I think I sort of get where you're coming from, Kyle.
I haven't been able to start HRT (though I will schedule an appointment to get that ball rolling pretty soon), and I haven't yet changed my name or the gender marker on my license, but still I've begun to disconnect from my birth name and sort of rebuild myself as Noah.
I also was one of the fortunate ones who was allowed to do pretty much as I wished as a kid as far as gender goes, with very few exceptions. So I've more begun processing my past to fit the person I'm working on now than disconnected from it all really (though I know, had I been the proper sex beforehand, my past as a "real boy" would have likely been quite different in some respects). But I am disconnecting from the name I was given because I don't want to associate with it and I don't want to react any time I hear it, especially as it's a pretty common name.
I don't know what I might someday do with my high school diploma...maybe I'll let my parents keep it, I don't know. The other day I did toss my cap and gown from high school though as they were color coded, so to speak, according to "gender." Maybe had I come out years ago I could have had a maroon cap and gown and been proud to keep it, but now instead I just have my tassle hanging up to commemorate graduation. I'm not sure I'll keep any of my awards or anything with my given name, but I imagine I will be proud of anything with the right name on it, which makes it all the more important to have that changed before I get my associate's degree.
I have changed a little bit as Noah, being able to be Noah, but it's been for the good. I'm doing better, and if I have to disconnect a bit from certain things in order to continue to do so and continue to be who I want to be, who I really am, then I don't see it as anything to grieve. That was not really who I was supposed to be anyways. I can understand people grieving for who they were or had to be, because as others have said before it was a major part of one's life, but I guess for me it's been a little more like getting rid of someone in my life who was holding me back a bit or impacting me negatively...and I've never really grieved that.
I'm working on freeing myself, and the more I can disconnect from that name and what it holds the freer I'll be.