I'm a tad gender-blind. I tend to have a harder time reading genders. I don't think I actually realized that boys don't wear skirts until I got to kindergarten. (I still think something incredibly pivotal happened that year and I have NO IDEA WHAT) And even now, when I wear skirts, it's got nothing to do with dressing like a girl. I just like skirts, they're fun, and they don't show your figure as much (at least not the ones I wear). I only wear them where it's okay for guys to wear them, too, so you don't get called a girl for it. Like on halloween or at cons.
So, because of this, I don't always have the best grasp on who does waht. And anything I did as a kid that seems girly I notice and amplify as "gah, I'm such a girl" and anything I did that isn't girly or is boyish I dismiss as "everyone did that".
It's not like I'm worried I'm not a boy, I know what I am. But transitioning when you can't convince a therapist you are? Or when you feel like even other transgenderists won't take you seriously? That seems like it'd be hard.