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the first part seems to be an invitation/opportunity for you to enter into a
mentor relationship where you might guide someone through difficult times,
due to your ability to see through their perspective and not be adversely
affected by 'frightful' scenes. your purpose in that endeavor would be to
bring clarity and peace to whomever it was you were assisting. this specific
shadow creature likely has no meaning, if you've not got someone in need
of help at this time.
part two seems unrelated. that you were flying (in a plane i assume), but
could view this activity from above that perspective is saying that you're
reviewing, or overseeing some aspects of your life experiences from a
higher plane of being (from the vantage point of your 'oversoul' perhaps).
the idea that you lose your shoes in the city makes me think that you've
got a non sophisticated viewpoint on the city life, as if you were a hick
or country boy... the hiking shoes are also somewhat out of place there.
that doesn't really hinder your performance in the urban setting, but it
provides you with a particular point of view for things. perhaps it's common
for you to forego a sophisticated understanding of things, in favor of an
unrefined attitude, which might account for your having forgotten about
meeting the rapper at an earlier time.
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