it's a hard leap.  i was classically trained and it took a while.  sometimes it just takes time.  do the 2-5-1 scale exercise in all keys over and over again, every day.  that really helped me.

then when you are learning a song, say on green  dolphin street (my first jazz song), don't be root bound.  try to hear the harmony in your head without playing the root of the chord, or try playing the root of the chord in the middle of the chord instead of below.  once you get away from building things onto the root of the chord, your playing loses some boundaries...

but it's not easy!  so keep it up and don't get discouraged.  at some point in time things will click and you'll be happy you stuck out all the hard work.

not to bow my own horn, but my book might be helpful (see the home page of this site).
If I'm not back in 24 hours, call the president.

Scot is available for skype jazz piano lessons (and google hangouts, phone call, etc...)
Use the contact link at the top of the page.
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Jazz Piano Notebook Series
Scot Ranney's Jazz Piano Notebook, Volume 1 - jazz piano tricks of the trade

Volume 1 of this educational jazz piano book contains 15 jazz piano exercises, tricks, and other interesting jazz piano techniques, voicings, grooves, and ideas Scot Ranney enjoys playing.

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Scot Ranney's Jazz Piano Notebook, Volume 2 - jazz piano tricks of the trade you can use today
"Latinesque"

Volume 2 has 14 jazz piano exercises and tricks of the trade, and quite a bit of it is Calypso jazz piano related material, including some Monty Alexander and Michel Camilo style grooves. Jazz piano education is through the ears, but books like this can help.

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Tim Richards' Jazz Piano Notebook - jazz piano tricks of the trade

Volume 3 contains 12 jazz piano exercises and explorations by the acclaimed jazz piano educator, pianist, author, and recording artist Tim Richards.

Tim wrote the well known "Exploring Jazz Piano" and "Improvising Blues Piano" books and has several others to his name.

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Jeff Brent's Jazz Piano Notebook - jazz piano tricks of the trade

Volume 4 is by Jeff Brent, a jazz pianist, composer, teacher, and author of "Modalogy" and other acclaimed jazz theory and education books. In this book Jeff shares detailed analysis of transcriptions of live performances. He covers everything from the shape of the songs to the tricks and licks he uses in improvised lines to the ideas behind his lush chord voicings.

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