This is a fun idea with a good premise.

And you must have known you were going to be critiqued here on your choice of philosopher :)

If my AI tells me I must overcome myself, reconcile with myself, find truths, and laugh, and do each of these things ten times each day - and tracks it for me so I know when I can stop developing and will sleep well... then we are talking Nietzsche! - Thus Sprach Zarathustra, The Academic Chairs of Virtue (II)