I’ve come to the conclusion that bosses want their employees to become managers for the same reason parents want their kids to have children. It's not just the obvious reason that they seek to extend their line and influence beyond what they themselves can do in a flat hierarchy. They seek the schadenfreude of seeing the subordinate suffer as the subordinate made them suffer.
Dear former Chief Pilots,
I am truly sorry for any time I needed to be reminded to give you my medical renewal, PPC report, completed exams, or any other bit of paper you have to keep track of. I had no idea of how much of a pain it was.