Well, on what've your recent searches been focused, and how've you felt about whatever it is you've been hearing? Answer those questions, and you'll have a better sense of where, exactly, you are...and, more importantly, where you think you should go, next.
And, yes--I completely understand your struggle. I have recently tried to tie things down generically (ie, in terms of genre), when going through recordings of the past. This can be limiting, to an extent (and problematic, in an abstract or theoretical or even cultural sense), but as long as you're not too prescriptive or restrictive, I think it can work quite well. I have tried to FULLY explore one/two areas, per year.
Last year, I tried to learn as much about Reggae music as possible--I bought books, downloaded dozens of ancient albums, bought dozens more, and just had a grand old time. From Reggae, my searches took me into the rest of the Caribbean, and I found myself particularly taken with Calypso and steel drum music (as well as lots of proto- and post-Reggae). It was a great year for discoveries, and my model served me well.
This year, as I have been mentioning, I'm trying to put myself in better touch with the garage and psych movements of the late '60s and early '70s. I have also found myself being drawn into regional, "English" folk (Meic Stevens, Fairport Convention, etc.) and lots of newer, under-the-psych-umbrella stuff (Brian Jonestown Massacre, Boris, Beachwood Sparks), as a result. My listening has been more hit-and-miss than last year's weed-a-thon, but it has still been an awesome experience. The internet is such a powerful tool, and allows me to make such better decisions about what to ignore and on what to focus my time, energy, and money.
Make the most of your time, and don't be afraid to hook up with other, more diverse boards. There is a whole wealth of information and experience, out there, just waiting for you to soak it all up!
And, for what it's worth, I couldn't recommend strongly enough the psych stuff about which I've been posting. Holy shit, it's been a while since I've had this much fun with old records (or new records inspired by them!). The first Shadows of Knight LP, Gloria, fucking kills!