There is never dialogue (flow of meaning) between ego and true self, as true self arises as ego dies.
Ego is always dysfunctional, collective ego is enhanced dysfunction.
It appears the "habit" Doug's ego is identifying in story as "money", speaks to the concept of "Pain-body" explained by Eckhart Tolle. Ego is not real, it is story. True self is not "habitual".
Woodchuck Pirate
aka Raymond J Raupers Jr USA