Set my model up in a dark room with the camera on the tripod and strobed her with my Sunpak 383 (with black paper around it in a tube to focus the beam). Did a ton of takes, very few actually facing the camera, but I found this quite effective.
Debated about the desaturation but went with it because it lends a little more to a 'night' feel.
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Composition: Okay...I like the idea. And yes, insomnia generally takes place in the bedroom...but again, this image is cluttered. Try and keep the image with as little details as possible. Ask yourself......does this item or that item need to be there. Also, I feel those shelves really cut the image up....they enclose the story and the majority of the image into the bottom two thirds...and that can hurt the score.
Technical: I understand why you chose BW tonings...to make the viewer work out the story without the colours doing all the work. But you need to work on the tonings themself. A dramatic and draining scene such as this really needs heavy tones...to express the mood straight up to the viewer.
Overall: I feel you were on the right track...and you knew what you wanted, but you became frustrated at not being able to put it into one story. Keep trying and watch details. Ask yourself if that needs to be in the image and work it from there. Draw the image on paper and build it from there. You will find that half the clutter wouldn't have made it to the piece of paper...so why should it make it to the final photo. Good luck and keep experimenting.
Good use of multiple exposures and nice composition. Only thing I would suggest is that for the shot on the left to have kept the eyes open, since it would have conveyed insomnia better (looks like he's sleeping over there).
Clever idea. Like the multi-exposure idea (or multi-flash and using the bulb setting). I think color would have been better, and a harsher lighting angle. One of the better ones in this challenge