A work in progress

This portrait is a work in progress, getting there, but still not quite what I want. I'm a friend of her mom who, knowing I love to fool around with portraits, asked me if I'd like to try shooting a portrait she can use for web publications. I leapt at the chance and told them it will cost them a scoop of ice cream, and we had our first shoot today, but I'm not satisfied with the result. We're having a do-over in a few days, and I thought I'd post this to see if anybody has any helpful ideas for me.

I want professional but edgy, kind but not a push-over, smart but not severe, soft but not mushy. She's Alyssa Siegel, a therapist, a second-generation sex therapist who has collaborated with her father on a book called Your Brain on Sex. In a brief article on "Punk Parenting," she describes her client-base as "activists, radicals, and creatives." I want a portrait of her that says to that group that she's one of them, but she's also capable of helping them out of whatever rut they might be stuck in. You can tell she's brave; she let me blip this and put the query out to my Blip community for suggestions.

This shot is getting there, but it's not the one. We shot this in the vestibule of her apartment building because we both liked the light there, but maybe the white pillar was too harsh--the contrasts seem thin to me, and I don't have the kind of clarity I usually go for. Depending on what the weather is on Thursday, we could do the new shoot inside, outside, or in-between. We'll need available light because I don't have any fancy equipment. We took some shots showing the tattoos, some not showing them; some more or less radical jewelry, with and without background. Ideas? Suggestions?