I came across Steve's blogs and podcasts where I think he used "I"(or "You") for speaking about different things. I don't blame him for that, tho. It's normal, it's probably mostly the consequence of a language limitation.
I believe that there can be (at least) 2 "I"s. Like: I as a person, or I as existence (being, life).
Philosophically, I is a difficult thing to describe, probably impossible.
If you read
Meditations, you'd know that Descartes tried to reason thoroughly, putting away all the unclear beliefs. He at a point came to the basic "true/correct" conclusion that he exists, because someone has to experience things... someone is the thinker (
I think, therefore I am.).
Now here I think D. was not being thorough enough. If you see a chair, all you can say
without a doubt is: there is an experience of a (thought of a) chair. That's it.
So where the hell does "I" come from??? Its existence doesn't make any logical sense.
Regarding personal development: Here, the confusion is between the person(ego) and the self as something greater than that. It can become confusing when you start talking about subjective reality. But then, especially when it comes to SR, I'd say that we (Steve included) can agree that "I" is something bigger than the mere person, it's more like existence, or precisely existence.
In that regard personal development is just developing a (small) part of yourself. So that when "you" as a certain person become wealthy (or whatever) it's not the "real" you who has become wealthy. So why are you trying to make this person (the not "real" you) wealthy? I don't know, people do a lot of crazy stuff.
(
Seriously, you have answer this question to yourself.)