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From all I can tell from experiences across the Veil and conversations with Higher Self, it is the Higher Self who makes this determination Pre-Life with the support and consultation of soul family, Guides and Angels.
There are several different potential exit points along the way that can be taken, otherwise one is in for the full ride one planned when connected with the fullness of oneself.
As to who is the 'Boss of Angels' - we don't know. We don't even know what Angels are. A decent guess is they are 5th and 6th dimensional beings.
That being said, there's a huge amount of races of sentient life living at the 5th and 6th dimension as well. So which ones are what humans call Angels? Do we consider most any Benevolent Being of higher Dimension an Angel?
Once when following my Grandmother O.B.E after she passed over the veil I followed her a good 20 dimensions before loosing her trail in pure light. So it's fair to say there's a lot of dimensions.
In other words an ant can't adequately describe the Empire State building and it's function in a larger society to another ant on the ground. We just don't have enough perspective to understand much outside our limited scope of perception.
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