There is an pervasive concept that the personality must die either immediately before awakening or as a result of it. This is not true. What happens is that the personality becomes "hollowed"; it is pervaded by emptiness and becomes like a hologram that you can see through its form. You, the witness, sees through your personality, and can choose to let it be in your life, or just hold it in silence.
So many teachers say the personality must die, but if you watch them, listen to them, follow them, you will find them filled with pettiness, vanity, giving themselves high rankings, or being rather thin skinned and defensive about their attainment or their teachings.
Robert was an amiable sociopath, always hiding motives and actions, manipulating people in the background, and he was the most profoundly entrenched in Nothingness than any other human I have ever met.
The personality is just mind and the interplay of mind and one's own sense of presence, of existence. Like the mind and the sense of presence, it can be watched, or allowed to function in this or that body.