After realizing my mistakes I immediately called Buddie up and requested for a re shot. He has the look I was looking for, I just had to capture it. I also emphasised that it was critical for him to shave, and to have his shirt pressed. The next day Buddie came in and we got the shot I was looking for. I adjusted the lights to fill in the shadows by his eyes and also added a little blur to soften his face. In the end we got. Thanks Paul for all the help.