The caterpillar - butterfly thing is interesting. I wonder if a butterfly retains any caterpillar memory, or if it is a clean slate. That really would be two lives, only connected by physical material. Like me and so many other creatures that came before that used these atoms. Well, I guess the like the creatures I've consumed too.
What I know now, is that a good career is fulfilling on a level, provides financially and gives you enough time to pursue your passions. A great career IS your passion. I have a "good" career. I think the younger version of myself would approve. Also, in a previous post (I forget where, perhaps you can remind me) @mk mentioned that one of the gifts of aging is "self confidence" or a lack of insecurity... I forget the phrasing. Either way, you are totally right. I think our younger selves would be impressed with how confident we are. Don't you?
I would like to think I pass the younger self test. The teenage mk would be the most critical, of course. I was very sensitive to hypocrisy at that time, and I don't think I'm guilty of much. I like my current job. I'm not sure I see a great career as my passion, however. I think I see it as one that enables me to be more of myself, and perform less duties that aren't of my design. Maybe I just say that because I don't have so much of a singular passion, but get jazzed about so many different things. I don't know about the confidence thing. I think my younger self and I traded some confidences. It's an interesting thought.