Part of why im so drawn to Cicero is the infinite hunger for recognition/love that seems to stem from him being human, as well as the ever present denial of said recognition/love that stems from his role in the brotherhood.
There's this like. "catholic" guilt that's been baked into the very essence of his character (using the term catholic loosely bc i'm not religious in any way). Cicero craves the attention of the Night Mother, but he immediately denies himself this desire to be seen and appreciated for his efforts, because he is not the one who is "worthy" of all of that. He's a vital part of the order and he knows that! Without the Mother, they wouldn't have a link to the Dread Father. Of course, the rest of the brotherhood is also important; without the listener, they'd have no link to the Mother; without a speaker to redistribute the contracts, the order would be running on hopes and dreams; without the siblings, the order would be an idea and not a living, breathing organisation...
It's really interesting how Cicero is both the ideal member of the order (pious, takes care of the matron, is loyal to the tenets) and an absolute freak (prideful, no disregard for his fellow siblings, would kill the listener if there was no other way). I like to believe that he was actually chosen by the Mother-- he had to have been elected to get the title of the keeper, so it's not like he just likes to do it for fun. If we disregard the fact that they just needed a narrative continuation of the db in skyrim, he survived the destruction of the order in cyrodiil and managed to make it to skyrim to continue their legacy. He survived ten years hidden in some cavern or whatever with the Mother and as a result, went mad. Or at least partially mad, because he displays some VERY real moments of lucidity in certain parts of the game (the switch between third and first person; addressing himself as Cicero but still somehow talking about himself using pronouns like I/me or the possessive my). Maybe the Night Mother "gifted" him the Laughter, the Jester in his head so he wouldn't feel so alone? To add to the "chosen one" thought, if you summon the spectral assassin (Lucien) before your confrontation with Cicero in Dawnstar, he mentions that the Dread Father wouldn't want him to be killed or something along those lines
