Hi,
I understand exactly were you are coming from... I used to be very dependent on my ego in terms of a feeling of self worth that required hard work, beeting myself up and believing that I was in a competition with everyone. I would remember and analyse events that happend, most involving others to the point of madness. No suprises I was pretty depressed and lived a kind of paranoid existence.
I would describe this as simply not knowing any better - living completely identified with everything my mind told me and as it turns out living in the past and the future.
Initially all it took was reading a few books and realising that I was not my thoughts and in fact I could watch them. I gave myself permission to trust in what is and now meditate often. I feel like things are clear and visible, like always breathing fresh air and when something bad happens, which it did recently and people were panicking I became insanely calm, everything slowed down and I new exactly what to do - this is my target for the rest of my life.
However, I have periods of confusion like you discussed, lasting around a day to a week were I feel that I may have let go of something essential, that I am making a big mistake. At this time my mind goes mad, I can be aware of this, however, I don't like what I find. Can I live my life like this or is something essential missing?
One such thought is that presence is great, I feel that this calm is not who I have been all my life and hence I have lost touch with other aspects of my life such as career and direction. It is either that I have been kidding myself that I am good at something and yet with presence I really could not care and see this pursuit for what it truly is... an escape from reality... creating an image for myself... wanting to be somebody that I don't really care for...
Sorry if I have piggy backed on to this post but I am new to this game and it I understood exactly what you are going through.