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Perhaps part of the "loosening up" that you're working toward could be realized in terms of thinking about simplifying shapes and values. I'll just refer to one area to try to explain what I mean, and that's the shadow side of the face. If you squint down enough as you look at the reference photograph, you can almost get to a point where it appears that you could represent the head using only two values, a very light gray and a very dark gray. It's not quite that clear cut, though, because there's a fair amount of reflected light, too, on the viewer's left, but let's get the big shape in first and deal with the reflected light as an adjustment to it. As you squint, you can see not only that the shadow side is very much darker than the lit side, but the contour of the shadow is quite sharply delineated. There's a virtual line, peculiar to this person's likeness, working down from hairline to Adam's apple, very distinctively describing the facial features, and on one side of that line is a very definite light and the other side a very definite dark.
As you squint at your drawing, you see instead a much more gradual transition between values and a very much more limited extension of those values. You've given up a lot of the benefit of that great lighting set-up. Within the shadow shape are lots of small patches of value that don't, it seems to me, do as much to suggest form as would an overall simplification of that whole large shadow shape. Keep as much unity in the value shapes as possible. Don't "look into" the dark areas too hard in order to be able to "see" subtle lights -- if the lights aren't there when you squint, then for the benefit of simplification, of "looseness", they aren't there, period. This includes, for example, all that light you've introduced around the eye on our left, an eye which in fact is in quite dark shadow.
By the way, the "rule" -- yes, the "should" -- on squinting is that it's used to simplify and discern the relationship between value shapes, but you don't want to draw the darks as dark as you see them when you're squinting.
So, make sure the contour of that shadow shape is carved out all the way down and around the peculiar angles of the Adam's apple. And note that the lit side of the neck is nearly as light as the lit side of the face, yet you've got it considerable darker. The two areas are actually part of the same unified light shape, only "accidentally" interrupted by the shadow on the underside of the index finger.
It's because the overall shadow shape is too light that you've found yourself overdarkening the lines of flesh creases on the neck and the small shadow are just above the collar. Squint at the hand as well, and you'll see there, too, that there really is not a dark black line separating the heel of the hand from the wrist, nor is that triangle of reflected light that bright.
The dark side of the shirt does need to have some lights pulled out of it (with a kneaded eraser), not because I'm "looking into" that area for light, but because there's such great constrast between the sides of the shirt that they look like two different garments. At least some small bit of light is crossing over to the shadow side.
One last item that may seem to go to fussiness rather than simplicity -- but doesn't really, since even simple gestures have to be correctly placed -- is the line of the mouth. That's very characteristic of this man's likeness, and I think the side of the mouth on our right has been represented as too narrow, and that it has remained horizontal too long before dropping down into that distinctive triangular shadow shape at the corner of the mouth. There's also a convex area on the contour of the cheek near that corner that I don't see in the photograph. Finally, squint at the left side of the mouth and that light running all the way across the top lip to the corner will disappear, as it should.
Security is sending a detail up to drag me out of here, so that's it for now. Squint. Simplify well-defined and correctly valued shapes. That will "loosen you up".
Steven
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