The media we consume help to shape our worldviews. That's a scientifically-proven fact.
A lot of people describe gender transition as long and difficult and generally unpleasant. That's also a fact - there are fits and starts and lots of awkwardness and it's easy to become impatient with the whole thing. I can't say I'm completely immune to that stress, but being a geek has certainly put me in a place where the process is manageable. Here's what my geekdom has taught me:
We are not our bodies.
Geek media is full of transhumanism. As long as I can remember I've been absorbing stories about people who replace parts of their bodies, transform into fantastical creatures, or escape their physical forms entirely.
More importantly, these things are often seen as conscious decisions. In Ghost in the Shell: Stand-Alone Complex, Kusanagi is reminded by her teammates that she'd be a more formidable fighter if she chose a male prosthetic body. She tells them that she might one day but for now she enjoys being female (and let's face it, she's plenty effective as she is). Why shouldn't we also choose the bodies we want? Why wouldn't we?
When Tony Stark's body is made useless by a terrorist mastermind, he effectively builds himself a new one. Out of scraps. In a cave. In Afghanistan. When there's something wrong with your body, you fix it. A heart is hard to replace, but gender... that's practically a DIY project. You don't need to be a nuclear physicist or world-famous inventor to understand hormone replacement - just GTS and talk to your friendly neighborhood doctor.
100%-ing anything requires patience and perseverance.
I've got a friend who is playing through Final Fantasy Tactics. He's hacked the game to make all the characters into his friends, and he's picked builds which he things will make the characters reflect our personalities. (Evidently, I'm a Priest/Time Mage, but whatever.)
Watching him play, one of the things I am reminded of is how in JRPGs improving your characters often involves downgrading them now so you can upgrade them later. You might have to put a character into a lousy job or equip them with a crappy weapon in order for them to learn a powerful new skill. Sometimes you put your party into a state where they're struggling with even simple fights, often through hours and hours of grinding - but when it's done you can do amazing things and defeat any challenge.
Transition is no different than switching jobs in Tactics. At first you lose access to some of your old skills; everything is harder; you might have to run from some fights that you could have breezed through before. But you also see the progress bar ticking up every day. You watch the new skills and abilities light up. And eventually you max out the new job, pick your best skills from both classes, and kick butt for the rest of the game.
Transition makes you you, not someone else.
I don't recommend reading anything by Piers Anthony but if you have to, you could do worse than the award-winning A Spell for Chameleon, the first novel in his Xanth YA fantasy series.
Magician Trent's power is to transform any living thing into any other living thing. In the story, he transforms an ally, Bink, into a sphinx. He explains that he hasn't transformed Bink into an average sphinx, nor into some Platonic ideal of a sphinx, but rather into a "Bink-Sphinx" - a creature that only Bink could become. And if you read the book, you'll find out that Bink-Sphinx is pretty frickin' awesome.
When we transition, a lot of us look at the women around us and imagine we will (or should) look and act like them. That's one of the most harmful things we can do because it sets completely the wrong expectations. I'm not going to transform into the average gal I pass on the street. I'm not going to transform into the woman I would have been if I'd been born with two X chromosomes. I'm going to be the woman that only I could have become - the "Dave-Dana", if you will.
XX-Dana would probably have been shorter, slighter, girlier, probably straighter. Sure, she'd probably have been prettier, too. But you know what? I'm never going to be that person. I'm going to be tall, athletic, queer, butch. I'm going to be more handsome than pretty. And what I've come to realize - and appreciate - is that that's also pretty awesome. I've learned to embrace the body, voice, personality, and lifestyle I'm going to get to have. I'm looking forward to being Dave-Dana, because she's also going to be pretty frickin' awesome.
Though she is highly unlikely to fight any dragons...
[Note: I ended up turning out femme and reasonably pretty. That's what you get for engaging in speculation way before the fact. --Ed.]