Self Portrait headshot critique

Other than the ugly dude in the photo, what would you guys have done differently? This was quite a challenge for me. I am somewhat new to off camera flash, and really struggled with the black background. I first tried this indoors but with my relatively small room size and only a shoot through umbrella for a modifier, I was getting a ton of spill no matter what settings I used and I couldn't get far enough away from the walls to get them black.

So I took it to the yard after dark. It was pretty hard getting the shot framed how I wanted it, as well as getting the light how I envisioned it. This is fairly close to what I had in mind, so I went with it. Would a hair light have helped? I know my hair blends in with the background, but I am not sure I mind it that much.

Any comment or critique would be very much appreciated. Not only on the photo itself, but also on the struggles mentioned above. Thanks in advance.

IMAGE LINK: http://www.flickr.com/​photos/bmax-photo/8739068015/

Backlight. The hair is lost.

Qbx wrote in post #15933408
Backlight. The hair is lost.

Yep - That's the first thing you notice.

Personally cropped too tight at the top. The hair needs backlighting as already mentioned and I would change the pose turning the head to either fully show the right ear or exclude it altogether. Small points and otherwise a great shot with good lighting.

John.