What obstacles might be for a person to admit that he/she is transgender:
1) The most important obstacle is person's/child's identity, that is being hit from very early age, starting just after the birth. However, according to studies the child begins to understand his body a little later, from 7-9 months (one of the possible article as a source - Ages and Stages) and see themselves as a separate individual (as well as understand their own sexuality) from 2- 3 years. If you look at transgender people stories, usually they mention similar - 2-4 years age, when they clearly realised that something is wrong and what gender they have in their own understanding and feelings.
In a world I find increasing stories, when the child's voice starts to be taken very seriously at the early age, if not at 3 years age, then later on. While the kid is continuously suffering pushed stereotypes (body sex necessarily have to conform with the mind gender), parents finally begin to doubt their righteousness and eventually are accepting child's knowledge of the truth. It pleases, not many parents are both conscious and educated to seriously pay attention to the little ones. Of course, there are only a few of the parents who took it really easy and quickly. I think here are working both mechanisms: societal immaturity plus parents' traumas that were never healed and those prevent them to realise that the child owe nothing to them, and they have assumed full responsibility to give absolutely everything possible to their child.
It i soften said that parents fear for transgender child, as if he lived in a very large surrounding dissent ... And it is truth, the public is not ready, but! Public is not ready for large numbers of things that a child can learn in safe and secure home: think independently, to understand that his emotional world is unique and undisputed, learn to choose, to enhance his own self, learn empathy, learn to play and play and play, to understand personal boundaries, learn non-aggressive communication and so on, not to mention taking responsibility, philosophy, healthy diet, the same evaluation of both gender, and similar ideas/constructs. Society will condemn such a child - growing human, but at the same time he/she will be stronger than outside obstacles because such a child will be a strong within, more resistant on his/her own and he/she will have a strong backing at home. How do you think: if a child, transgender or not, does not have support at home, and even, if in the school is somewhat better for him, will he be able to withstand bullying and violence? Will he be an easy target for bullies: other aggressive children and adults? Often we do not have support and understanding at home as we grow and we search for it in the outside world, but since we didn't have a good example, so we choose similar types of people as in our household, and we pay for it.
But if going back to the idea of transgender man: such a person usually, according to current statistics suffers from natural identity rejection and breakage from the very young age and because of the need to be protected and loved, he/she must learn to avoid the show, talk and otherwise express them-selves, their true selves. This person must learn to dress and act by opposite gender stereotypes attributed to people. Such a person is very often punished for what he/she simply is, if they say it openly or suggest it in other ways: not wishing to wear particular clothes, to play particular games, interact with certain people in certain ways and loads of everything else. They are penalised for being them-selves and awarded for the absence of it. Over time, this mechanism becomes more complex, the child begins to understand that this will not change, he begins to live in his own world, to behave more aggressively and begins to be closed in other ways in order to resist against environmental injustice and try to keep his true-self. When you are small and can not survive alone, and others are repressing you for being your-self in many ways, it creates very high extra load and suffering. Undoubtedly frequently misunderstood transgender child may have a set of problems in school, among peers, and so on. However, what I would like to say and to emphasise to all those, who have grown and known their identity, that you were/are heroes that weathered everything as you grew, and you are still here alive :) This is really incredible.
Another thing I would like to mention, that from my own experience and observations of other people, I can say that the self-defence mechanisms can get so strong that you can learn to vary and manage your mind/feelings and everything else in a way that would help you to push out conscious understanding, sense of own identity. Or maybe to hide it, I do not know for sure, it's like trying to avoid it, to assume that this is sort of bad thing; maybe not the worst thing that can happen, but seriously major bad thing. Low, scurvy, just bad, false, incorrect, etc., you may feel that you will die, if you will be yourself. Even if you already have accepted, who you are, this doesn't mean you will not have those thoughts, that you are evil just because, you are, who you are. All this is merely an echo of the voices that were assuring you of these thought for a long time. But now it's different, now you are an adult and can tell those voices to go to hell or not pay attention to it. No one is born bad, that's a fact.
Another short note: that kind of parenting (refusing to take your child realistically) causes fragmentation of the personality for him. You have to play that you are someone, someone else, some roll, some fragment of your mind that is less significant and strong in you. I.E.: all men can play women, behave feminine, just as women can play men. But in this situation you are forced to live in this state constantly: forced to be an actor for live while living your life as well - solving various real life problems as everyone else around. So: 1) you must always remain not being you, your-self, 2) have an additional burden on an ongoing basis. You can't possibly avoid psychological problems in this state.
More about the mind gender construct in the next texts.
This is my blog about self-knowledge, self-work, emotional healing, growth, psychology, philosophy in general and other related themes.