How many times have you heard somebody say that they were never able to get into jazz because "I don't understand it?" Maybe you are that person? Well, I want to let you in on a little secret — There is no right answer.
Yes, you read that right. It's very much like those daunting questions in high school literature class..."In this story, the mountains are symbolic of what?" Technically, there is a correct answer, but that doesn't preclude the reader from from enjoying the writing. Related to this secret is that the listener is allowed to bring their own point of view to the process. The actual technical content of the music is not nearly as important as how it makes the ears feel.
Let's take Jacky Terrasson's solo version of "Caravan" as an example of how my jazz brain works. What follows are the notes scribbled down after the first few listening passes:
"Spinning & shifting figures lead not into chaos...but the opening vamp"
"Caravan, the straight version, is there...but it's implied"
"Tarrasson drops in shockingly loud chord accents"
"...deconstructs (no...melts) harmonic structures"
"Cool quote from Well You Needn't"
"Reveries are born of the moment, though even the 'out' ones make perfect sense"
Sure, there's some music-wonky language in there, but that shouldn't mean anything to you. Just allow your analytical self to relax and focus on what parts of the music make you feel good (or not!). Don't concern yourself with the 'why' because, honestly, it doesn't really matter.
I'll leave the rest of Terrassons's Mirror as an exercise for the listener. In many ways, Terrasson's approach to the music, especially on standards, provides the perfect environment for discovery. Some musicians approach a collection of tunes from a particular angle. Terrasson does this within the components of each composition.