny.
If you take the ironic, absurdist tone of Dr. McNinja, mix that in with influences in classic and soft rock, and add the experimentation and facial hair of an indie band minus the pretentiousness, you get something a bit like Jonathan Coulton. A former code monkey (making his song Code Monkey at least somewhat autobiographical one suspects), Jonathan quit his job, started Thing a Week as described above, and managed to build up a large, devoted fanbase that has actually allowed him to make a better living as a musician than as a programmer. The fact that this plan actually worked is in itself pretty mind-boggling. Seriously, try quitting your job to pursue an artistic career based on a blog. Go ahead, we'll wait.
Jonathan hit the geek lottery in this decision. Not only did he succeed in holding up Thing a Week for a whole year, he became a contributor to Popular Science magazine, performed for John Hodgman's stand-up and book tours, and was commissioned by Valve to write a song for the game Portal, which has become a flagship tune for all echelons of nerdom.
What have you done today?