Overachiever here, and proud of it. And no, transitioning will not pave the way for further success for me. In my mind, I am successful because I do what I want, when I want, and don't worry about superficial things such as what other people will think of my actions. This, of course, is not to say that I don't care about others' feelings; of course that's not the case. If I could, I'd make a point of it to allow every person on earth to live his/her own dreams.
That said, I wasn't a failure at being female. Of course, I'm not quite certain what the definition of being female is. Did I look pretty and whatnot with a skirt and blouse? Sure. But I felt awful in that get-up. Did I attract men, and even date many? Yeah. Sad to say, but I did. It was all to cover up for the fact I knew I was different, but I did it. I've even dated quite a few guys who I would say were my ideals... not as boyfriends, but as men I'd like to be. I excelled in school, which I could just have easily done as a man, made good friends, worked decent jobs, and even fell in love with a couple amazing women who to this day I swear loved me back.
So being male, as I know I truly am, doesn't mean that things will improve. In fact, I may even suffer some shortcomings from the fact I will be, externally, a man... no more people opening doors for me, nobody picking up the tab after a dinner date, no free taxi rides... but I figure it's about the same. Ambition is ambition, and while having to stumble through my first 24 years as a female hindered me slightly due to the uncomfortableness of it all, I overcame it. It's no different with my being TS. There's nothing wrong with being female. I love women; I'm almost to the point of worshipping them. But I'm not one. That I know quite well. My ambition, my striving to overachieve, will remain, as always, regardless of transition.
Anyone who says otherwise just doesn't understand what it's like to know themself.
Rafe