I am BEYOND excited to finally comment on this (with my coffee in hand!). I read it when you first posted it and audibly muttered "What!". The title is unique, and I feel like you've done this before, where you take two words that usually wouldn't be seen together (or two ideas), and mold them together. The way you personified this shadow from start to finish made this poem stand out even more, and I just love how, from the title, I knew this would be like nothing I'd read before.
What I took away from this is that even in our tears, there is still something that awakens inside of us. Maybe a desire to escape, to have a taste of what it's like to travel and get away from everything we know. Or maybe the open seas and fluffy clouds signified eternal rest, or this "fantasy" land, where there is no more bad in the world. I took the caffeinated part as both literal, and as having a spirit that is yearning for more adventure, pulling at us even when we simply want to rest.
My favorite lines:
"this time he approached
the deaf side of the night,
the side where I wept,"
^ The most poetic lines in my opinion! I also liked that, a few stanzas below, "but no one listened" was on its own separate line.