An Update: Change is always a part of music and yourself
My first year of graduate school is finished and it's been everything I needed and wanted. I'm lucky to be studying with an honest faculty here at Michigan State University Jazz Studies department.
Changing the way I understand improvisation has been a huge turning point in my thought process, my musicianship, and improvisation approach as a jazz musician. This is a crucial process that I have found be tedious and humbling. Doing the work that requires us to learn from the jazz masters isn't hard to figure out or to do. What's hard to figure out is how to implement what we learn form the jazz masters and make it become a part of our playing. We have a preemptive thought of what we want to sound like already and breaking from that for the good of the music is one of the hardest parts of the process of learning jazz language. For myself I had many tendencies that are still being worked out of my playing and are progressively changing in order to keep the music true and with intent.
Implementing jazz vocabulary is difficult when you're first starting out. I find that repetition of using the same piece of vocabulary you're working on is what gets you the fastest results. Using the piece of vocabulary you're working on using different standards than the one you learned it from is also crucial because it teaches and reinforces how to implement that piece of vocabulary into your playing without limiting you to one tune or one sort of progression. This goes hand in hand with learning them in all 12 keys. For example; the bridge of Cherokee is ii-V's in whole steps and when you have multiple lines of vocabulary in 12 keys this sort of tune gets somewhat easier depending on the speed you play the tune at.
Where do you learn the lines? You learn them from transcriptions of the masters/pioneers and practice them like crazy until you get that sound and line in your head and at your disposal. Now time for me to go do more of this! See some of you around if I'm in your part of the country this summer. I'll be in NYC May 14-18th. Lets hang!