Portrait Challenge

I've given myself a challenge that has me make an attempt at 100 portraits.  I'm working on portrait number three today.  There is a long journey a head of me right now.  The first 50 of them are going to be in Photoshop.  I'm going to try and make the first 25 of them monochromatic and then go into color from 26 to 50.  From there I'm going to move on to traditional media.  From my point of view right now this looks like it's going to be really hard.  Digital painting has been such a mystery to me, so with 50 portraits underway I hope that I have a really good grasp on it in the future.  I'll try and post five portraits at a time.