After doing an online course on headshots, I convinced the wife to stand in front of the camera and experiment with some different types of lighting. My first attempt was quite unsuccessful. I tried lighting her with a single ring flash with two speedlights creating a blown out background.
I think my second attempt was much more successful. I opened up two umbrellas and used clam shell lighting to take the following shots, underexposing the bottom "shell" by about 2/3 of a stop. I also had a third bare speedlight on the background. Each picture was shot with the 60mm macro Canon lens at 125th and f2.8. I concentrated on focusing on the front eye for each shot.