Well let's see... When I was a teenager I asked my mom what my name would be if I was born a girl. She said she was going to name me Penelope and call me Penny for short. She was filling a big jar full of pennies to give to me. She had not even picked a boy's name, and instead my brother named me David. It's a nice name, and I always liked it.
So all throughout high school I wrote Penelope on everything. My friends thought I was weird.

But that's not the name I'm using. It just doesn't feel like me.
About 20 years ago I came up with the name Raven Moon. I do not know where I got it from. It just popped in my head one day. I knew I was Raven Moon. (I've been into the occult since I was about 12, and that's my witch name.) I've used that name in conjunction with my birth name online for a long time. When I recently made the firm decision to transition, I dropped my birth name from it in many places. Two of my close friends now call me Raven.
So Raven it is. Was there anyone born in the late 50s with that name? I really doubt it. Do I care? Not one tiny bit. When I looked at popular names from the 50s I only saw two I would even remotely consider. And one of them was the same as an ex girlfriend, and that's kind of creepy because we are still friends. lol Some people do change their names after all. It's also similar to my birth name sound wise. It's a cool sounding name, and it fits my personality.
Plus, I've always stuck out like a sore thumb, so it's fitting. I'm artistically a non conformist. People see me and know I'm either an artist or musician. Just last week my ex wife told me that someone from our daughter's school said to her that he saw her daughter with a man at the school, and was that OK? (my ex is black, so that might have been why he asked, but out daughter does look mixed). She said "Did he have blue hair? That's her dad!" lol
Also, I'm a musician, and plan to continue to perform until I can't. I play in an alternative grunge/punk band in NYC, so the name and my future persona will fit right in.

I'll be a cool middle aged rock goddess. lol I have come up with an elaborate last name too, but I'm not sure I'm going to change my last name. But it will be my stage name. Middle name? What the heck, might as well be Moon.

But I might use Penelope to honor my mom. She was the coolest, and also a singer back in the big band era. And we look alike.
I have no qualms about losing my initials or anything else. I'm putting that person to rest. I will always remember who I was, and I will soon become a different person. In a lot of ways we are free to invent our new persona, so I wanted to invent something memorable.

It might even give my musical career one last big boost. it also makes up for missing out on growing up super cute.