<human>: I have noticed that words can be used in incredibly interesting and sometimes counterintuitive ways to accurately describe very complex things very succinctly.  While I can do this sometimes I feel like I am known among my friends for saying way more than anybody else and taking many more words than they do to make my point.  I also notice that I have trouble vocalizing concepts in my head when other people can do it with ease. 
What sort of things should I try and are there any techniques or tricks to organizing and/or describing one's thoughts?

My goal (maybe unrealistic) is to have the ability to debate as well as Jon Stewart.

Condense the text into a few key points
<bot>: You can only use words like insular and hifalutin so many times before people notice they're the only big words you know. Help.