There was no way I could have lived as a man with my old name. I also never liked it, so two strikes. Like Kylo, I liked starting fresh. I kept my initials the same but otherwise there's no similarity between my old name and my new one. Well, both middle names are a bit outlandish, but that's it.
Agree with Stone Magnum - settle on a name and change both your name and gender marker at the same time, or you'll get charged twice when updating documents the second time around.
Also agree with Alex. My parents wanted me to go slowly, even though they were supportive and understood that I had been waiting almost 8 years to have the resources to be able to transition. I do think it's usually because they hope we'll change our minds. I've made it through an entire medical transition in just over 2 years. It has been tough for them to keep up with because I've basically been on to the next thing every six months or so, but they did eventually fall in line and start getting things right consistently.
