how do u play this way? i can play solo piano, but how do u accompany yourself while u sing?
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i came from the blues initially, and i think what helped me was that certain blues passages repeat themselves.  another thing that helps is to live with the song long enough that you don't worry about the changes (you already know those right?) you just sing along.
break it down like you would left hand and right hand, except in this case think of it as left, right, voice.  do only one or two measures at a time, slowly, until you can coordinate all three for an entire passage.  also, have the piano part learned thoroughly in advance, as it will make it much easier to add your voice.

also, try learning the piano part so well that you can play it with your eyes closed, and then sing over it with your eyes still closed.  i don't know why it works, but i've learned to sing/coordinate some difficult songs that way.
oh...and as far as learning what to play, listen to some of the greats: nat king cole, diana krall, shirley horn, dr. john, freddie cole, mose allison, katie webster, and even oscar peterson (on his "with respect to nat" album), just to name a few.
music is essentially a juggling trick.

singing while playing is just one more ball in the air.

you'll want to play more rhythmically and sparser whether you are accompanying yourself or others.

if you find that your singing is being hampered by some complex rhythmic figure on the keys, make what you're doing on the keyboard simpler.

while comping, it's perfectly ok to throw in fills whenever the singer takes a breath, in fact it's more or less expected.

if necessary go all the way back to square one if you have difficulties and rebuild it from there.

consider that in many bands you will not only have to play the keys and sing, but you'll also have to do dance steps.

once you've practiced enough, it will become second nature. but it can definitely take awhile and there is no magic bullet. the quality of your singing is paramount. if you are not satisfied with the way you are singing, sometimes you will find yourself obliged to work on just one single syllable before you can insert it back into the song.

it has been my experience that the human voice is the most demanding (yet most expressive) of all instruments. you can spend a good part of a lifetime to get to the point of being able to sing not only properly but with great effect and emotion.

take your time and do not become discouraged. rome was not built in a day.
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