in reply to The Road to Enlightenment?
The usual playing around, then using it when I could at work, etc.
My biggest jump in enlightenment came when I read the first few chapters of Conway's Object Oriented Perl. It covers, among other things, closures and the OOP stuff. Computer Science & Perl Programming: Best of TPJ is also good stuff.
Since then, using Perl to apply things I've learned during my education have helped keep things fresh.