I've had the source image below for over a year. This month has been the first time I've attempted to sketch a likeness of it in pencil. My reason for not doing so before now....was a lack of confidence in my ability because it looked too hard (so many darks to be able to distinguish)..
That said, my first try began with a line to show the edge of the face on the right from forehead all the way around the chin. The effort below was done over several days. Even though it is 'finished', the hat could benefit from much more work in order to be a strong likeness. But overall I'm satisfied with the sketch where it is now. There is a difference that can be seen in my piece compared to the photo. The face in the photo is shorter [vertically] than mine. But it's not enough to make me want to re-do it.
The challenging areas were the eyes followed by the hat. What I learned is that I'm seeing shapes better as well as in more detail which adds to a piece's realism.
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