1.) I think a tighter crop would help, there is too much dead space above his head. I would probably crop through the hat and get his eyes in the middle top 1/3 of the photo.
2.) The telephone poles and wires are distracting. You shot this at f/8, I would go to a lower power setting on your 1600 (if possible) and open your aperture up to get a shallower depth of field.
3. The skin looks funny and has hot spots. It looks like you did some kind of skin smoothing. What size and how far away was your softbox? You need to get that softbox in nice and close to get the softness and quality of light it is intended to produce.
4.) This photo might look better processed as an old time black and white with the proper crop.
Just my 2 cents.