I've been playing guitar on and off since I was in my early teens. I played mostly folk and rock, plus a little bit of blues. I started performing as soon as I could play a few songs.
I grew up around classical musicians and do have an appreciation for some classical music. Never studied, though... my guitar skills were "self-taught".
I've always preferred music that had some good harmonic ideas: prog-rock rather than blues, folk rather than metal, Beatles rather than Rolling Stones, etc.
Somehow, I never warmed up to jazz...
Five years ago, near my 45th birthday, I started getting interested in music again. Even though I'd barely touched a guitar in the prior twenty years, my playing skills came back quickly. I formed the first of several bands, co-wrote some original rock-ish material, and started playing out. I quickly grew frustrated; not with my performance ability, but rather with my ability to communicate with other musicians and my ability to create "interesting" material.
At that point, I realized that I needed to dig deeper. I started learning about music theory, and sought musical "bridges" to help me understand jazz starting from the kinds of music I already understood. This group has been a very useful source of both information and inspiration. Fewer conversations go completely over my head now than a couple of years ago.
I've developed a better understanding of the intervallic relationships on the fretboard. I understand how chords are constructed and can even puzzle out the spelling of a chord from its fingering. I've thrown away my "chord calculator" programs. I've even started to develop an appreciation for the uses of different chord voicings, particularly with respect to moving from one chord to the next. Kind of a pre-cognitive understanding of voice-leading, perhaps... ;)
Meanwhile, I've grown weary of rock bands and quit my last band in August. I do miss performing, but not the countless hours of unproductive rehearsals, the "point and grunt" approach to communicating musical ideas, and the lack of subtlety and finesse in the music itself.
I've thrown myself into study and practice and am enjoying new discoveries and challenges. After a few months of working on lots of different areas with no particular plan, I've decided to commit to studying a "method". I'm most likely going to go with Jody Fisher's jazz guitar series, since it's explicitly targeted to players who, like me, are arriving at jazz from a rock background.