You are very well-spoken, sensitive, and insightful. I'm not sure that you realize it. It is a beautiful thing to see in a person.
I think your position is very tough to be in. You're basically waiting for your life to start and comparing yourself to the people who you think are more successful than you are. We each have our own journey and there just isn't a correct way to travel it.
I don't want to go too far into mine since you wrote a lot of stuff here that I want to respond to, but I will mention that I took the "correct" path in life. I worked my *** off in school to worsen my mental state, get good grades, land a scholarship, go to college, and work myself into insanity. Was it ambition? No. I was frantically running to put distance between me and my childhood. I didn't see that though. In my desperation to just get away from the pain and suffering I felt, I completely ignored what I truly needed to grow as a person. I got out of college and felt directionless. I was afraid to fail and become the worthless person my father always told me I was. I denied my worsening condition and hid my feelings and my increasingly suicidal state until 2 years ago, I snapped and attempted suicide. I couldn't handle the numbness anymore. I hated feeling like a massive failure... Like i was setting everyone up to expect great things from me and I just couldn't deliver it. I had become convinced that the pain was going to last forever and I wasn't capable of getting better. I realized after almost dying that I hadn't wanted to die all along. I just wanted to feel loved and accepted and to not feel the pain and numbness anymore. That close encounter with death was NOT worth the realization. That realization could have come at any time if I had just taken a moment to piece it together. Like I said, I was in such a frantic rush away from the problem that I didn't see that I was running headfirst into a bigger problem.
I don't think you truly want to die either. I mean, your life still has so much potential. You're clearly a very thoughtful person (as in, you think a lot), but you live inside your own head so much that maybe you're not seeing the forest for the trees. You're not defective; you just aren't giving yourself the credit you deserve.
You don't HAVE to jump at a relationship with the first person who is nice to you and you are not weird for not wanting to do that. You need some time to get out there and live life. There is nothing wrong about it. I'm sure this girl is very nice, but there are lots of nice girls in the world. Realizing that a relationship is not right for you at this moment makes you that thoughtful person I just said you were. At your age, it's actually something to be proud of.
I think maybe working on what you want your long-term game to be would be the best start. Have you considered perhaps looking at a certification program? There might be something you can do that doesn't require a 4-year degree, but can help you get a leg up. You don't have to pick a career right this instant. It will change. My husband went to college for art, and guess what? All of those jobs dried right up and he's back in school for programming. You can always shift gears later on.
As for transitioning, surgery would be way down the line anyway, so there's no reason you can't start reading up and figuring out what you want to do with your life. Before you even get close to the surgery, you have to talk to a counselor, do hormone therapy, and all of that. Don't worry about what people say about you being an ugly girl. That's what makeup is for (joking). I know it's a lot harder when you are already feeling very insecure about your identity to hear those kinds of things, but honestly, people have no idea what anyone would actually look like as the opposite gender until they see it.
I'm sorry that you live in a less understanding area, but there are other areas that might be prime for a fresh start. It's not going to be easy to make such big changes in your life, but it's all about baby steps. Just try to break it up into little pieces. You'll make it.
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