I've only been writing code for so long, while I grew up designing web-sites, it really doesn't count; so, as of now, I've been invested in programming for more than four years but have never had the courage or foresight to write something in OO. However, for the past couple weeks I've been pouring myself into the OO textbooks, yet I still don't feel reassured in it's value. So, as of today I can speak OO, since I know all the jargon, but I still can't muster up the courage to write an application that seems practical to me, which is where my problem lies. I'm also no software-engineer, but I've come to face the facts that my vision of building tools/programs/output is flat; so please, inspire me with your wisdom from 30,000 feet above, metaphors, philosophy, and expression by comparison is welcome.
EDIT: I guess the origin of my writers block in doing something in OO is that I don't really feel like I'm handling real data. I feel like I'm defining and declaring spaces as I see fit, thus leading me down the path of this pseudo/pretend file-system while ignoring the platform I'm really working on. Please prove me wrong.
Bonus analogy:
The web itself is object-oriented. You ask a server to return a resource for a given URL; what server it is (Apache; IIS) and how the content is generated (static page; CGI; PHP) is unnecessary for the conversation.