The realization of being transgender came to me in the spring of 2011. From that point forward, I thought about transitioning non-stop for eight months. It was the number one topic on my mind during that time, and I did so much reading and research and watching videos. Like someone else said, one of the biggest factors in my decision was just seeing how many people could do it (and have done it) successfully. There are many more reasons; I could talk for hours (and have done so with my former psychologist) and must stop myself from writing an endless wall-of-text here. Having finally accepted that I'd never really connected with masculinity, that my friendships with guys were based on things other than feeling like "one of the guys," that I'd always (even if only unconsciously) related better to women than to men, among many other revelations, I was able to make my decision to transition because I realized that I couldn't stand the thought of living as a man (or trying to be a man, to be accepted as a man) for the rest of my life. Then I felt that my transition couldn't start soon enough. Even if the road is rocky in the beginning (and may well be for several years), why wouldn't you want to prolong, as much as possible, the time that you'll spend living the way that makes you the most happy? In other words, you should consider how much you might regret not starting earlier, once you're on the other side.
I'm deeply saddened that anyone ever has to think of transition as an absolute last resort out of fears of "going through hell." What that does is shift the onus entirely onto you; you have to be responsible and take the fall for other people's prejudices. But why should it be like that? If there weren't so much transphobia and other forms of bigotry in the world, then transition would be a no-brainer for most. Remember that fear is one of the most powerful methods of control. That's why terrorists are often so effective. But that's also why the right thing to do is having policies like not negotiating with terrorists. No good ever came from succumbing to fear and letting others control you through fear. Although nobody will fault you for choosing the path of least resistance, please don't forget that the other choice, the choice of taking a stand, is not only a way to help yourself but also others (however indirectly) who may be in situations that are similar to yours. Please consider why so many gay people have chosen to come out at great personal risk: It's the best way, perhaps the only way, to change the hearts and minds of homophobic loved ones who don't otherwise know any gay people personally. And you know what? It has worked.