Jessie - Photography Assistant

I have learned from previous experience that the recipe for a difficult day of photographing jewelry is to be under prepared.  So this time I had all of my pieces ready (duh, I know, but sometimes things happen), I prepared a spreadsheet to organize what to photograph as well as how to photograph it and I had the background and display all set.  My charming photographer was patient and determined to have a finished product that I liked.  Despite almost dropping the camera and spilling about 1 lb of river stones onto the wood floor (which I am still finding in odd places), it was our most productive and congenial photo session to date.

Things had gone so well that the next day we went to the studio to attempt a new head shot since my current one is a couple of years old.  This is never easy, regardless of the amount of planning I put into it, and ended without a new photograph.

I need some suggestions...how do you capture a photograph that conveys who you are, has an artist edge and  expresses more personality than perfection?