I went a year or two changing names and driving everybody insane in the process. I really liked Matthew but everybody called me Matt (hated that and got sick of correcting people), really liked Logan but it was too "bro-ish", I liked Zane but tired of it quickly, used Sebastian for awhile but my mom hated it (people called me Bastian and she said it sounded like bastard, lol). My friends and family were very nice and accommodating while I tried to find something that fitted me.
I always liked gender neutral names growing up like Taylor or Casey but when I had my name changed legally I wasn't passing often and thought a strong male name would help me pass.
I remember the first time I heard the name Simon. It was the youngest son's name on the tv show "7th Heaven" and I thought it was a nice name. I grew up watching the show with my mom and didn't know that the name was a common one in the UK but unusual in the USA.
After awhile I gave up on choosing a name for myself and wanted to do an official name change in the courts. I wrote a list of names I could live with and my mom chose Simon. I chose Vincent as my middle name simply because it flows well. My last name is my great grandma's maiden name but is a common one.
The funny thing I never noticed until it was pointed out is my chosen name is almost reversed from my birth name. My birth name was Dawn Simpson (no, I don't care who knows. I haven't used that name in 14 years. It feels like it was never mine.) and my name now is Simon D.
I kinda miss being able to play around with names. I think that is one of the more fun things about being trans.